2554:
491:
333:
109:
95:
71:
1679:
1089:
1329:, which rank amino acids from most hydrophobic to most hydrophilic, consistently place cysteine towards the hydrophobic end of the spectrum, even when they are based on methods that are not influenced by the tendency of cysteines to form disulfide bonds in proteins. Therefore, cysteine is now often grouped among the hydrophobic amino acids, though it is sometimes also classified as slightly polar, or polar.
5268:
1348:
979:
1368:. Cysteine residues play a valuable role by crosslinking proteins, which increases the rigidity of proteins and also functions to confer proteolytic resistance (since protein export is a costly process, minimizing its necessity is advantageous). Inside the cell, disulfide bridges between cysteine residues within a polypeptide support the protein's tertiary structure.
742:
3524:
Eriksson, C J Peter; Metsälä, Markus; Möykkynen, Tommi; Mäkisalo, Heikki; Kärkkäinen, Olli; Palmén, Maria; Salminen, Joonas E; Kauhanen, Jussi (20 October 2020). "L-Cysteine
Containing Vitamin Supplement Which Prevents or Alleviates Alcohol-related Hangover Symptoms: Nausea, Headache, Stress and
1460:) produced by the respiratory chain can react with the cysteine residues in these complexes, leading to dysfunctional proteins and potentially contributing to aging. The primary response of a protein to ROS is the oxidation of cysteine and the loss of free thiol groups, resulting in increased
1312:
groups in the side chains of other polar amino acids. However, the cysteine side chain has been shown to stabilize hydrophobic interactions in micelles to a greater degree than the side chain in the nonpolar amino acid glycine and the polar amino acid serine. In a statistical analysis of the
3825:, previously ascribed to cystine, is ascribed. In order to indicate the relationships of this substance to cystine, I name this reduction product of cystine: "cysteïne".) Note: Baumann's proposed structures for cysteine and cystine (see p.302) are incorrect: for cysteine, he proposed CH
1035:
of animal materials, such as poultry feathers or hog hair. Despite widespread rumor, human hair is rarely a source material. Indeed, food additive or cosmetic product manufactures may not legally source from human hair in the
European Union.
1359:
Disulfide bonds in proteins are formed by oxidation of the sulfhydryl group of cysteine residues. The other sulfur-containing amino acid, methionine, cannot form disulfide bonds. More aggressive oxidants convert cysteine to the corresponding
1313:
frequency with which amino acids appear in various proteins, cysteine residues were found to associate with hydrophobic regions of proteins. Their hydrophobic tendency was equivalent to that of known nonpolar amino acids such as
1003:
foods. Some foods considered rich in cysteine include poultry, eggs, beef, and whole grains. In high-protein diets, cysteine may be partially responsible for reduced blood pressure and stroke risk. Although classified as a
1955:
Semenza, Evan R.; Harraz, Maged M.; Abramson, Efrat; Malla, Adarsha P.; Vasavda, Chirag; Gadalla, Moataz M.; Kornberg, Michael D.; Snyder, Solomon H.; Roychaudhuri, Robin (23 Sep 2021) .
2213:
1464:
and associated protein cross-linking. In contrast, another sulfur-containing, redox-active amino acid, methionine, does not exhibit these biochemical properties and its content is relatively upregulated in
1213:. While glutamic acid is usually sufficient because amino acid nitrogen is recycled through glutamate as an intermediary, dietary cysteine and glycine supplementation can improve synthesis of glutathione.
5802:
1420:
often function with the help of a catalytic cysteine. These roles are typically limited to the intracellular milieu, where the environment is reducing, and cysteine is not oxidized to cystine.
963:
chirality, because of the presence of sulfur (or selenium) as a second neighbor to the asymmetric carbon atom. The remaining chiral amino acids, having lighter atoms in that position, have
1205:, which occurs in humans and other organisms. The systemic availability of oral glutathione (GSH) is negligible; so it must be biosynthesized from its constituent amino acids, cysteine,
3311:
Moosmann, Bernd; Hajieva, Parvana; Behl, Christian (2006), "The antioxidant function of protein methionine explains about the evolution of a non-standard genetic code in mitochondria",
3481:
Sprince H, Parker CM, Smith GG, Gonzales LJ (April 1974). "Protection against acetaldehyde toxicity in the rat by L-cysteine, thiamin and L-2-methylthiazolidine-4-carboxylic acid".
3950:
755:
1489:
in the food, pharmaceutical, and personal-care industries. One of the largest applications is the production of flavors. For example, the reaction of cysteine with sugars in a
5224:
5581:
2019:"Amino acid names and parlor games: from trivial names to a one-letter code, amino acid names have strained students' memories. Is a more rational nomenclature possible?"
1925:
1336:, which play an important role in the folding and stability of some proteins, usually proteins secreted to the extracellular medium. Since most cellular compartments are
5795:
3389:
Otoyama, Ippo; Hamada, Hironobu; Kimura, Tatsushi; Namba, Haruchi; Sekikawa, Kiyokazu; Kamikawa, Norimichi; Kajiwara, Teruki; Aizawa, Fumiya; Sato, Yoshinobu M. (2019).
867:-cysteine acts as a signaling molecule in mammalian nervous systems. Cysteine is named after its discovery in urine, which comes from the urinary bladder or cyst, from
1621:
to produce wool. It is an essential amino acid that is taken in from their feed. As a consequence, during drought conditions, sheep produce less wool; however,
3648:
Milkowski, John D.; Veber, Daniel F.; Hirschmann, Ralph (1979). "Thiol
Protection with the Acetamidomethyl Group: S-Acetamidomethyl-L-Cysteine Hydrochloride".
5788:
1249:
Beyond the iron-sulfur proteins, many other metal cofactors in enzymes are bound to the thiolate substituent of cysteinyl residues. Examples include zinc in
550:
3943:
1390:, which oxidizes the environment. In this environment, cysteines are, in general, oxidized to cystine and are no longer functional as a nucleophiles.
1824:
3266:"Thiyl Radical Reaction with Amino Acid Side Chains: Rate Constants for Hydrogen Transfer and Relevance for Posttranslational Protein Modification"
5217:
2137:
2056:
5574:
5517:
1815:
223:
5997:
5168:
4479:
3348:
2615:
2513:"Deficient synthesis of glutathione underlies oxidative stress in aging and can be corrected by dietary cysteine and glycine supplementation"
2378:
2361:
Drauz, Karlheinz; Grayson, Ian; Kleemann, Axel; Krimmer, Hans-Peter; Leuchtenberger, Wolfgang; Weckbecker, Christoph (2007). "Amino Acids".
1321:(tyrosine is polar aromatic but also hydrophobic), those of which were much greater than that of known polar amino acids such as serine and
6310:
5901:
3936:
2847:
5906:
4535:
3613:
Powell BC, Walker SK, Bawden CS, Sivaprasad AV, Rogers GE (1994). "Transgenic sheep and wool growth: possibilities and current status".
2713:
1008:, in rare cases, cysteine may be essential for infants, the elderly, and individuals with certain metabolic diseases or who suffer from
6564:
5210:
1372:
is an example of a protein with cystine crosslinking, wherein two separate peptide chains are connected by a pair of disulfide bonds.
2822:
959:
system of designating chirality, based on the atomic numbers of atoms near the asymmetric carbon, cysteine (and selenocysteine) have
5567:
3731:
1849:
1794:
505:
1892:
1444:, cysteine exhibits strong nucleophilic and redox-active properties. These properties contribute to the depletion of cysteine from
4944:
1633:
Being multifunctional, cysteine undergoes a variety of reactions. Much attention has focused on protecting the sulfhydryl group.
6594:
6569:
6132:
5067:
3451:
Interaction of alcohol and smoking in the pathogenesis of upper digestive tract cancers: possible chemoprevention with cysteine
1933:
1539:
Cysteine has been proposed as a preventive or antidote for some of the negative effects of alcohol, including liver damage and
1394:
932:
1519:
Cysteine is a very popular target for site-directed labeling experiments to investigate biomolecular structure and dynamics.
384:
212:
3905:
2476:
Bulaj G, Kortemme T, Goldenberg DP (June 1998). "Ionization-reactivity relationships for cysteine thiols in polypeptides".
6161:
4295:
1015:. Cysteine can usually be synthesized by the human body under normal physiological conditions if a sufficient quantity of
3074:
Giles, Niroshini M; Watts, Aaron B; Giles, Gregory I; Fry, Fiona H; Littlechild, Jennifer A; Jacob, Claus (August 2003).
762:
6291:
5507:
3364:
1055:
laws, is also available, albeit at a higher price. The typical synthetic route involves fermentation with an artificial
440:
2296:
6589:
6574:
6469:
6002:
5185:
4769:
4496:
1528:
1375:
1189:
form in the cell. Because of its high reactivity, the sulfhydryl group of cysteine has numerous biological functions.
1124:
1093:
469:
3756:
2321:"Regulation (EC) No 1223/2009 of the European Parliament and of the Council of 30 November 2009 on cosmetic products"
3570:
Kanter MZ (October 2006). "Comparison of oral and i.v. acetylcysteine in the treatment of acetaminophen poisoning".
1043:-cysteine as a food additive contravene kosher, halal, vegan, or vegetarian diets. To avoid this problem, synthetic
6559:
3911:
2308:...L-cysteine hydrochloride or hydrochloride monohydrate. Human hair may not be used as a source for this substance
1179:
668:
6358:
6266:
5992:
5941:
5916:
5291:
5120:
4977:
4669:
2088:
Lee, Jumin; Hitzenberger, Manuel; Rieger, Manuel; Kern, Nathan R.; Zacharias, Martin; Im, Wonpil (21 July 2020).
1820:
1132:
1097:
340:
1293:
In the translation of messenger RNA molecules to produce polypeptides, cysteine is coded for by the UGU and UGC
6479:
6286:
6142:
5921:
5233:
2332:...ANNEX II LIST OF SUBSTANCES PROHIBITED IN COSMETIC PRODUCTS...416 Cells, tissues or products of human origin
1445:
821:
4096:
5926:
3813:), however the new base can clearly be recognized as a reduction product of cystine, to which the formula C
6584:
6325:
6281:
6109:
5882:
5173:
4897:
4616:
4528:
4484:
4239:
4235:
4022:
4018:
1508:
applications, predominantly in Asia. Again, the cysteine is used for breaking up the disulfide bonds in the
1457:
1274:
1270:
2674:"A model for sulfhydryl groups in proteins. Hydrophobic interactions of the cystein side chain in micelles"
2553:
328:
6534:
6413:
6390:
6228:
6137:
6064:
5969:
5857:
5817:
5527:
5147:
5113:
4033:
3455:
2320:
1810:
6350:
6026:
5680:
5522:
5512:
5003:
4915:
3990:
1769:
1486:
1449:
1387:
1326:
1254:
1155:
277:
132:
3449:
108:
3171:
5825:
5814:
5726:
5532:
4591:
4568:
4181:
3859:
3402:
2751:
2434:
2145:
2064:
1971:
1649:
1383:
1337:
1117:
1005:
724:
101:
54:
1565:
dose of acetaldehyde. Those that received cysteine had an 80% survival rate; when both cysteine and
6526:
6315:
6007:
5987:
5732:
5336:
4847:
4326:
4200:
4014:
2395:
1735:
1230:
486:
162:
115:
3919:
5936:
5283:
5142:
5052:
4988:
4828:
4791:
4521:
3885:
3595:
3506:
2979:
2903:
2777:
2458:
2195:
2119:
1958:"D-cysteine is an endogenous regulator of neural progenitor cell dynamics in the mammalian brain"
1175:
1136:
5780:
2851:
1601:
is attached to the nitrogen atom. This compound is sold as a dietary supplement, and used as an
1428:
Cysteine is considered a "newcomer" amino acid, being the 17th amino acid incorporated into the
6474:
6432:
5738:
5640:
5617:
5547:
5369:
5047:
5037:
4962:
4954:
4907:
4884:
4862:
4156:
4005:
3985:
3877:
3737:
3727:
3675:
Arnold, Alan P.; Jackson, W. Gregory (1990). "Stereospecificity in the
Synthesis of the Tris((
3630:
3587:
3552:
3498:
3430:
3344:
3293:
3285:
3246:
3238:
3199:
3191:
3152:
3144:
3103:
3095:
3056:
3038:
2999:
2960:
2942:
2895:
2769:
2695:
2654:
2611:
2588:
2542:
2493:
2450:
2374:
2187:
2111:
2038:
1999:
1845:
1790:
1750:
1714:
1490:
1197:
Due to the ability of thiols to undergo redox reactions, cysteine and cysteinyl residues have
1159:
695:
94:
3338:
3337:
Huang, Tzou-Chi; Ho, Chi-Tang (2001-07-27). Hui, Y. H.; Nip, Wai-Kit; Rogers, Robert (eds.).
3218:
2717:
2584:
1784:
5982:
5862:
5768:
5756:
5750:
5693:
5644:
5623:
5094:
4920:
4820:
4401:
4260:
4206:
4048:
3867:
3719:
3696:
3657:
3622:
3579:
3542:
3534:
3490:
3459:
3420:
3410:
3320:
3277:
3230:
3183:
3134:
3087:
3046:
3030:
2991:
2950:
2934:
2885:
2759:
2685:
2644:
2580:
2532:
2524:
2485:
2442:
2407:
2366:
2179:
2101:
2030:
1989:
1979:
1875:
1866:"Nomenclature and symbolism for amino acids and peptides (IUPAC-IUB Recommendations 1983)",
1745:
1638:
1587:
1524:
1057:
825:
788:
647:
581:
76:
2801:
Amino Acid
Properties and Consequences of Substitutions, In: Bioinformatics for Geneticists
2243:"Like mountains hanging by a hair: Kosher issues in L-cysteine (Commentary on Chagiga I:8)"
1713:
found that when cystine was treated with a reducing agent, cystine revealed itself to be a
456:
449:
6579:
6276:
6084:
5152:
5107:
4724:
4361:
4068:
4053:
4037:
3980:
3972:
3923:
3793:(Analysis of the substance reveals values which approximate those required by cystine (C
3467:
2826:
2568:
2250:
1828:
1498:
1278:
1262:
305:
2344:
2167:
297:
187:
3863:
3406:
3324:
2755:
2438:
1975:
1900:
1174:
and easily oxidized. The reactivity is enhanced when the thiol is ionized, and cysteine
490:
332:
257:
179:
172:
6271:
5911:
5872:
5469:
5179:
5101:
5042:
5013:
4937:
4851:
4714:
4557:
4490:
4211:
4186:
4076:
3959:
3425:
3390:
3051:
3018:
2690:
2673:
2537:
2512:
1994:
1957:
1505:
1379:
1333:
1148:
972:
879:
868:
733:
682:
70:
5202:
3872:
3847:
3187:
3091:
2955:
2922:
2764:
2739:
2034:
1678:
1088:
6553:
6456:
6423:
6385:
6243:
6127:
5699:
5687:
5673:
5627:
5601:
5542:
5463:
5457:
5359:
5072:
4838:
4732:
4649:
4451:
4436:
4356:
4275:
4255:
4245:
4221:
4091:
4043:
3723:
3139:
3122:
2123:
1710:
1606:
1576:
In 2020 an article was published that suggests L-cysteine might also work in humans.
1570:
1466:
1461:
1365:
1361:
1210:
1128:
1009:
636:
321:
3928:
3889:
3791:) verlangten sich nähern, nenne ich dieses Reduktionsprodukt des Cystins: Cysteïn."
3219:"Sulfur and Selenium: The Role of Oxidation State in Protein Structure and Function"
2781:
2199:
6494:
6372:
6248:
6079:
6012:
5877:
5867:
5847:
5607:
5257:
4932:
4802:
4641:
4548:
4371:
4366:
4346:
4316:
4280:
4106:
4028:
3963:
3599:
3510:
2907:
2633:"Pharmacologic role of cysteine in ameliorating or exacerbating mineral toxicities"
2462:
2018:
1642:
1598:
1544:
1429:
1398:
1258:
1113:
909:
5931:
3391:"L-cysteine improves blood fluidity impaired by acetaldehyde: In vitro evaluation"
2370:
2255:
Rabbi Blech does not address hog hair-derived cysteine, which is almost certainly
1355:(shown here in its neutral form), two cysteines bound together by a disulfide bond
1076:
hydrolyzes racemic 2‑amino-Δ‑thiazoline-4‑carboxylic acid to
894:
is sometimes used. The deprotonated form can generally be described by the symbol
3415:
3217:
Jacob, Claus; Giles, Gregory I.; Giles, Niroshini M.; Sies, Helmut (2003-10-13).
2995:
2938:
2796:
2183:
1201:
properties. Its antioxidant properties are typically expressed in the tripeptide
429:
6224:
5613:
5501:
5434:
5062:
5033:
5018:
4892:
4704:
4664:
4626:
4446:
4411:
4321:
4311:
4270:
4231:
4191:
4136:
4010:
3714:
Anderson, Mary E.; Meister, Alton (1987). "Intracellular delivery of cysteine".
3075:
3019:"Cysteine-Mediated Redox Signaling: Chemistry, Biology, and Tools for Discovery"
1645:
1634:
1559:
1548:
1531:
for EPR or paramagnetic relaxation-enhanced NMR also uses cysteine extensively.
1402:
1332:
Most cysteine residues are covalently bonded to other cysteine residues to form
1305:
1301:
1266:
1250:
1234:
1202:
1198:
1171:
848:
5267:
1347:
1162:, using sulfide sources, converts this ester into cysteine, releasing acetate.
6504:
6380:
6345:
6335:
6320:
6301:
6200:
6195:
6190:
6089:
5977:
5956:
5829:
5811:
5631:
5537:
5378:
5354:
5311:
5300:
5088:
5023:
4993:
4777:
4757:
4747:
4631:
4576:
4456:
4441:
4421:
4416:
4406:
4396:
4386:
4341:
4336:
4331:
4290:
4216:
4121:
4116:
4111:
4086:
2242:
1740:
1730:
1622:
1482:
1453:
1441:
1433:
1314:
1226:
1109:
1069:
1032:
1016:
925:
658:
615:
563:
374:
288:
218:
3661:
3538:
3289:
3265:
3242:
3195:
3148:
3099:
3042:
2946:
2271:
2042:
924:
Like other amino acids (not as a residue of a protein), cysteine exists as a
6404:
6220:
6185:
6118:
6104:
5650:
5428:
5393:
5383:
5344:
4742:
4699:
4684:
4654:
4601:
4431:
4381:
4376:
4285:
4265:
4146:
4058:
3368:
2649:
2632:
2528:
1984:
1879:
1520:
1406:
1322:
978:
844:
3881:
3591:
3556:
3434:
3297:
3250:
3234:
3203:
3156:
3107:
3060:
3003:
2899:
2773:
2592:
2546:
2411:
2191:
2138:"Amber Workshop - Tutorial A1 - Section 1: Do some editing of the PDB file"
2115:
2057:"Amber Workshop - Tutorial A1 - Section 1: Do some editing of the PDB file"
2003:
3741:
3634:
3502:
2964:
2699:
2658:
2497:
2454:
2446:
6460:
6447:
6180:
6171:
6075:
6036:
5852:
5744:
5590:
5481:
5422:
5349:
4972:
4810:
4752:
4737:
4689:
4679:
4606:
4581:
4544:
4461:
4426:
4391:
4351:
4250:
4141:
4126:
4101:
4081:
4000:
3172:"Role of oxidative stress and protein oxidation in the aging process1, 2"
2569:"Iron-sulfur protein biogenesis in eukaryotes: components and mechanisms"
2214:"Cysteine - Health Encyclopedia - University of Rochester Medical Center"
1932:. University of Wisconsin-Madison Bacteriology Department. Archived from
1602:
1566:
1540:
1437:
1318:
1309:
1186:
1144:
1127:
then combines homocysteine and serine to form the asymmetrical thioether
1012:
968:
902:
366:
358:
43:
39:
31:
17:
3700:
3547:
2345:"Questions About Food Ingredients: What is L-cysteine/cysteine/cystine?"
1401:
sulfhydryl group allows cysteine to conjugate to other groups, e.g., in
6152:
6071:
6050:
6041:
5960:
5946:
5892:
5717:
5326:
5321:
5316:
5305:
5252:
5247:
4926:
4858:
4196:
3995:
3583:
3494:
3463:
1718:
1669:
1513:
1413:
1393:
Aside from its oxidation to cystine, cysteine participates in numerous
1369:
1352:
1341:
1238:
1222:
1206:
1147:, cysteine biosynthesis also starts from serine, which is converted to
1000:
887:
883:
416:
341:
47:
35:
3626:
3281:
3034:
2489:
2168:"Dietary Cysteine and Other Amino Acids and Stroke Incidence in Women"
2106:
2089:
1547:. It binds to acetaldehyde to form the low-toxicity heterocycle methyl
6257:
6055:
5838:
5416:
5388:
5295:
5134:
4226:
4170:
1893:"cysteine - Definition of cysteine in English by Oxford Dictionaries"
1417:
1409:
1282:
1105:
1065:
1048:
268:
4513:
2398:; Scherberich, Paul (1981). "Facile Synthesis of Racemic Cysteine".
732:
Except where otherwise noted, data are given for materials in their
2890:
2873:
2166:
Larsson, Susanna C.; Håkansson, Niclas; Wolk, Alicja (April 2015).
404:
4694:
4165:
4131:
3367:. U.S. Food and Drug Administration. November 2004. Archived from
3264:
Nauser, Thomas; Pelling, Jill; Schöneich, Christian (2004-10-01).
2980:"The origin of the genetic code and of the earliest oligopeptides"
2425:
Hell R (1997). "Molecular physiology of plant sulfur metabolism".
2257:
1618:
1346:
1294:
1140:
1052:
977:
913:
840:
686:
248:
222:
211:
201:
3771:"Die Analyse der Substanz ergibt Werthe, welche den vom Cystin (C
1660:
Relative to most other amino acids, cysteine is much more toxic.
5762:
1962:
1509:
395:
5784:
5563:
5206:
4517:
3932:
1304:
amino acid, based largely on the chemical parallel between its
5667:
1926:"The primary structure of proteins is the amino acid sequence"
1783:
Belitz, H.-D; Grosch, Werner; Schieberle, Peter (2009-02-27).
1673:
1555:
809:
524:
InChI=1/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
5559:
3848:"Strong hydrophobic nature of cysteine residues in proteins"
2874:"Formation and transfer of disulphide bonds in living cells"
2740:"Strong hydrophobic nature of cysteine residues in proteins"
1625:
sheep that can make their own cysteine have been developed.
474:
107:
93:
5637:
3340:
Meat
Science and Applications, ch. Flavors of Meat Products
3123:"Mitochondrially encoded cysteine predicts animal lifespan"
1844:(62nd ed.). Boca Raton, FL: CRC Press. p. C-259.
1185:
values close to neutrality, so are often in their reactive
3718:. Methods in Enzymology. Vol. 143. pp. 313–325.
2823:"Introduction to Protein Structure--Non-Polar Amino Acids"
3076:"Metal and Redox Modulation of Cysteine Protein Function"
2921:
Osawa, S; Jukes, T H; Watanabe, K; Muto, A (March 1992).
806:
797:
863:‑Cysteine is a protein monomer in all biota, and
1690:
1068:(formerly Degussa) introduced a route from substituted
750:
3916:
1416:, which engage in proteolysis in the apoptotic cycle.
2272:"VRG-News July 2007 -- the Vegetarian Resource Group"
990:)-Cysteine (right) in zwitterionic form at neutral pH
812:
800:
794:
359:
3017:
Paulsen, Candice E.; Carroll, Kate S. (2013-07-10).
1504:
In the field of personal care, cysteine is used for
1104:
In animals, biosynthesis begins with the amino acid
886:, which serves an important structural role in many
803:
514:
InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)
6525:
6518:
6492:
6455:
6445:
6422:
6403:
6334:
6300:
6256:
6241:
6209:
6170:
6151:
6117:
6102:
6049:
6034:
6025:
5955:
5891:
5837:
5824:
5443:
5402:
5368:
5335:
5282:
5275:
5240:
5133:
5080:
5032:
5002:
4971:
4953:
4906:
4883:
4876:
4837:
4819:
4801:
4790:
4766:
4723:
4663:
4640:
4615:
4590:
4567:
4556:
4304:
4164:
4155:
4067:
3971:
2923:"Recent evidence for evolution of the genetic code"
1432:. Similar to other later-added amino acids such as
1300:Cysteine has traditionally been considered to be a
1285:metals such as mercury, lead, and cadmium tightly.
791:
534:
InChI=1/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)
383:
3121:Moosmann, Bernd; Behl, Christian (February 2008).
2400:Angewandte Chemie International Edition in English
1237:is extracted from cysteine, which is converted to
878:The thiol is susceptible to oxidation to give the
1412:transfer ubiquitin to its pendant, proteins, and
641:240 °C (464 °F; 513 K) decomposes
1523:selectively attach to cysteine using a covalent
1340:, disulfide bonds are generally unstable in the
1277:, so that proteins containing cysteine, such as
428:
3846:Nagano N, Ota M, Nishikawa K (September 1999).
2738:Nagano N, Ota M, Nishikawa K (September 1999).
901:When used as a food additive, cysteine has the
186:
178:
171:
3687:)-Cysteinesulfinato-N,S)cobaltate(III) Ions".
2511:Sekhar, Rajagopal V; Patel, Sanjeet G (2011).
2363:Ullmann's Encyclopedia of Industrial Chemistry
5796:
5575:
5218:
4529:
3944:
2610:. Mill Valley, CA: University Science Books.
2606:Lippard, Stephen J.; Berg, Jeremy M. (1994).
1823:Dep't. of Biology, Chemistry, and Pharmacy.
1569:were administered, all animals survived. The
1135:converts the cystathionine into cysteine and
843:side chain in cysteine often participates in
8:
2631:Baker DH, Czarnecki-Maulden GL (June 1987).
2090:"CHARMM-GUI supports the Amber force fields"
1809:Kirste, Burkhard (23 Jan 1998). "
1920:
1918:
6522:
6452:
6253:
6114:
6046:
6031:
5834:
5803:
5789:
5781:
5582:
5568:
5560:
5279:
5225:
5211:
5203:
4880:
4798:
4564:
4536:
4522:
4514:
4161:
3951:
3937:
3929:
2517:The American Journal of Clinical Nutrition
2356:
2354:
2235:
2233:
1543:. It counteracts the poisonous effects of
489:
331:
304:
296:
59:
53:"Cys" redirects here. For other uses, see
3871:
3546:
3424:
3414:
3138:
3050:
2954:
2889:
2763:
2689:
2648:
2536:
2105:
1993:
1983:
455:
448:
2848:"Virtual Chembook--Amino Acid Structure"
2585:10.1146/annurev.cellbio.22.010305.104538
1641:. Treatment with formaldehyde gives the
1193:Precursor to the antioxidant glutathione
1087:
834:
830:
3223:Angewandte Chemie International Edition
1761:
1597:is a derivative of cysteine wherein an
1269:. The sulfhydryl group also has a high
555:
510:
485:
2978:Trifonov, Edward N. (September 2009).
2872:Sevier CS, Kaiser CA (November 2002).
1031:-cysteine is obtained industrially by
322:
5998:2-Amino-3-carboxymuconic semialdehyde
3761:Zeitschrift für physiologische Chemie
2083:
2081:
1842:CRC Handbook of Chemistry and Physics
1344:with some exceptions as noted below.
517:Key: XUJNEKJLAYXESH-UHFFFAOYSA-N
276:
256:
7:
6311:2,3-Dihydroxy-3-methylpentanoic acid
3917:International Kidney Stone Institute
2714:"A Review of Amino Acids (tutorial)"
2608:Principles of Bioinorganic Chemistry
2241:Blech, Zushe Yosef (May 2003).
5234:Encoded (proteinogenic) amino acids
3759:[On cystine and cysteine].
3325:10.1016/j.freeradbiomed.2006.10.015
2716:. Curtin University. Archived from
1221:Cysteine is an important source of
1039:Some animal-originating sources of
537:Key: XUJNEKJLAYXESH-UHFFFAOYAC
527:Key: XUJNEKJLAYXESH-REOHCLBHBU
419:
403:
2850:. Elmhurst College. Archived from
2795:Betts, M.J.; R.B. Russell (2003).
2691:10.1111/j.1432-1033.1968.tb19535.x
147:2-Amino-3-sulfhydrylpropanoic acid
25:
5661:Additional chemicals (E1100–1599)
3313:Free Radical Biology and Medicine
3176:Free Radical Biology and Medicine
1535:Reducing toxic effects of alcohol
1456:, since reactive oxygen species (
1378:catalyze the proper formation of
1217:Precursor to iron-sulfur clusters
1170:The cysteine sulfhydryl group is
1096:catalyzes the upper reaction and
1047:-cysteine, compliant with Jewish
967:chirality. Replacing sulfur with
5266:
3170:Sohal, Rajindar S (2002-07-01).
3140:10.1111/j.1474-9726.2007.00349.x
2552:
1677:
1652:upon treatment with metal ions.
1558:study, test animals received an
1395:post-translational modifications
787:
740:
599:
593:
69:
6133:Imidazol-4-one-5-propionic acid
3270:Chemical Research in Toxicology
2094:The Journal of Chemical Physics
999:Cysteinyl is a residue in high-
859:-cysteine are found in nature.
851:. Cysteine is chiral, but both
736:(at 25 °C , 100 kPa).
5947:β-Hydroxy β-methylglutaryl-CoA
5902:β-Hydroxy β-methylbutyric acid
1840:Weast, Robert C., ed. (1981).
1648:. Cysteine forms a variety of
951:-glyceraldehyde. In the newer
943:notation based on homology to
608:
602:
587:
1:
6162:1-Pyrroline-5-carboxylic acid
5907:β-Hydroxy β-methylbutyryl-CoA
3873:10.1016/S0014-5793(99)01122-9
3716:Sulfur and Sulfur Amino Acids
3365:"Food Ingredients and Colors"
3188:10.1016/S0891-5849(02)00856-0
3092:10.1016/s1074-5521(03)00174-1
2821:Gorga, Frank R. (1998–2001).
2765:10.1016/S0014-5793(99)01122-9
2567:Lill R, Mühlenhoff U (2006).
2371:10.1002/14356007.a02_057.pub2
2035:10.1016/s0307-4412(97)00167-2
1897:Oxford Dictionaries - English
1424:Evolutionary role of cysteine
1108:. The sulfur is derived from
1100:catalyzes the lower reaction.
6292:2-Methyl-3-oxopropanoic acid
3724:10.1016/0076-6879(87)43059-0
3416:10.1371/journal.pone.0214585
2996:10.1016/j.resmic.2009.05.004
2939:10.1128/mr.56.1.229-264.1992
2347:. Vegetarian Resource Group.
2249:. Vol. IV, no. 6.
2184:10.1161/STROKEAHA.114.008022
1497:-Cysteine is also used as a
1376:Protein disulfide isomerases
1074:Pseudomonas thiazolinophilum
6470:4-Hydroxyphenylpyruvic acid
6003:2-Aminomuconic semialdehyde
3960:Cough and cold preparations
2672:Heitmann P (January 1968).
1721:which he named "cysteïne".
1529:Site-directed spin labeling
1125:Cystathionine beta-synthase
1094:Cystathionine beta synthase
890:. In this case, the symbol
89:
6611:
6346:generation of homocysteine
5292:Branched-chain amino acids
3757:"Ueber Cystin und Cysteïn"
2297:"EU Chemical Requirements"
2017:Saffran, M. (April 1998).
1667:
1289:Roles in protein structure
52:
29:
6565:Proteinogenic amino acids
5993:3-Hydroxyanthranilic acid
5597:
5495:
5264:
5163:
5121:Prednisolone/promethazine
5102:Methylthioninium chloride
4474:
3454:(Academic dissertation).
3448:Salaspuro, Ville (2006).
2797:"Hydrophobic amino acids"
2573:Annu. Rev. Cell Dev. Biol
1821:Free University of Berlin
1573:had a 10% survival rate.
1133:cystathionine gamma-lyase
1116:through the intermediate
1098:cystathionine gamma-lyase
730:
723:
718:
663:1.5g/100g ethanol 19 °C
631:white crystals or powder
574:
546:
501:
155:
141:
131:
126:
88:
68:
6480:4-Maleylacetoacetic acid
6287:3-Hydroxyisobutyric acid
6143:Glutamate-1-semialdehyde
5657:Miscellaneous (E900–999)
4097:Dembrexine hydrochloride
3906:Cystinuria Clearinghouse
3662:10.15227/orgsyn.059.0190
3343:. CRC. pp. 71–102.
2984:Research in Microbiology
2878:Nat. Rev. Mol. Cell Biol
2253:– via kashrut.com.
1617:Cysteine is required by
1112:, which is converted to
822:proteinogenic amino acid
719:Supplementary data page
30:Not to be confused with
27:Proteinogenic amino acid
6326:2-Methylacetoacetyl-CoA
6282:3-Hydroxyisobutyryl-CoA
5818:metabolic intermediates
3080:Chemistry & Biology
2927:Microbiological Reviews
2529:10.3945/ajcn.110.003483
1985:10.1073/pnas.2110610118
1880:10.1351/pac198456050595
1816:Overview of Amino Acids
1709:In 1884 German chemist
986:)-Cysteine (left) and (
6595:Excitatory amino acids
6570:Glucogenic amino acids
6535:Cysteine sulfinic acid
6381:conversion to cysteine
6138:Formiminoglutamic acid
6065:3-Phosphoglyceric acid
5942:β-Methylglutaconyl-CoA
5114:Potassium permanganate
4770:neuromuscular blockade
4029:Hederae helicis folium
3572:Am J Health Syst Pharm
3539:10.1093/alcalc/agaa082
3527:Alcohol and Alcoholism
3468:URN:ISBN:952-10-3056-9
3456:University of Helsinki
3235:10.1002/anie.200300573
2412:10.1002/anie.198106681
2218:www.urmc.rochester.edu
1650:coordination complexes
1356:
1101:
991:
112:
98:
6267:α-Ketoisovaleric acid
5922:β-Ketoisocaproic acid
5917:α-Ketoisocaproic acid
4916:4-Dimethylaminophenol
3991:Antimony pentasulfide
2650:10.1093/jn/117.6.1003
2447:10.1007/s004250050112
2023:Biochemical Education
1903:on September 25, 2016
1493:yields meat flavors.
1477:Cysteine, mainly the
1388:endoplasmic reticulum
1382:; the cell transfers
1350:
1338:reducing environments
1327:Hydrophobicity scales
1265:, and nickel in the -
1255:alcohol dehydrogenase
1156:serine transacetylase
1091:
981:
820:) is a semiessential
460: (hydrochloride)
367:(glazing agents, ...)
183: (hydrochloride)
111:
97:
6354:-Adenosyl methionine
5937:β-Methylcrotonyl-CoA
5927:β-Ketoisocaproyl-CoA
5883:β-Hydroxybutyryl-CoA
5727:Potassium persulfate
5004:Paracetamol toxicity
4848:direct Xa inhibitors
4569:Alcohol intoxication
4182:Acetyldihydrocodeine
3912:Cysteine MS Spectrum
3755:Baumann, E. (1884).
2396:Offermanns, Heribert
1874:(5): 595–624, 1984,
1384:dehydroascorbic acid
1259:blue copper proteins
1231:iron-sulfur clusters
1166:Biological functions
1092:Cysteine synthesis:
1006:essential amino acid
725:Cysteine (data page)
102:Ball-and-stick model
55:Cys (disambiguation)
6527:Cysteine metabolism
6316:2-Methylbutyryl-CoA
6008:2-Aminomuconic acid
5988:3-Hydroxykynurenine
5733:Ammonium persulfate
4327:Bibenzonium bromide
3864:1999FEBSL.458...69N
3701:10.1021/ic00343a061
3689:Inorganic Chemistry
3615:Reprod. Fertil. Dev
3407:2019PLoSO..1414585O
2756:1999FEBSL.458...69N
2439:1997Plant.202..138H
1976:2021PNAS..11810610S
1970:(39): e2110610118.
1930:The Microbial World
1736:Cysteine metabolism
1448:complexes, such as
1121:-adenosylmethionine
648:Solubility in water
623: g·mol
116:Space-filling model
65:
6590:E-number additives
6575:Sulfur amino acids
6414:α-Ketobutyric acid
6391:α-Ketobutyric acid
6229:γ-Glutamylcysteine
5973:′-Formylkynurenine
5858:α-Aminoadipic acid
5618:acidity regulators
5548:Dehydroamino acids
5508:Encoded (proteins)
5444:Negative charge (p
5403:Positive charge (p
5190:Never to phase III
4987:Primary alcohols:
4945:Sodium thiosulfate
4829:Digoxin immune fab
4501:Never to phase III
4157:Cough suppressants
3922:2019-05-13 at the
3769:From pp. 301-302:
3584:10.2146/ajhp060050
3495:10.1007/BF01966822
3458:. pp. 41–44.
1827:2016-11-10 at the
1689:. You can help by
1637:of cysteine gives
1629:Chemical reactions
1469:encoded proteins.
1357:
1137:alpha-ketobutyrate
1102:
1080:‑cysteine.
1023:Industrial sources
992:
763:Infobox references
653:277g/L (at 25 °C)
566:: C((C(=O)))S
113:
99:
60:
6560:Alpha-Amino acids
6547:
6546:
6543:
6542:
6514:
6513:
6488:
6487:
6475:Homogentisic acid
6441:
6440:
6433:Methylmalonyl-CoA
6237:
6236:
6098:
6097:
6021:
6020:
5778:
5777:
5739:Potassium bromate
5720:
5711:
5651:Flavour enhancers
5645:anticaking agents
5557:
5556:
5518:Non-proteinogenic
5491:
5490:
5200:
5199:
5129:
5128:
4963:Calcium gluconate
4955:Hydrofluoric acid
4908:Cyanide poisoning
4885:Arsenic poisoning
4872:
4871:
4786:
4785:
4511:
4510:
4470:
4469:
4006:Guaiacolsulfonate
3986:Ammonium chloride
3695:(18): 3618–3620.
3650:Organic Syntheses
3627:10.1071/RD9940615
3350:978-0-203-90808-2
3282:10.1021/tx049856y
3276:(10): 1323–1328.
3229:(39): 4742–4758.
3035:10.1021/cr300163e
2617:978-0-935702-73-6
2490:10.1021/bi973101r
2394:Martens, Jürgen;
2380:978-3-527-30673-2
2247:MK News and Views
2107:10.1063/5.0012280
1751:Sullivan reaction
1707:
1706:
1491:Maillard reaction
1446:respiratory chain
1245:Metal ion binding
1229:. The sulfide in
1178:in proteins have
1160:cysteine synthase
866:
862:
858:
854:
771:Chemical compound
769:
768:
470:CompTox Dashboard
312:
224:Interactive image
213:Interactive image
122:
121:
82:
16:(Redirected from
6602:
6523:
6453:
6367:
6366:
6254:
6115:
6047:
6032:
5983:Anthranilic acid
5863:2-Oxoadipic acid
5835:
5805:
5798:
5791:
5782:
5769:Benzoyl peroxide
5757:Azodicarbonamide
5751:Chlorine dioxide
5718:
5709:
5681:Improving agents
5674:Synthetic glazes
5584:
5577:
5570:
5561:
5280:
5270:
5227:
5220:
5213:
5204:
5095:Potassium iodide
4921:Hydroxocobalamin
4881:
4821:Digoxin toxicity
4799:
4565:
4538:
4531:
4524:
4515:
4402:Levodropropizine
4261:Levopropoxyphene
4207:Dextromethorphan
4162:
4049:Potassium iodide
3953:
3946:
3939:
3930:
3893:
3875:
3834:
3768:
3752:
3746:
3745:
3711:
3705:
3704:
3672:
3666:
3665:
3645:
3639:
3638:
3610:
3604:
3603:
3567:
3561:
3560:
3550:
3521:
3515:
3514:
3478:
3472:
3471:
3445:
3439:
3438:
3428:
3418:
3386:
3380:
3379:
3377:
3376:
3361:
3355:
3354:
3334:
3328:
3327:
3319:402: S149–S150,
3308:
3302:
3301:
3261:
3255:
3254:
3214:
3208:
3207:
3167:
3161:
3160:
3142:
3118:
3112:
3111:
3071:
3065:
3064:
3054:
3029:(7): 4633–4679.
3023:Chemical Reviews
3014:
3008:
3007:
2975:
2969:
2968:
2958:
2918:
2912:
2911:
2893:
2869:
2863:
2862:
2860:
2859:
2844:
2838:
2837:
2835:
2834:
2825:. Archived from
2818:
2812:
2811:
2809:
2808:
2792:
2786:
2785:
2767:
2735:
2729:
2728:
2726:
2725:
2710:
2704:
2703:
2693:
2669:
2663:
2662:
2652:
2628:
2622:
2621:
2603:
2597:
2596:
2564:
2558:
2557:
2556:
2550:
2540:
2508:
2502:
2501:
2473:
2467:
2466:
2422:
2416:
2415:
2391:
2385:
2384:
2358:
2349:
2348:
2341:
2335:
2334:
2329:
2327:
2317:
2311:
2310:
2305:
2303:
2293:
2287:
2286:
2284:
2282:
2268:
2262:
2254:
2237:
2228:
2227:
2225:
2224:
2210:
2204:
2203:
2163:
2157:
2156:
2154:
2153:
2144:. Archived from
2134:
2128:
2127:
2109:
2085:
2076:
2075:
2073:
2072:
2063:. Archived from
2053:
2047:
2046:
2014:
2008:
2007:
1997:
1987:
1952:
1946:
1945:
1943:
1941:
1922:
1913:
1912:
1910:
1908:
1899:. Archived from
1889:
1883:
1882:
1868:Pure Appl. Chem.
1863:
1857:
1855:
1837:
1831:
1807:
1801:
1800:
1780:
1774:
1773:
1766:
1746:Saville reaction
1702:
1699:
1681:
1674:
1639:S-methylcysteine
1594:
1525:Michael addition
1496:
1480:
1306:sulfhydryl group
1257:, copper in the
1241:in the process.
1079:
1046:
1042:
1030:
1027:The majority of
950:
946:
942:
938:
931:
864:
860:
856:
852:
838:
819:
818:
815:
814:
811:
808:
805:
802:
799:
796:
793:
753:
747:
744:
743:
622:
610:
604:
601:
595:
589:
582:Chemical formula
494:
493:
478:
476:
459:
452:
432:
421:
407:
387:
361:
343:
335:
324:
310:
308:
300:
280:
260:
226:
215:
191: D-cysteine
190:
182:
175:
90:
80:
77:Skeletal formula
73:
66:
63:
21:
6610:
6609:
6605:
6604:
6603:
6601:
6600:
6599:
6550:
6549:
6548:
6539:
6510:
6484:
6437:
6418:
6399:
6364:
6363:
6330:
6296:
6277:Methacrylyl-CoA
6247:
6233:
6205:
6166:
6147:
6110:α-ketoglutarate
6108:
6094:
6085:Phosphocreatine
6054:
6040:
6017:
5951:
5887:
5820:
5809:
5779:
5774:
5705:
5688:Packaging gases
5664:
5593:
5588:
5558:
5553:
5552:
5533:Secondary amino
5487:
5450:
5439:
5409:
5398:
5364:
5331:
5271:
5262:
5236:
5231:
5201:
5196:
5195:
5180:Clinical trials
5159:
5153:Syrup of ipecac
5125:
5108:oxidizing agent
5076:
5028:
5007:(Acetaminophen)
5006:
4998:
4979:
4978:Ethylene glycol
4976:
4967:
4949:
4902:
4868:
4833:
4815:
4793:
4782:
4768:
4762:
4725:Opioid overdose
4719:
4671:
4670:Organophosphate
4668:
4659:
4636:
4618:
4611:
4593:
4586:
4559:
4552:
4542:
4512:
4507:
4506:
4491:Clinical trials
4466:
4362:Diphenhydramine
4300:
4175:and derivatives
4174:
4169:
4151:
4063:
4038:Syrup of ipecac
3967:
3957:
3924:Wayback Machine
3900:
3845:
3842:
3840:Further reading
3837:
3832:
3828:
3824:
3820:
3816:
3812:
3808:
3804:
3800:
3796:
3790:
3786:
3782:
3778:
3774:
3754:
3753:
3749:
3734:
3713:
3712:
3708:
3674:
3673:
3669:
3647:
3646:
3642:
3612:
3611:
3607:
3569:
3568:
3564:
3523:
3522:
3518:
3480:
3479:
3475:
3447:
3446:
3442:
3401:(3): e0214585.
3388:
3387:
3383:
3374:
3372:
3363:
3362:
3358:
3351:
3336:
3335:
3331:
3310:
3309:
3305:
3263:
3262:
3258:
3216:
3215:
3211:
3169:
3168:
3164:
3120:
3119:
3115:
3073:
3072:
3068:
3016:
3015:
3011:
2977:
2976:
2972:
2920:
2919:
2915:
2871:
2870:
2866:
2857:
2855:
2846:
2845:
2841:
2832:
2830:
2820:
2819:
2815:
2806:
2804:
2794:
2793:
2789:
2737:
2736:
2732:
2723:
2721:
2712:
2711:
2707:
2678:Eur. J. Biochem
2671:
2670:
2666:
2630:
2629:
2625:
2618:
2605:
2604:
2600:
2566:
2565:
2561:
2551:
2510:
2509:
2505:
2484:(25): 8965–72.
2475:
2474:
2470:
2424:
2423:
2419:
2393:
2392:
2388:
2381:
2360:
2359:
2352:
2343:
2342:
2338:
2325:
2323:
2319:
2318:
2314:
2301:
2299:
2295:
2294:
2290:
2280:
2278:
2270:
2269:
2265:
2251:Montreal Kosher
2240:
2238:
2231:
2222:
2220:
2212:
2211:
2207:
2165:
2164:
2160:
2151:
2149:
2136:
2135:
2131:
2087:
2086:
2079:
2070:
2068:
2055:
2054:
2050:
2016:
2015:
2011:
1954:
1953:
1949:
1939:
1937:
1924:
1923:
1916:
1906:
1904:
1891:
1890:
1886:
1865:
1864:
1860:
1852:
1839:
1838:
1834:
1829:Wayback Machine
1808:
1804:
1797:
1782:
1781:
1777:
1768:
1767:
1763:
1759:
1727:
1703:
1697:
1694:
1687:needs expansion
1672:
1666:
1658:
1631:
1615:
1592:
1585:
1583:-Acetylcysteine
1563:
1537:
1494:
1478:
1475:
1467:mitochondrially
1426:
1380:disulfide bonds
1334:disulfide bonds
1291:
1279:metallothionein
1263:cytochrome P450
1247:
1219:
1195:
1183:
1168:
1086:
1077:
1064:Alternatively,
1044:
1040:
1028:
1025:
997:
995:Dietary sources
948:
944:
940:
936:
929:
928:. Cysteine has
922:
847:reactions as a
836:
832:
828:
790:
786:
772:
765:
760:
759:
758: ?)
749:
745:
741:
737:
709:
703:
701:
696:Chiral rotation
677:
650:
620:
607:
598:
592:
584:
570:
567:
559:
554:
553:
542:
539:
538:
535:
529:
528:
525:
519:
518:
515:
509:
508:
497:
479:
472:
463:
435:
422:
410:
390:
377:
353:
316:
301: (Racemic)
283:
263:
229:
205:
194:
165:
151:
150:
137:
118:
104:
84:
74:
61:
58:
51:
28:
23:
22:
15:
12:
11:
5:
6608:
6606:
6598:
6597:
6592:
6587:
6585:Food additives
6582:
6577:
6572:
6567:
6562:
6552:
6551:
6545:
6544:
6541:
6540:
6538:
6537:
6531:
6529:
6520:
6516:
6515:
6512:
6511:
6509:
6508:
6499:
6497:
6490:
6489:
6486:
6485:
6483:
6482:
6477:
6472:
6466:
6464:
6450:
6443:
6442:
6439:
6438:
6436:
6435:
6429:
6427:
6420:
6419:
6417:
6416:
6410:
6408:
6401:
6400:
6398:
6397:
6388:
6376:
6375:
6370:
6356:
6341:
6339:
6332:
6331:
6329:
6328:
6323:
6318:
6313:
6307:
6305:
6298:
6297:
6295:
6294:
6289:
6284:
6279:
6274:
6272:Isobutyryl-CoA
6269:
6263:
6261:
6251:
6239:
6238:
6235:
6234:
6232:
6231:
6213:
6211:
6207:
6206:
6204:
6203:
6198:
6193:
6188:
6183:
6177:
6175:
6168:
6167:
6165:
6164:
6158:
6156:
6149:
6148:
6146:
6145:
6140:
6135:
6130:
6124:
6122:
6112:
6100:
6099:
6096:
6095:
6093:
6092:
6087:
6082:
6068:
6067:
6061:
6059:
6044:
6029:
6023:
6022:
6019:
6018:
6016:
6015:
6010:
6005:
6000:
5995:
5990:
5985:
5980:
5975:
5966:
5964:
5953:
5952:
5950:
5949:
5944:
5939:
5934:
5929:
5924:
5919:
5914:
5912:Isovaleryl-CoA
5909:
5904:
5898:
5896:
5889:
5888:
5886:
5885:
5880:
5875:
5873:Glutaconyl-CoA
5870:
5865:
5860:
5855:
5850:
5844:
5842:
5832:
5822:
5821:
5810:
5808:
5807:
5800:
5793:
5785:
5776:
5775:
5773:
5772:
5766:
5760:
5754:
5748:
5742:
5736:
5730:
5724:
5715:
5704:
5703:
5700:Foaming agents
5697:
5691:
5685:
5677:
5671:
5663:
5662:
5659:
5654:
5648:
5635:
5621:
5611:
5605:
5598:
5595:
5594:
5589:
5587:
5586:
5579:
5572:
5564:
5555:
5554:
5551:
5550:
5545:
5540:
5535:
5530:
5525:
5520:
5515:
5510:
5497:
5496:
5493:
5492:
5489:
5488:
5486:
5485:
5479:
5473:
5470:Selenocysteine
5467:
5461:
5454:
5452:
5448:
5441:
5440:
5438:
5437:
5432:
5426:
5420:
5413:
5411:
5407:
5400:
5399:
5397:
5396:
5391:
5386:
5381:
5375:
5373:
5366:
5365:
5363:
5362:
5357:
5352:
5347:
5341:
5339:
5333:
5332:
5330:
5329:
5324:
5319:
5314:
5309:
5303:
5298:
5288:
5286:
5277:
5273:
5272:
5265:
5263:
5261:
5260:
5255:
5250:
5244:
5242:
5241:General topics
5238:
5237:
5232:
5230:
5229:
5222:
5215:
5207:
5198:
5197:
5194:
5193:
5192:
5191:
5188:
5177:
5171:
5165:
5164:
5161:
5160:
5158:
5157:
5156:
5155:
5145:
5143:Copper sulfate
5139:
5137:
5131:
5130:
5127:
5126:
5124:
5123:
5118:
5117:
5116:
5104:
5099:
5098:
5097:
5084:
5082:
5078:
5077:
5075:
5070:
5065:
5060:
5058:
5057:
5056:
5050:
5045:
5030:
5029:
5027:
5026:
5021:
5016:
5014:Acetylcysteine
5010:
5008:
5000:
4999:
4997:
4996:
4991:
4984:
4982:
4969:
4968:
4966:
4965:
4959:
4957:
4951:
4950:
4948:
4947:
4942:
4941:
4940:
4938:Sodium nitrite
4935:
4923:
4918:
4912:
4910:
4904:
4903:
4901:
4900:
4895:
4889:
4887:
4878:
4874:
4873:
4870:
4869:
4867:
4866:
4855:
4852:Andexanet alfa
4843:
4841:
4839:Anticoagulants
4835:
4834:
4832:
4831:
4825:
4823:
4817:
4816:
4814:
4813:
4807:
4805:
4796:
4788:
4787:
4784:
4783:
4781:
4780:
4774:
4772:
4764:
4763:
4761:
4760:
4755:
4750:
4745:
4740:
4735:
4729:
4727:
4721:
4720:
4718:
4717:
4715:Cholinesterase
4709:
4708:
4707:
4702:
4692:
4687:
4682:
4676:
4674:
4661:
4660:
4658:
4657:
4652:
4646:
4644:
4638:
4637:
4635:
4634:
4629:
4623:
4621:
4617:Benzodiazepine
4613:
4612:
4610:
4609:
4604:
4598:
4596:
4588:
4587:
4585:
4584:
4579:
4573:
4571:
4562:
4554:
4553:
4543:
4541:
4540:
4533:
4526:
4518:
4509:
4508:
4505:
4504:
4503:
4502:
4499:
4488:
4482:
4476:
4475:
4472:
4471:
4468:
4467:
4465:
4464:
4459:
4454:
4449:
4444:
4439:
4434:
4429:
4424:
4419:
4414:
4409:
4404:
4399:
4394:
4389:
4384:
4379:
4374:
4369:
4364:
4359:
4354:
4349:
4344:
4339:
4334:
4329:
4324:
4319:
4314:
4308:
4306:
4302:
4301:
4299:
4298:
4293:
4288:
4283:
4278:
4273:
4268:
4263:
4258:
4253:
4248:
4243:
4229:
4224:
4219:
4214:
4212:Dihydrocodeine
4209:
4204:
4194:
4189:
4187:Benzylmorphine
4184:
4178:
4176:
4159:
4153:
4152:
4150:
4149:
4144:
4139:
4134:
4129:
4124:
4119:
4114:
4109:
4104:
4099:
4094:
4089:
4084:
4079:
4077:Acetylcysteine
4073:
4071:
4065:
4064:
4062:
4061:
4056:
4051:
4046:
4041:
4031:
4026:
4008:
4003:
3998:
3993:
3988:
3983:
3977:
3975:
3969:
3968:
3958:
3956:
3955:
3948:
3941:
3933:
3927:
3926:
3914:
3909:
3903:Holly (2005).
3899:
3898:External links
3896:
3895:
3894:
3841:
3838:
3836:
3835:
3830:
3826:
3822:
3818:
3814:
3810:
3806:
3802:
3798:
3794:
3788:
3784:
3780:
3776:
3772:
3747:
3732:
3706:
3667:
3640:
3605:
3578:(19): 1821–7.
3562:
3533:(6): 660–666.
3516:
3483:Agents Actions
3473:
3440:
3381:
3356:
3349:
3329:
3303:
3256:
3209:
3162:
3113:
3086:(8): 677–693.
3066:
3009:
2990:(7): 481–486.
2970:
2933:(1): 229–264.
2913:
2891:10.1038/nrm954
2884:(11): 836–47.
2864:
2839:
2813:
2787:
2730:
2705:
2664:
2643:(6): 1003–10.
2623:
2616:
2598:
2559:
2523:(3): 847–853.
2503:
2468:
2417:
2386:
2379:
2350:
2336:
2312:
2288:
2263:
2229:
2205:
2178:(4): 922–926.
2158:
2129:
2077:
2048:
2029:(2): 116–118.
2009:
1947:
1936:on 25 May 2013
1914:
1884:
1858:
1850:
1832:
1802:
1795:
1786:Food Chemistry
1775:
1770:"PubChem data"
1760:
1758:
1755:
1754:
1753:
1748:
1743:
1738:
1733:
1726:
1723:
1705:
1704:
1684:
1682:
1668:Main article:
1665:
1662:
1657:
1654:
1630:
1627:
1614:
1611:
1584:
1578:
1561:
1536:
1533:
1506:permanent-wave
1499:processing aid
1474:
1471:
1462:thiyl radicals
1425:
1422:
1290:
1287:
1246:
1243:
1218:
1215:
1194:
1191:
1181:
1167:
1164:
1154:by the enzyme
1085:
1082:
1024:
1021:
1019:is available.
996:
993:
973:selenocysteine
921:
918:
875:, "bladder".
770:
767:
766:
761:
739:
738:
734:standard state
731:
728:
727:
721:
720:
716:
715:
707:
704:
699:
694:
691:
690:
683:conjugate acid
679:
675:
665:
664:
661:
655:
654:
651:
646:
643:
642:
639:
633:
632:
629:
625:
624:
618:
612:
611:
605:
596:
590:
585:
580:
577:
576:
572:
571:
569:
568:
562:
560:
557:
549:
548:
547:
544:
543:
541:
540:
536:
533:
532:
530:
526:
523:
522:
520:
516:
513:
512:
504:
503:
502:
499:
498:
496:
495:
482:
480:
468:
465:
464:
462:
461:
453:
445:
443:
437:
436:
434:
433:
425:
423:
415:
412:
411:
409:
408:
400:
398:
392:
391:
389:
388:
380:
378:
373:
370:
369:
363:
355:
354:
352:
351:
347:
345:
337:
336:
326:
318:
317:
315:
314:
302:
293:
291:
285:
284:
282:
281:
273:
271:
265:
264:
262:
261:
253:
251:
245:
244:
235:
234:Abbreviations
231:
230:
228:
227:
216:
208:
206:
199:
196:
195:
193:
192:
184:
176:
168:
166:
161:
158:
157:
153:
152:
149:
148:
144:
143:
139:
138:
135:
129:
128:
124:
123:
120:
119:
114:
105:
100:
86:
85:
75:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
6607:
6596:
6593:
6591:
6588:
6586:
6583:
6581:
6578:
6576:
6573:
6571:
6568:
6566:
6563:
6561:
6558:
6557:
6555:
6536:
6533:
6532:
6530:
6528:
6524:
6521:
6517:
6507:
6506:
6501:
6500:
6498:
6496:
6491:
6481:
6478:
6476:
6473:
6471:
6468:
6467:
6465:
6462:
6458:
6457:phenylalanine
6454:
6451:
6449:
6444:
6434:
6431:
6430:
6428:
6425:
6424:propionyl-CoA
6421:
6415:
6412:
6411:
6409:
6406:
6402:
6396:
6392:
6389:
6387:
6386:Cystathionine
6384:
6382:
6378:
6377:
6374:
6371:
6369:
6368:-homocysteine
6361:
6357:
6355:
6353:
6349:
6347:
6343:
6342:
6340:
6337:
6333:
6327:
6324:
6322:
6319:
6317:
6314:
6312:
6309:
6308:
6306:
6303:
6299:
6293:
6290:
6288:
6285:
6283:
6280:
6278:
6275:
6273:
6270:
6268:
6265:
6264:
6262:
6259:
6255:
6252:
6250:
6245:
6244:propionyl-CoA
6240:
6230:
6226:
6222:
6218:
6215:
6214:
6212:
6208:
6202:
6199:
6197:
6194:
6192:
6189:
6187:
6184:
6182:
6179:
6178:
6176:
6173:
6169:
6163:
6160:
6159:
6157:
6154:
6150:
6144:
6141:
6139:
6136:
6134:
6131:
6129:
6128:Urocanic acid
6126:
6125:
6123:
6120:
6116:
6113:
6111:
6106:
6101:
6091:
6088:
6086:
6083:
6081:
6077:
6073:
6070:
6069:
6066:
6063:
6062:
6060:
6057:
6052:
6048:
6045:
6043:
6038:
6033:
6030:
6028:
6024:
6014:
6011:
6009:
6006:
6004:
6001:
5999:
5996:
5994:
5991:
5989:
5986:
5984:
5981:
5979:
5976:
5974:
5972:
5968:
5967:
5965:
5962:
5958:
5954:
5948:
5945:
5943:
5940:
5938:
5935:
5933:
5930:
5928:
5925:
5923:
5920:
5918:
5915:
5913:
5910:
5908:
5905:
5903:
5900:
5899:
5897:
5894:
5890:
5884:
5881:
5879:
5876:
5874:
5871:
5869:
5866:
5864:
5861:
5859:
5856:
5854:
5851:
5849:
5846:
5845:
5843:
5840:
5836:
5833:
5831:
5827:
5823:
5819:
5816:
5813:
5806:
5801:
5799:
5794:
5792:
5787:
5786:
5783:
5770:
5767:
5764:
5761:
5758:
5755:
5752:
5749:
5746:
5743:
5740:
5737:
5734:
5731:
5728:
5725:
5722:
5716:
5713:
5707:
5706:
5701:
5698:
5695:
5692:
5689:
5686:
5684:
5682:
5678:
5675:
5672:
5669:
5666:
5665:
5660:
5658:
5655:
5652:
5649:
5646:
5642:
5639:
5636:
5633:
5629:
5625:
5622:
5619:
5615:
5612:
5609:
5608:Preservatives
5606:
5603:
5600:
5599:
5596:
5592:
5585:
5580:
5578:
5573:
5571:
5566:
5565:
5562:
5549:
5546:
5544:
5543:D-amino acids
5541:
5539:
5536:
5534:
5531:
5529:
5526:
5524:
5521:
5519:
5516:
5514:
5511:
5509:
5505:
5503:
5499:
5498:
5494:
5483:
5480:
5477:
5474:
5471:
5468:
5465:
5464:Glutamic acid
5462:
5459:
5458:Aspartic acid
5456:
5455:
5453:
5447:
5442:
5436:
5433:
5430:
5427:
5424:
5421:
5418:
5415:
5414:
5412:
5406:
5401:
5395:
5392:
5390:
5387:
5385:
5382:
5380:
5377:
5376:
5374:
5371:
5367:
5361:
5360:Phenylalanine
5358:
5356:
5353:
5351:
5348:
5346:
5343:
5342:
5340:
5338:
5334:
5328:
5325:
5323:
5320:
5318:
5315:
5313:
5310:
5307:
5304:
5302:
5299:
5297:
5293:
5290:
5289:
5287:
5285:
5281:
5278:
5276:By properties
5274:
5269:
5259:
5256:
5254:
5251:
5249:
5246:
5245:
5243:
5239:
5235:
5228:
5223:
5221:
5216:
5214:
5209:
5208:
5205:
5189:
5187:
5184:
5183:
5181:
5178:
5175:
5172:
5170:
5167:
5166:
5162:
5154:
5151:
5150:
5149:
5146:
5144:
5141:
5140:
5138:
5136:
5132:
5122:
5119:
5115:
5112:
5111:
5110:
5109:
5105:
5103:
5100:
5096:
5093:
5092:
5091:
5090:
5086:
5085:
5083:
5079:
5074:
5073:Prussian blue
5071:
5069:
5066:
5064:
5061:
5059:
5054:
5051:
5049:
5046:
5044:
5041:
5040:
5039:
5035:
5031:
5025:
5022:
5020:
5017:
5015:
5012:
5011:
5009:
5005:
5001:
4995:
4992:
4990:
4986:
4985:
4983:
4981:
4974:
4970:
4964:
4961:
4960:
4958:
4956:
4952:
4946:
4943:
4939:
4936:
4934:
4931:
4930:
4929:
4928:
4924:
4922:
4919:
4917:
4914:
4913:
4911:
4909:
4905:
4899:
4896:
4894:
4891:
4890:
4888:
4886:
4882:
4879:
4875:
4864:
4860:
4856:
4853:
4849:
4845:
4844:
4842:
4840:
4836:
4830:
4827:
4826:
4824:
4822:
4818:
4812:
4809:
4808:
4806:
4804:
4800:
4797:
4795:
4789:
4779:
4776:
4775:
4773:
4771:
4765:
4759:
4756:
4754:
4751:
4749:
4746:
4744:
4741:
4739:
4736:
4734:
4733:Diprenorphine
4731:
4730:
4728:
4726:
4722:
4716:
4713:
4710:
4706:
4703:
4701:
4698:
4697:
4696:
4693:
4691:
4688:
4686:
4683:
4681:
4678:
4677:
4675:
4673:
4666:
4662:
4656:
4653:
4651:
4650:Physostigmine
4648:
4647:
4645:
4643:
4639:
4633:
4630:
4628:
4625:
4624:
4622:
4620:
4614:
4608:
4605:
4603:
4600:
4599:
4597:
4595:
4589:
4583:
4580:
4578:
4575:
4574:
4572:
4570:
4566:
4563:
4561:
4555:
4550:
4546:
4539:
4534:
4532:
4527:
4525:
4520:
4519:
4516:
4500:
4498:
4495:
4494:
4492:
4489:
4486:
4483:
4481:
4478:
4477:
4473:
4463:
4460:
4458:
4455:
4453:
4452:Prenoxdiazine
4450:
4448:
4445:
4443:
4440:
4438:
4437:Pentoxyverine
4435:
4433:
4430:
4428:
4425:
4423:
4420:
4418:
4415:
4413:
4410:
4408:
4405:
4403:
4400:
4398:
4395:
4393:
4390:
4388:
4385:
4383:
4380:
4378:
4375:
4373:
4370:
4368:
4365:
4363:
4360:
4358:
4357:Dimethoxanate
4355:
4353:
4350:
4348:
4345:
4343:
4340:
4338:
4335:
4333:
4330:
4328:
4325:
4323:
4320:
4318:
4315:
4313:
4310:
4309:
4307:
4303:
4297:
4294:
4292:
4289:
4287:
4284:
4282:
4279:
4277:
4276:Nicodicodeine
4274:
4272:
4269:
4267:
4264:
4262:
4259:
4257:
4256:Levomethadone
4254:
4252:
4249:
4247:
4246:Hydromorphone
4244:
4241:
4237:
4233:
4230:
4228:
4225:
4223:
4222:Ethylmorphine
4220:
4218:
4215:
4213:
4210:
4208:
4205:
4202:
4198:
4195:
4193:
4190:
4188:
4185:
4183:
4180:
4179:
4177:
4172:
4167:
4163:
4160:
4158:
4154:
4148:
4145:
4143:
4140:
4138:
4135:
4133:
4130:
4128:
4125:
4123:
4120:
4118:
4115:
4113:
4110:
4108:
4105:
4103:
4100:
4098:
4095:
4093:
4092:Carbocisteine
4090:
4088:
4085:
4083:
4080:
4078:
4075:
4074:
4072:
4070:
4066:
4060:
4057:
4055:
4052:
4050:
4047:
4045:
4044:Levoverbenone
4042:
4039:
4035:
4032:
4030:
4027:
4024:
4020:
4016:
4012:
4009:
4007:
4004:
4002:
3999:
3997:
3994:
3992:
3989:
3987:
3984:
3982:
3979:
3978:
3976:
3974:
3970:
3965:
3961:
3954:
3949:
3947:
3942:
3940:
3935:
3934:
3931:
3925:
3921:
3918:
3915:
3913:
3910:
3908:
3907:
3902:
3901:
3897:
3891:
3887:
3883:
3879:
3874:
3869:
3865:
3861:
3857:
3853:
3849:
3844:
3843:
3839:
3792:
3766:
3763:(in German).
3762:
3758:
3751:
3748:
3743:
3739:
3735:
3733:9780121820435
3729:
3725:
3721:
3717:
3710:
3707:
3702:
3698:
3694:
3690:
3686:
3683:)- and Tris((
3682:
3679:)-Cysteinato-
3678:
3671:
3668:
3663:
3659:
3655:
3651:
3644:
3641:
3636:
3632:
3628:
3624:
3621:(5): 615–23.
3620:
3616:
3609:
3606:
3601:
3597:
3593:
3589:
3585:
3581:
3577:
3573:
3566:
3563:
3558:
3554:
3549:
3544:
3540:
3536:
3532:
3528:
3520:
3517:
3512:
3508:
3504:
3500:
3496:
3492:
3489:(2): 125–30.
3488:
3484:
3477:
3474:
3469:
3465:
3461:
3457:
3453:
3452:
3444:
3441:
3436:
3432:
3427:
3422:
3417:
3412:
3408:
3404:
3400:
3396:
3392:
3385:
3382:
3371:on 2009-05-12
3370:
3366:
3360:
3357:
3352:
3346:
3342:
3341:
3333:
3330:
3326:
3322:
3318:
3314:
3307:
3304:
3299:
3295:
3291:
3287:
3283:
3279:
3275:
3271:
3267:
3260:
3257:
3252:
3248:
3244:
3240:
3236:
3232:
3228:
3224:
3220:
3213:
3210:
3205:
3201:
3197:
3193:
3189:
3185:
3181:
3177:
3173:
3166:
3163:
3158:
3154:
3150:
3146:
3141:
3136:
3132:
3128:
3124:
3117:
3114:
3109:
3105:
3101:
3097:
3093:
3089:
3085:
3081:
3077:
3070:
3067:
3062:
3058:
3053:
3048:
3044:
3040:
3036:
3032:
3028:
3024:
3020:
3013:
3010:
3005:
3001:
2997:
2993:
2989:
2985:
2981:
2974:
2971:
2966:
2962:
2957:
2952:
2948:
2944:
2940:
2936:
2932:
2928:
2924:
2917:
2914:
2909:
2905:
2901:
2897:
2892:
2887:
2883:
2879:
2875:
2868:
2865:
2854:on 2012-10-02
2853:
2849:
2843:
2840:
2829:on 2012-09-05
2828:
2824:
2817:
2814:
2802:
2798:
2791:
2788:
2783:
2779:
2775:
2771:
2766:
2761:
2757:
2753:
2749:
2745:
2741:
2734:
2731:
2720:on 2015-09-07
2719:
2715:
2709:
2706:
2701:
2697:
2692:
2687:
2684:(3): 346–50.
2683:
2679:
2675:
2668:
2665:
2660:
2656:
2651:
2646:
2642:
2638:
2634:
2627:
2624:
2619:
2613:
2609:
2602:
2599:
2594:
2590:
2586:
2582:
2578:
2574:
2570:
2563:
2560:
2555:
2548:
2544:
2539:
2534:
2530:
2526:
2522:
2518:
2514:
2507:
2504:
2499:
2495:
2491:
2487:
2483:
2479:
2472:
2469:
2464:
2460:
2456:
2452:
2448:
2444:
2440:
2436:
2433:(2): 138–48.
2432:
2428:
2421:
2418:
2413:
2409:
2405:
2401:
2397:
2390:
2387:
2382:
2376:
2372:
2368:
2364:
2357:
2355:
2351:
2346:
2340:
2337:
2333:
2322:
2316:
2313:
2309:
2298:
2292:
2289:
2277:
2273:
2267:
2264:
2260:
2259:
2252:
2248:
2244:
2236:
2234:
2230:
2219:
2215:
2209:
2206:
2201:
2197:
2193:
2189:
2185:
2181:
2177:
2173:
2169:
2162:
2159:
2148:on 2022-05-22
2147:
2143:
2139:
2133:
2130:
2125:
2121:
2117:
2113:
2108:
2103:
2100:(3): 035103.
2099:
2095:
2091:
2084:
2082:
2078:
2067:on 2022-05-22
2066:
2062:
2058:
2052:
2049:
2044:
2040:
2036:
2032:
2028:
2024:
2020:
2013:
2010:
2005:
2001:
1996:
1991:
1986:
1981:
1977:
1973:
1969:
1965:
1964:
1959:
1951:
1948:
1935:
1931:
1927:
1921:
1919:
1915:
1902:
1898:
1894:
1888:
1885:
1881:
1877:
1873:
1869:
1862:
1859:
1853:
1851:0-8493-0462-8
1847:
1843:
1836:
1833:
1830:
1826:
1822:
1818:
1817:
1812:
1806:
1803:
1798:
1796:9783540699330
1792:
1788:
1787:
1779:
1776:
1771:
1765:
1762:
1756:
1752:
1749:
1747:
1744:
1742:
1739:
1737:
1734:
1732:
1729:
1728:
1724:
1722:
1720:
1716:
1712:
1711:Eugen Baumann
1701:
1692:
1688:
1685:This section
1683:
1680:
1676:
1675:
1671:
1663:
1661:
1655:
1653:
1651:
1647:
1644:
1640:
1636:
1628:
1626:
1624:
1620:
1612:
1610:
1608:
1607:acetaminophen
1604:
1600:
1596:
1590:
1582:
1579:
1577:
1574:
1572:
1571:control group
1568:
1564:
1557:
1552:
1550:
1546:
1542:
1534:
1532:
1530:
1526:
1522:
1517:
1515:
1511:
1507:
1502:
1500:
1492:
1488:
1484:
1472:
1470:
1468:
1463:
1459:
1455:
1451:
1447:
1443:
1439:
1435:
1431:
1423:
1421:
1419:
1415:
1411:
1408:
1404:
1400:
1396:
1391:
1389:
1385:
1381:
1377:
1373:
1371:
1367:
1366:sulfonic acid
1363:
1362:sulfinic acid
1354:
1349:
1345:
1343:
1339:
1335:
1330:
1328:
1324:
1320:
1316:
1311:
1307:
1303:
1298:
1296:
1288:
1286:
1284:
1280:
1276:
1272:
1268:
1264:
1260:
1256:
1252:
1244:
1242:
1240:
1236:
1232:
1228:
1224:
1216:
1214:
1212:
1211:glutamic acid
1208:
1204:
1200:
1192:
1190:
1188:
1184:
1177:
1173:
1165:
1163:
1161:
1158:. The enzyme
1157:
1153:
1152:-acetylserine
1151:
1146:
1142:
1138:
1134:
1131:. The enzyme
1130:
1129:cystathionine
1126:
1122:
1120:
1115:
1111:
1107:
1099:
1095:
1090:
1083:
1081:
1075:
1071:
1067:
1062:
1060:
1059:
1054:
1050:
1037:
1034:
1022:
1020:
1018:
1014:
1011:
1010:malabsorption
1007:
1002:
994:
989:
985:
980:
976:
974:
970:
966:
962:
958:
954:
935:in the older
934:
927:
919:
917:
916:UGU and UGC.
915:
911:
906:
904:
899:
897:
893:
889:
885:
881:
876:
874:
870:
850:
846:
842:
827:
823:
817:
784:
780:
776:
764:
757:
752:
735:
729:
726:
722:
717:
713:
705:
697:
693:
692:
688:
684:
680:
674:
670:
667:
666:
662:
660:
657:
656:
652:
649:
645:
644:
640:
638:
637:Melting point
635:
634:
630:
627:
626:
619:
617:
614:
613:
586:
583:
579:
578:
573:
565:
561:
558:C((C(=O)O)N)S
556:
552:
545:
531:
521:
511:
507:
500:
492:
488:
487:DTXSID8022876
484:
483:
481:
471:
467:
466:
458:
454:
451:
447:
446:
444:
442:
439:
438:
431:
427:
426:
424:
418:
414:
413:
406:
402:
401:
399:
397:
394:
393:
386:
382:
381:
379:
376:
372:
371:
368:
364:
362:
357:
356:
349:
348:
346:
344:
339:
338:
334:
330:
327:
325:
323:ECHA InfoCard
320:
319:
307:
303:
299:
295:
294:
292:
290:
287:
286:
279:
275:
274:
272:
270:
267:
266:
259:
255:
254:
252:
250:
247:
246:
243:
239:
236:
233:
232:
225:
220:
217:
214:
210:
209:
207:
203:
198:
197:
189:
185:
181:
177:
174:
170:
169:
167:
164:
160:
159:
154:
146:
145:
140:
134:
130:
125:
117:
110:
106:
103:
96:
92:
91:
87:
78:
72:
67:
56:
49:
45:
41:
37:
33:
19:
6502:
6495:oxaloacetate
6394:
6379:
6373:Homocysteine
6359:
6351:
6344:
6249:succinyl-CoA
6216:
6080:Glycocyamine
6013:Glutaryl-CoA
5970:
5878:Crotonyl-CoA
5868:Glutaryl-CoA
5848:Saccharopine
5708:
5679:
5656:
5614:Antioxidants
5500:
5475:
5445:
5404:
5258:Genetic code
5106:
5087:
5034:Toxic metals
4933:Amyl nitrite
4925:
4803:Beta blocker
4711:
4642:GHB overdose
4372:Droxypropine
4367:Dropropizine
4347:Cloperastine
4317:Benproperine
4281:Normethadone
4240:+homatropine
4236:+guaifenesin
4201:+guaifenesin
4107:Dornase alfa
4023:+oxomemazine
4019:+hydrocodone
3973:Expectorants
3904:
3858:(1): 69–71.
3855:
3851:
3770:
3764:
3760:
3750:
3715:
3709:
3692:
3688:
3684:
3680:
3676:
3670:
3653:
3649:
3643:
3618:
3614:
3608:
3575:
3571:
3565:
3548:10138/339340
3530:
3526:
3519:
3486:
3482:
3476:
3450:
3443:
3398:
3394:
3384:
3373:. Retrieved
3369:the original
3359:
3339:
3332:
3316:
3312:
3306:
3273:
3269:
3259:
3226:
3222:
3212:
3182:(1): 37–44.
3179:
3175:
3165:
3133:(1): 32–46.
3130:
3126:
3116:
3083:
3079:
3069:
3026:
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2987:
2983:
2973:
2930:
2926:
2916:
2881:
2877:
2867:
2856:. Retrieved
2852:the original
2842:
2831:. Retrieved
2827:the original
2816:
2805:. Retrieved
2800:
2790:
2750:(1): 69–71.
2747:
2743:
2733:
2722:. Retrieved
2718:the original
2708:
2681:
2677:
2667:
2640:
2636:
2626:
2607:
2601:
2576:
2572:
2562:
2520:
2516:
2506:
2481:
2478:Biochemistry
2477:
2471:
2430:
2426:
2420:
2403:
2399:
2389:
2362:
2339:
2331:
2324:. Retrieved
2315:
2307:
2300:. Retrieved
2291:
2279:. Retrieved
2275:
2266:
2256:
2246:
2221:. Retrieved
2217:
2208:
2175:
2171:
2161:
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2146:the original
2141:
2132:
2097:
2093:
2069:. Retrieved
2065:the original
2060:
2051:
2026:
2022:
2012:
1967:
1961:
1950:
1940:16 September
1938:. Retrieved
1934:the original
1929:
1905:. Retrieved
1901:the original
1896:
1887:
1871:
1867:
1861:
1841:
1835:
1814:
1805:
1789:. Springer.
1785:
1778:
1764:
1708:
1698:January 2023
1695:
1691:adding to it
1686:
1659:
1643:thiazolidine
1632:
1616:
1605:in cases of
1599:acetyl group
1588:
1586:
1580:
1575:
1553:
1545:acetaldehyde
1538:
1518:
1503:
1501:for baking.
1476:
1473:Applications
1430:genetic code
1427:
1399:nucleophilic
1392:
1374:
1358:
1331:
1299:
1292:
1275:heavy metals
1267:hydrogenases
1251:zinc fingers
1248:
1220:
1196:
1172:nucleophilic
1169:
1149:
1118:
1114:homocysteine
1103:
1084:Biosynthesis
1073:
1063:
1058:E. coli
1056:
1038:
1026:
998:
987:
983:
964:
960:
956:
952:
923:
908:Cysteine is
907:
900:
895:
891:
877:
872:
782:
778:
774:
773:
711:
672:
241:
237:
156:Identifiers
142:Other names
6225:glutathione
5632:emulsifiers
5628:stabilisers
5538:Imino acids
5502:Amino acids
5435:Pyrrolysine
5372:, uncharged
5176:from market
5148:Ipecacuanha
5063:Dimercaprol
5019:Glutathione
4893:Dimercaprol
4792:Circulatory
4767:Reversal of
4705:Pralidoxime
4665:Nerve agent
4627:Cyprodenate
4592:Barbiturate
4487:from market
4447:Piperidione
4412:Moguisteine
4322:Benzonatate
4312:Alloclamide
4271:Nicocodeine
4232:Hydrocodone
4192:Butorphanol
4137:Neltenexine
4034:Ipecacuanha
4011:Guaifenesin
3981:Althea root
3464:10138/22689
2239:See, e.g.,
2142:ambermd.org
2061:ambermd.org
1731:Amino acids
1646:thioproline
1635:Methylation
1549:thioproline
1450:Complexes I
1403:prenylation
1302:hydrophilic
1235:nitrogenase
1203:glutathione
1199:antioxidant
1070:thiazolines
1051:and Muslim
882:derivative
849:nucleophile
829:HOOC−CH(−NH
628:Appearance
575:Properties
329:100.000.145
278:ChEMBL54943
258:CHEBI:15356
6554:Categories
6505:urea cycle
6362:-Adenosyl-
6336:methionine
6321:Tiglyl-CoA
6302:isoleucine
6201:Putrescine
6196:Cadaverine
6191:Citrulline
6090:Creatinine
5978:Kynurenine
5957:tryptophan
5830:acetyl-CoA
5815:metabolism
5812:Amino acid
5702:(E990–999)
5696:(E950–969)
5694:Sweeteners
5690:(E930–949)
5683:(E920–929)
5676:(E910–919)
5670:(E900–909)
5653:(E600–699)
5647:(E500–599)
5641:regulators
5634:(E400–499)
5624:Thickeners
5620:(E300–399)
5610:(E200–299)
5604:(E100–199)
5528:Glucogenic
5379:Asparagine
5355:Tryptophan
5312:Methionine
5301:Isoleucine
5089:iodine-131
5024:Methionine
4994:Fomepizole
4778:Sugammadex
4758:Naltrexone
4748:Nalorphine
4632:Flumazenil
4577:Metadoxine
4457:Tipepidine
4442:Pipazetate
4422:Nepinalone
4417:Morclofone
4407:Meprotixol
4397:Isoaminile
4387:Gefapixant
4342:Clofedanol
4337:Clobutinol
4332:Butamirate
4291:Pholcodine
4217:Dimemorfan
4168:alkaloids,
4122:Letosteine
4117:Erdosteine
4112:Eprazinone
4087:Bromhexine
4069:Mucolytics
3833:(SH)COOH .
3767:: 299–305.
3525:Anxiety".
3375:2009-09-06
3127:Aging Cell
2858:2012-09-16
2833:2012-09-16
2807:2012-09-16
2724:2015-09-09
2579:: 457–86.
2406:(8): 668.
2223:2024-05-13
2152:2022-06-02
2071:2022-06-02
1757:References
1741:Cystinuria
1623:transgenic
1609:overdose.
1521:Maleimides
1483:enantiomer
1442:tryptophan
1434:methionine
1351:Figure 2:
1315:methionine
1261:, iron in
1227:metabolism
1110:methionine
1033:hydrolysis
1017:methionine
926:zwitterion
659:Solubility
616:Molar mass
564:Zwitterion
457:A9U1687S1S
450:K848JZ4886
375:IUPHAR/BPS
289:ChemSpider
219:Zwitterion
200:3D model (
163:CAS Number
133:IUPAC name
64:-Cysteine
6405:threonine
6221:glutamate
6186:Ornithine
6119:histidine
6105:glutamate
5932:β-Leucine
5763:Carbamide
5712:-cysteine
5591:E numbers
5523:Ketogenic
5513:Essential
5429:Histidine
5394:Threonine
5384:Glutamine
5345:Histidine
5284:Aliphatic
5186:Phase III
5174:Withdrawn
4980:poisoning
4863:Protamine
4743:Nalmefene
4712:see also:
4700:Obidoxime
4685:Biperiden
4672:poisoning
4655:SCH-50911
4607:Ethamivan
4602:Bemegride
4545:Antidotes
4497:Phase III
4485:Withdrawn
4432:Oxolamine
4382:Fominoben
4377:Fedrilate
4286:Noscapine
4266:Methadone
4147:Stepronin
4059:Tyloxapol
3852:FEBS Lett
3290:0893-228X
3243:1433-7851
3196:0891-5849
3149:1474-9718
3100:1074-5521
3043:0009-2665
2947:0146-0749
2744:FEBS Lett
2281:26 August
2124:220796795
2043:0307-4412
1595:-cysteine
1487:precursor
1407:Ubiquitin
1323:threonine
1225:in human
1061:strain.
1013:syndromes
933:chirality
920:Structure
898:as well.
880:disulfide
845:enzymatic
824:with the
689:), 10.78
685:), 8.33 (
350:200-158-2
342:EC Number
83:-cysteine
18:Cysteinyl
6461:tyrosine
6448:fumarate
6395:Cysteine
6217:cysteine
6181:Agmatine
6172:arginine
6076:creatine
6037:pyruvate
5853:Allysine
5745:Chlorine
5721:-cystine
5482:Tyrosine
5476:Cysteine
5423:Arginine
5350:Tyrosine
5337:Aromatic
5068:Edetates
5053:thallium
4973:Methanol
4898:Succimer
4857:against
4846:against
4811:Glucagon
4753:Naloxone
4738:Doxapram
4690:Diazepam
4680:Atropine
4619:overdose
4594:overdose
4582:Thiamine
4462:Zipeprol
4427:Oxeladin
4392:Glaucine
4352:Dibunate
4296:Thebacon
4251:Laudanum
4142:Sobrerol
4127:Mannitol
4102:Domiodol
4082:Ambroxol
4015:+codeine
4001:Creosote
3920:Archived
3890:34980474
3882:10518936
3592:16990628
3557:32808029
3435:30925182
3395:PLOS ONE
3298:15487892
3251:14562341
3204:12086680
3157:18028257
3108:12954327
3061:23514336
3004:19524038
2900:12415301
2782:34980474
2774:10518936
2593:16824008
2547:21795440
2326:July 28,
2200:14895681
2192:25669310
2116:32716185
2004:34556581
1907:15 April
1825:Archived
1811:Cysteine
1725:See also
1603:antidote
1591:-Acetyl-
1567:thiamine
1541:hangover
1438:tyrosine
1414:caspases
1319:tyrosine
1310:hydroxyl
1308:and the
1271:affinity
1187:thiolate
1176:residues
1145:bacteria
969:selenium
903:E number
888:proteins
777:(symbol
775:Cysteine
706:+9.4° (H
360:E number
188:921-01-7
136:Cysteine
44:cytidine
40:cytisine
32:cytosine
6153:proline
6072:glycine
6051:glycine
6042:citrate
5961:alanine
5893:leucine
5765:(E927b)
5602:Colours
5484:(≈10.1)
5425:(≈12.5)
5419:(≈10.8)
5327:Glycine
5322:Proline
5317:Alanine
5306:Leucine
5253:Peptide
5248:Protein
5048:mercury
5038:cadmium
4989:Ethanol
4927:nitrite
4859:heparin
4558:Nervous
4197:Codeine
4171:opioids
3996:Cineole
3860:Bibcode
3742:3309557
3656:: 190.
3635:7569041
3600:9209528
3511:5924137
3503:4842541
3426:6440629
3403:Bibcode
3052:4303468
2965:1579111
2908:2885059
2803:. Wiley
2752:Bibcode
2700:5650851
2659:3298579
2637:J. Nutr
2538:3155927
2498:9636038
2463:2539629
2455:9202491
2435:Bibcode
2302:May 24,
2276:vrg.org
1995:8488618
1972:Bibcode
1719:monomer
1670:Cystine
1664:History
1514:keratin
1485:, is a
1418:Inteins
1410:ligases
1386:to the
1370:Insulin
1353:Cystine
1342:cytosol
1281:, will
1239:alanine
1233:and in
1223:sulfide
1207:glycine
1001:protein
912:by the
910:encoded
884:cystine
826:formula
756:what is
754: (
714:= 1.3)
669:Acidity
417:PubChem
309: (
221::
180:52-89-1
173:52-90-4
48:Sistine
36:cystine
6580:Thiols
6258:valine
6056:serine
5839:lysine
5771:(E928)
5759:(E927)
5753:(E926)
5747:(E925)
5741:(E924)
5735:(E923)
5729:(E922)
5723:(E921)
5714:(E920)
5643:&
5630:&
5616:&
5478:(≈8.3)
5472:(≈5.4)
5466:(≈4.1)
5460:(≈3.9)
5431:(≈6.1)
5417:Lysine
5389:Serine
5296:Valine
5169:WHO-EM
5135:Emetic
4794:system
4695:Oximes
4560:system
4480:WHO-EM
4227:Heroin
4054:Senega
3888:
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3740:
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1656:Safety
1440:, and
1397:. The
1295:codons
1209:, and
1141:plants
1106:serine
1066:Evonik
1049:kosher
971:gives
947:- and
914:codons
905:E920.
871:κύστη
839:. The
751:verify
748:
681:1.71 (
621:121.15
551:SMILES
405:D00026
313:-form)
269:ChEMBL
127:Names
6519:Other
6210:other
5668:Waxes
5504:types
5370:Polar
5081:Other
4877:Other
4549:V03AB
4305:Other
4166:Opium
4132:Mesna
3886:S2CID
3596:S2CID
3507:S2CID
2904:S2CID
2778:S2CID
2459:S2CID
2258:treyf
2196:S2CID
2120:S2CID
1717:of a
1715:dimer
1619:sheep
1613:Sheep
1554:In a
1139:. In
1053:halal
873:kýsti
869:Greek
841:thiol
687:thiol
506:InChI
365:E920
249:ChEBI
202:JSmol
46:, or
6503:see
5043:lead
3878:PMID
3738:PMID
3728:ISBN
3631:PMID
3588:PMID
3553:PMID
3499:PMID
3431:PMID
3345:ISBN
3294:PMID
3286:ISSN
3247:PMID
3239:ISSN
3200:PMID
3192:ISSN
3153:PMID
3145:ISSN
3104:PMID
3096:ISSN
3057:PMID
3039:ISSN
3000:PMID
2961:PMID
2943:ISSN
2896:PMID
2770:PMID
2696:PMID
2655:PMID
2612:ISBN
2589:PMID
2543:PMID
2494:PMID
2451:PMID
2375:ISBN
2328:2021
2304:2020
2283:2024
2188:PMID
2112:PMID
2039:ISSN
2000:PMID
1963:PNAS
1942:2012
1909:2018
1846:ISBN
1813:".
1791:ISBN
1510:hair
1452:and
1364:and
1317:and
1283:bind
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855:and
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441:UNII
430:5862
396:KEGG
385:4782
306:5653
3964:R05
3868:doi
3856:458
3829:CNH
3821:NSO
3720:doi
3697:doi
3681:N,S
3658:doi
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3580:doi
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3460:hdl
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892:Cyx
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984:R
982:(
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955:/
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939:/
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835:2
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816:/
813:n
807:ɪ
804:t
801:s
798:ɪ
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792:ˈ
789:/
783:C
746:N
712:c
708:2
702:)
700:D
698:(
676:a
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609:S
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603:O
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594:H
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588:C
477:)
473:(
311:L
242:C
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81:L
62:l
57:.
50:.
20:)
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