505:
649:
has been detected in mutagenesis experiments, in which the mutant PurT GAR transforymylase had a weak affinity for formate. Incubating PurT GAR transformylase with formyl phosphate, ADP, and GAR, yields both ATP and FGAR. This further indicating that formyl phosphate may be an intermediate, as it is kinetically and chemically competent to carry out the formylation reaction in the enzyme. An enzyme phosphate intermediate preceding the formylphosphate intermediate has also been proposed to form based on positional isotope exchange studies. However, structural data indicates that the formate may be positioned for a direct attack on the Îł-phosphate of ATP in the enzyme's active site to form the formylphosphate intermediate.
607:
730:, it is highly abundant and it is believed to have a role in the epigenetics of chromatin function. Lysines that are formylated have been shown to play a role in DNA binding. Additionally, formylation has been detected on histone lysines that are also known to be acetylated and methylated. Thus, formylation may block other post-translational modifications. Formylation is detected most frequently on 19 different modification sites on Histone H1. The genetic expression of the cell is highly disrupted by formylation, which may cause diseases such as cancer. The development of these modifications may be due to oxidative stress.
795:, has been used to identify a mutation in the gene coding for mitochondrial methionyl-tRNA formyltransferase (MTFMT) in patients with Leigh syndrome. The c.626C>T mutation identified in MTFMT yielding symptoms of Leigh Syndrome is believed to alter exon splicing leading to a frameshift mutation and a premature stop codon. Individuals with the MTFMT c.626C>T mutation were found to have reduced fMet-tRNAMet levels and changes in the formylation level of mitochondrically translated COX1. This link provides evidence for the necessity of formylated methionine in initiation of expression for certain mitochondrial genes.
734:
acetyl-lysine can be quickly outcompeted by the formation of formyl-lysine due to the high reactivity of formylphosphate species. This situation is currently believed to be caused by oxidative DNA damage. A mechanism for the formation of formylphosphate has been proposed, which it is highly dependent on oxidatively damaged DNA and mainly driven by radical chemistry within the cell. The formylphosphate produced can then be used to formylate lysine. Oxidative stress is believed to play a role in the availability of lysine residues in the surface of proteins and the possibility of being formylated.
616:
solvent. In the active site, Asn 106, His 108, and Asp 144 are positioned to assist with formyl transfer. However, mutagenesis studies have indicated that these residues are not individually essential for catalysis, as only mutations of two or more residues inhibit the enzyme. Based on the structure the negatively charged Asp144 is believed to increase the pKa of His108, allowing the protonated imidazolium group of His108 to enhances the electrophillicity of the N10-formyl-THF formyl group. Additionally, His108 and Asn106 are believed to stabilize the oxyanion formed in the transition state.
719:
275:
620:
653:
675:
687:
79:
738:
548:
700:
469:
33:
756:
1599:"Synthesis, biological and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-glycinamide ribonucleotide formyltransferase"
648:
A sequential mechanism has been proposed for PurT GAR transformylase in which a short lived formyl phosphate intermediate is proposed to first form. This formyl phosphate intermediate then undergoes nucleophilic attack by the GAR amine for transfer of the formyl group. A formyl phosphate intermediate
774:
and academic laboratories. Although similar in structure to N10-formyl-THF, lometrexol is incapable of carrying out one carbon transfer reactions. Additionally, several GAR based inhibitors of GAR transformylase have also been synthesized. Development of folate based inhibitors have been found to be
682:
The amine on AICAR is much less nucleophillic than its counterpart on GAR due to delocalization of electrons in AICAR through conjugation. Therefore, the N5 nucleophile of AIRCAR must be activated for the formylation reaction to occur. Histidine 268 and Lysine 267 have been found to be essential for
615:
The formylation reaction is proposed to occur through a direct transfer reaction in which the amine group of GAR nucleophilically attacks N10-formyl-THF creating a tetrahedral intermediate. As the α-amino group of GAR is relatively reactive, deprotonation of the nucleophile is proposed to occur by
610:
Active site of PurN GAR transformylased in a complex with the folate based inhibitor 5-deaza-5,6,7,8-tetrahydrofolate (5dTHF). The α-amino group of GAR (Pink) is located in a position which would attack a N10-formate group on the folate based inhibitor (yellow). Asn 106, His 108, and Asp 144 are
733:
In histone proteins, lysine is typically modified by
Histone Acetyl-Transferases (HATs) and Histone Deacetylases (HDAC or KDAC). The acetylation of lysine is fundamental to the regulation and expression of certain genes. Oxidative stress creates a significantly different environment in which
572:
catalyzes the formylation of GAR to formylglycinamidine ribotide (FGAR) in the fourth reaction of the pathway. In the penultimate step of de novo purine biosynthesis, 5-aminoimidazole-4-carboxyamide ribotide (AICAR) is formylated to 5-formaminoimidazole-4-carboxamide ribotide (FAICAR) by
597:
PurN GAR transformylase 1CDE uses the coenzyme N10-formyltetrahydrofolate (N10-formyl-THF) as a formyl donor to formylate the α-amino group of GAR. In eukaryotes, PurN GAR transformylase is part of a large multifunctional protein, but is found as a single protein in prokaryotes.
524:
in order to start protein synthesis. fMet possesses the same codon sequence as methionine. However, fMet is only used for the initiation of protein synthesis and is thus found only at the N terminus of the protein. Methionine is used during the rest translation. In
665:
AICAR transformylase requires the coenzyme N10-formyltetrahydrofolate (N10-formyl-THF) as the formyl donor for the formylation of AICAR to FAICAR. However, AICAR transformylase and GAR transformylase do not share a high sequence similarity or structural homology.
366:
Formylation can be applied to other aromatic rings. As it generally begins with nucleophilic attack by the aromatic group, the electron density of the ring is an important factor. Some aromatic compounds, such as pyrrole, are known to formylate regioselectively.
520:, and the enzyme methionyl-tRNA formyltransferase. This reaction is not used by eukaryotes or Archaea, as the presence of tRNA in non bacterial cells is dubbed as intrusive material and quickly eliminated. After its production, tRNA is delivered to the
770:. Several folate based inhibitors have been developed to inhibit formylation reactions by GAR transformylase and AICAR transformylase. The first GAR transformylase inhibitor Lometrexol was developed in the 1980s through a collaboration between
975:
Warashina, Takuya; Matsuura, Daisuke; Sengoku, Tetsuya; Takahashi, Masaki; Yoda, Hidemi; Kimura, Yoshikazu (16 October 2018). "Regioselective
Formylation of Pyrrole-2-Carboxylate: Crystalline Vilsmeier Reagent vs Dichloromethyl Alkyl Ether".
393:
of alkenes is the most important method for obtaining aliphatic formyls (i.e., aldehydes). The reaction is largely restricted to industrial settings. Several specialty methods exist for laboratory-scale synthesis, including the
790:
is a neurodegenerative disorder that has been linked to a defect in an enzymatic formylation reaction. Leigh syndrome is typically associated with defects in oxidative phosphorylation, which occurs in the mitochondria.
1668:
Tucker EJ, Hershman SG, Köhrer C, Belcher-Timme CA, Patel J, Goldberger OA, Christodoulou J, Silberstein JM, McKenzie M, Ryan MT, Compton AG, Jaffe JD, Carr SA, Calvo SE, RajBhandary UL, Thorburn DR, Mootha VK (2011).
683:
catalysis and are conserved in all AICAR transformylase. Histidine 268 is involved in deprotonation of the N5 nucleophile of AICAR, whereas Lysine 267 is proposed to stabilize the tetrahedral intermediate.
925:
Casiraghi, Giovanni; Casnati, Giuseppe; Puglia, Giuseppe; Sartori, Giovanni; Terenghi, Giuliana (1980). "Selective reactions between phenols and formaldehyde. A novel route to salicylaldehydes".
779:, which adds additional Îł-glutamates to monoglutamate folates and antifolates after entering the cell for increased enzyme affinity. This increased affinity can lead to antifolate resistance.
1359:
Marolewski, A.E.; Mattia, K.M.; Warren, M.S.; Benkovic, S.J. (1997). "Formyl phosphate: a proposed intermediate in the reaction catalyzed by
Escherichia coli PurT GAR transformylase".
589:. While the two enzymes have no sequence conservation and require different formyl donors, the specific activity and Km for GAR are the same in both PurT and PurN GAR transformylase.
1597:
Wang, L; Desmoulin, S.K.; Cherian, C.; Polin, L.; White, K.; Kushner, J.; Fulterer, A.; Chang, M.; Mitchell, S.; Stout, M.; Romero, M.F.; Hou, Z.; Matherly, L.H.; Gangjee, A (2011).
632:
PurT GAR transformylase requires formate as the formyl donor and ATP for catalysis. It has been estimated that PurT GAR transformylase carries out 14-50% of GAR formylations in
1751:
1321:
Thoden, J.B.; Firestine, S.; Nixon, A.; Benkovic, S.J.; Holden, H.M (2000). "Molecular
Structure of Escherichia coli PurT-Encoded Glycinamide Ribonucleotide Transformylase".
89:
refers to any chemical processes in which a compound is functionalized with a formyl group (-CH=O). In organic chemistry, the term is most commonly used with regards to
504:
112:
Formylation generally involves the use of formylation agents, reagents that give rise to the CHO group. Among the many formylation reagents, particularly important are
1399:"N-Formylation of lysine is a widespread post-translational modification of nuclear proteins occurring at residues involved in regulation of chromatin function"
320:), attributed to attraction between the phenoxide and the formylating reagent. Ionic interactions have been invoked for the cationic nitrogen centres in the
433:
by
Marcker and Sanger in 1964 and was later identified to be involved in the initiation of protein synthesis in bacteria and organelles. The formation of
403:
585:
PurN GAR transformylase is found in eukaryotes and prokaryotes. However, a second GAR transformylase, PurT GAR transformylase has been identified in
2582:
1744:
726:
Formylation has been identified on the Nε of lysine residues in histones and proteins. This modification has been observed in linker histones and
282:
606:
1737:
1283:
Wolan, D; Greasley, S.E.; Beardsley, P.; Wilson, I.A. (2002). "Structural
Insights into the Avian AICAR Transformylase Mechanism".
355:
is possible via the
Casiraghi formylation, but other methods apply masked forms of formaldehyde, in part to limit the formation of
766:
Cancer cells require high concentrations of purines to facilitate division and tend to rely on de novo synthesis rather than the
708:
441:
429:
Formylation has been identified in several critical biological processes. Methionine was first discovered to be formylated in
1764:
359:. Aldehydes are strongly deactivating and as such phenols typically only react once. However certain reactions, such as the
948:
Lindoy, Leonard F. (July 1998). "Mono- and
Diformylation of 4-Substituted Phenols: A New Application of the Duff Reaction".
321:
102:
2414:
727:
399:
763:
Inhibition of enzymes involved in purine biosynthesis has been exploited as a potential drug target for chemotherapy.
379:
333:
252:
345:
718:
418:
is termed "formylation". A formyl functional group consists of a carbonyl bonded to hydrogen. When attached to an
2454:
1865:
1760:
1562:
Christopherson, R.I.; Lyons, S.D.; Wilson, P.K (2002). "Inhibitors of de Novo
Nucleotide Biosynthesis as Drugs".
541:
517:
356:
1729:
678:
1M9N Active site of AICAR transformylase. Lys267 (cyan), His268 (purple), AICAR (green). Rendered from PDB 1M9N.
274:
375:
216:
189:
2508:
415:
247:
54:
2392:
1448:"N-formylation of lysine in histone proteins as a secondary modification arising from oxidative DNA damage"
195:
185:
42:
1671:"Mutations in MTFMT underlie a human disorder of formylation causing impaired mitochondrial translation"
565:
521:
513:
508:
Methionyl tRNAfMet transformylase complexed with initiator formylmethionyl tRNA. Rendered from PDB 2FMT.
337:
619:
1783:
1459:
1059:
574:
453:
1798:
674:
652:
1870:
1510:"Discovery of a Potent, Nonpolyglutamatable Inhibitor of Glycinamide Ribonucleotide Transformylase"
1228:
537:
445:
371:
225:
2219:
686:
2209:
2113:
1963:
1721:
1251:
993:
767:
569:
449:
434:
341:
256:
737:
512:
In bacteria and organelles, the initiation of protein synthesis is signaled by the formation of
547:
78:
2577:
2067:
1953:
1912:
1700:
1628:
1579:
1539:
1487:
1428:
1376:
1338:
1300:
1202:
1141:
1087:
1028:
907:
530:
395:
229:
212:
203:
181:
121:
106:
90:
2370:
2348:
2247:
2166:
2057:
2034:
1958:
1930:
1690:
1682:
1618:
1610:
1571:
1529:
1521:
1477:
1467:
1418:
1410:
1368:
1330:
1292:
1243:
1192:
1131:
1123:
1077:
1067:
1020:
985:
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930:
899:
868:
838:
804:
792:
699:
390:
352:
263:
233:
129:
125:
59:
2481:
2181:
2072:
1948:
1907:
1112:"Comparison of Initiation of Protein synthesis in Procaryotes, Eucaryotes, and Organelles"
317:
208:
117:
536:
Once protein synthesis is accomplished, the formyl group on methionine can be removed by
1463:
1063:
722:
Formylation of lysine can compete with acetylation as a post-translational modification.
2343:
2237:
2214:
2156:
2006:
1988:
1875:
1841:
1695:
1670:
1623:
1598:
1534:
1509:
1482:
1447:
1423:
1398:
809:
787:
489:
485:
473:
1136:
1111:
1082:
1047:
1024:
829:
Olah, George A.; Ohannesian, Lena.; Arvanaghi, Massoud. (1987). "Formylating agents".
2571:
2362:
2307:
2289:
2265:
2204:
2199:
2151:
2146:
2095:
2052:
1973:
1917:
1821:
997:
533:, as the formyl group blocks peptide bond formation at the N-terminus of methionine.
360:
325:
199:
1255:
468:
17:
2161:
1978:
1793:
1778:
481:
237:
98:
703:
Formylation is a post-translational modification which occurs on lysine residues.
2283:
2242:
2171:
2136:
2131:
2090:
2062:
2029:
2011:
1983:
1836:
1816:
1788:
1197:
1180:
1127:
856:
776:
176:
113:
1686:
564:
Two formylation reactions are required in the eleven step de novo synthesis of
2523:
2429:
2406:
2402:
2358:
2322:
2299:
2082:
1886:
1852:
1808:
555:-formylmethionine is catalyzed by the enzyme methionyl-tRNA formyltransferase.
419:
294:
243:
989:
378:. These involve strong acid catalysis and proceed in a manner similar to the
2552:
2465:
2275:
2194:
2141:
2105:
2044:
2021:
1968:
1899:
1831:
1472:
1247:
771:
712:
637:
290:
145:
1704:
1632:
1583:
1543:
1491:
1432:
1342:
1304:
1032:
911:
903:
1414:
1380:
1206:
1145:
1091:
1072:
2540:
2536:
2532:
2469:
2442:
2384:
2335:
2331:
2229:
2176:
1998:
1940:
1922:
934:
775:
particularly challenging as the inhibitors also down regulate the enzyme
423:
306:
137:
961:
872:
842:
2500:
2492:
2473:
2446:
2257:
755:
493:
457:
329:
302:
298:
221:
153:
94:
1614:
1575:
1525:
1508:
DeMartino, J.K.; Hwang, I.; Xu, L.; Wilson, I.A.; Boger, D.L. (2006).
1372:
1334:
1296:
2544:
2496:
2438:
2380:
2123:
1895:
305:
will react under aggressive conditions but deactivated rings such as
286:
133:
2189:
1860:
1227:
Warren, M.S.; K.M. Mattia; A.E. Marolewski; S.J. Benkovic (1996).
754:
736:
717:
698:
685:
673:
651:
618:
605:
546:
503:
77:
1446:
Jiang, T; Zhou, X.; Taghizadeh, K.; Dong, M.; Dedon, PC. (2007).
1181:"Biochemistry of Methanogenesis: a Tribute to Marjory Stephenson"
289:
are a common substrate, as they readily deprotonate to excellent
336:; coordination to high oxidation metals has been invoked in the
105:). In biochemistry the reaction is catalysed by enzymes such as
1733:
1646:
741:
Formyl phosphate is a proposed product of oxidative DNA damage.
454:
5-aminoimidazole-4-carboxyamide ribotide (AICAR) transformylase
285:
and therefore work best with electron-rich starting materials.
1048:"N-Formylmethionyl-sRNA as the initiator of protein synthesis"
859:; Ohannesian, L.; Arvanaghi, M. (1987). "Formylating agents".
540:. The methionine residue can be further removed by the enzyme
26:
711:
that occur on histone proteins, which been shown to modulate
273:
1229:"The transformylase enzymes of de novo purine biosynthesis"
1011:
Marcker, K; Sanger, F. (1964). "N-formyl-methionyl-S-RNA".
568:, the precursor of the purine ribonucleotides AMP and GMP.
456:. More recently, formylation has been discovered to be a
301:, or fused aromatic rings can also be expected to react.
2482:
4-(p-hydroxybenzylidene)-5-imidazolinone (HBI) formation
444:. Additionally, two formylation reactions occur in the
293:
nucleophiles. Other electron-rich substrates, such as
1557:
1555:
1553:
927:
Journal of the
Chemical Society, Perkin Transactions 1
266:, which converts alkenes to the homologated aldehyde.
370:
Formylation of benzene rings can be achieved via the
168:
A reagent that delivers the formyl group is called a
890:-Dimethylformamide: A Multipurpose Building Block".
2531:
2521:
2491:
2464:
2437:
2427:
2401:
2379:
2357:
2330:
2320:
2298:
2274:
2256:
2228:
2122:
2104:
2081:
2043:
2020:
1997:
1939:
1894:
1884:
1851:
1807:
1771:
228:. This method synthesizes aromatic aldehydes using
40:It has been suggested that this article should be
2455:p-Hydroxybenzylidene-imidazolinone (HBI) formation
1354:
1352:
460:modification, which may modulate gene expression.
1503:
1501:
1397:Wisniewski, J.R.; Zougman, A.; Mann, M. (2002).
312:Many formylation reactions will select only the
262:A particularly important formylation process is
570:Glycinamide ribonucleotide (GAR) transformylase
450:glycinamide ribonucleotide (GAR) transformylase
448:. These reactions are catalyzed by the enzymes
1316:
1314:
1222:
1220:
1218:
1216:
1745:
1392:
1390:
1278:
1276:
1274:
1272:
656:Reaction catalyzed by PurT GAR transformylase
476:, showing initial formylation of methanofuran
8:
2415:Tryptophan tryptophylquinone (TTQ) formation
560:Formylation reactions in purine biosynthesis
1105:
1103:
1101:
690:Mechanism catalyzed by AICAR transformylase
2528:
2434:
2327:
1891:
1752:
1738:
1730:
978:Organic Process Research & Development
240:) in the presence of Lewis acid catalysts:
136:group (-CH=O). The reaction is a route to
1694:
1622:
1533:
1481:
1471:
1422:
1196:
1135:
1081:
1071:
82:Formyl functional group is shown in blue.
1166:Fundamentals of Biochemistry 3rd edition
488:cycle. The formyl group is derived from
467:
309:are difficult to formylate effectively.
2509:Methylidene-imidazolone (MIO) formation
1159:
1157:
1155:
821:
351:The direct reaction between phenol and
751:Formylation reactions as a drug target
611:colored green. Rendered from PDB 1CDE.
516:(tRNA). This reaction is dependent on
404:Bodroux–Chichibabin aldehyde synthesis
2393:Lysine tyrosylquinone (LTQ) formation
1649:. Online Mendelian Inheritance in Man
529:, tRNA is specifically recognized by
236:(or another metallic cyanide as such
7:
1046:Adams, J.M.; Capecchi, M.R. (1966).
623:Mechanism of PurN GAR transformylase
281:Formylation reactions are a form of
1866:Glycosyl phosphatidylinositol (GPI)
715:conformations and gene activation.
414:In biochemistry, the addition of a
283:electrophilic aromatic substitution
25:
2177:Oxidative deamination to aldehyde
759:Chemical structure of lometrexol
709:post-translational modifications
636:. The enzyme is a member of the
500:Formylation in protein synthesis
410:Formylation reactions in biology
31:
2583:Post-translational modification
1765:posttranslational modifications
695:Formylation in histone proteins
446:de novo biosynthesis of purines
93:(for example the conversion of
1603:Journal of Medicinal Chemistry
1514:Journal of Medicinal Chemistry
422:, a formyl group is called an
1:
1025:10.1016/S0022-2836(64)80164-9
707:ε-Formylation is one of many
442:methionyl-tRNA transformylase
328:, and the electron-deficient
886:Ding, S.; Jiao, N. (2012). "
728:high mobility group proteins
400:Bouveault aldehyde synthesis
363:, can give double addition.
120:. A formylation reaction in
1984:Topaquinone (TPQ) formation
1198:10.1099/00221287-144-9-2377
1128:10.1128/MMBR.47.1.1-45.1983
566:inosine monophosphate (IMP)
522:30S subunit of the ribosome
440:is catalyzed by the enzyme
253:Dichloromethyl methyl ether
2599:
1687:10.1016/j.cmet.2011.07.010
777:folypolyglutamate synthase
768:nucleotide salvage pathway
551:The chemical synthesis of
357:phenol formaldehyde resins
2428:Crosslinks between three
1761:Protein primary structure
640:superfamily of proteins.
542:methionine aminopeptidase
518:10-formyltetrahydrofolate
132:is functionalized with a
2522:Crosslinks between four
990:10.1021/acs.oprd.8b00233
376:Gattermann-Koch reaction
322:Vilsmeier–Haack reaction
217:Gattermann-Koch reaction
190:Vilsmeier-Haack reaction
103:Gattermann–Koch reaction
2321:Crosslinks between two
1473:10.1073/pnas.0606775103
1248:10.1351/pac199668112029
1116:Microbiological Reviews
746:Formylation in medicine
628:PurT GAR transformylase
593:PurN GAR transformylase
416:formyl functional group
380:Friedel–Crafts reaction
334:Reimer-Tiemann reaction
248:Reimer-Tiemann reaction
1969:Porphyrin ring linkage
1403:Nucleic Acids Research
1179:Thauer, R. K. (1998).
1164:Voet and Voet (2008).
904:10.1002/anie.201200859
760:
742:
723:
704:
691:
679:
657:
624:
612:
556:
531:initiation factor IF-2
509:
477:
346:Kolbe–Schmitt reaction
278:
196:Hexamethylenetetramine
186:phosphorus oxychloride
83:
55:Formylation in biology
2030:Succinimide formation
1073:10.1073/pnas.55.1.147
758:
740:
721:
702:
689:
677:
655:
622:
609:
550:
514:formyl-methionyl-tRNA
507:
471:
386:Aliphatic formylation
277:
81:
46:into articles titled
1784:Protein biosynthesis
935:10.1039/P19800001862
892:Angew. Chem. Int. Ed
661:AICAR transformylase
575:AICAR transformylase
492:and is converted to
270:Aromatic formylation
18:Formylation reaction
1464:2007PNAS..104...60J
1415:10.1093/nar/gkm1057
1291:(52): 15505–15513.
1064:1966PNAS...55..147A
962:10.1055/s-1998-2110
873:10.1021/cr00080a001
843:10.1021/cr00080a001
538:peptide deformylase
372:Gattermann reaction
342:Rieche formylations
226:Gattermann reaction
2114:Transglutamination
1168:. New York: Wiley.
761:
743:
724:
705:
692:
680:
658:
625:
613:
581:GAR transformylase
557:
510:
478:
279:
257:Rieche formylation
164:Formylation agents
107:formyltransferases
91:aromatic compounds
84:
2565:
2564:
2561:
2560:
2517:
2516:
2423:
2422:
2316:
2315:
2068:Polyglutamylation
1954:Dephosphorylation
1913:Dephosphorylation
1725:-Formylmethionine
1615:10.1021/jm200739e
1609:(20): 7150–7164.
1576:10.1021/ar0000509
1526:10.1021/jm0601147
1520:(10): 2998–3002.
1373:10.1021/bi962961p
1367:(22): 6709–6716.
1335:10.1021/bi000926j
1329:(30): 8791–8802.
1297:10.1021/bi020505x
1242:(11): 2029–2036.
1110:Kozak, M (1983).
898:(37): 9226–9237.
438:-formylmethionine
396:Sommelet reaction
230:hydrogen chloride
213:hydrochloric acid
204:Sommelet reaction
182:Dimethylformamide
170:formylating agent
126:organic reactions
122:organic chemistry
76:
75:
16:(Redirected from
2590:
2529:
2435:
2371:Sulfilimine bond
2349:ADP-ribosylation
2328:
2248:ADP-ribosylation
2167:ADP-ribosylation
2058:ADP-ribosylation
2035:ADP-ribosylation
1959:ADP-ribosylation
1931:ADP-ribosylation
1892:
1885:Single specific
1754:
1747:
1740:
1731:
1709:
1708:
1698:
1665:
1659:
1658:
1656:
1654:
1647:"Leigh Syndrome"
1643:
1637:
1636:
1626:
1594:
1588:
1587:
1559:
1548:
1547:
1537:
1505:
1496:
1495:
1485:
1475:
1443:
1437:
1436:
1426:
1394:
1385:
1384:
1356:
1347:
1346:
1318:
1309:
1308:
1280:
1267:
1266:
1264:
1262:
1233:
1224:
1211:
1210:
1200:
1176:
1170:
1169:
1161:
1150:
1149:
1139:
1107:
1096:
1095:
1085:
1075:
1043:
1037:
1036:
1008:
1002:
1001:
972:
966:
965:
956:(7): 1029–1032.
945:
939:
938:
922:
916:
915:
883:
877:
876:
853:
847:
846:
831:Chemical Reviews
826:
805:Hydroformylation
793:Exome sequencing
391:Hydroformylation
353:paraformaldehyde
264:hydroformylation
234:hydrogen cyanide
130:organic compound
71:
68:
35:
34:
27:
21:
2598:
2597:
2593:
2592:
2591:
2589:
2588:
2587:
2568:
2567:
2566:
2557:
2513:
2487:
2460:
2419:
2397:
2375:
2353:
2312:
2308:C-mannosylation
2294:
2270:
2252:
2224:
2190:Imine formation
2118:
2100:
2077:
2073:Polyglycylation
2039:
2016:
1993:
1949:Phosphorylation
1935:
1908:Phosphorylation
1880:
1847:
1803:
1767:
1758:
1718:
1713:
1712:
1667:
1666:
1662:
1652:
1650:
1645:
1644:
1640:
1596:
1595:
1591:
1570:(11): 961–971.
1561:
1560:
1551:
1507:
1506:
1499:
1445:
1444:
1440:
1396:
1395:
1388:
1358:
1357:
1350:
1320:
1319:
1312:
1282:
1281:
1270:
1260:
1258:
1236:Pure Appl. Chem
1231:
1226:
1225:
1214:
1178:
1177:
1173:
1163:
1162:
1153:
1109:
1108:
1099:
1045:
1044:
1040:
1010:
1009:
1005:
974:
973:
969:
947:
946:
942:
924:
923:
919:
885:
884:
880:
855:
854:
850:
828:
827:
823:
818:
801:
785:
753:
748:
697:
672:
663:
646:
630:
604:
595:
583:
562:
502:
480:Formylation of
466:
412:
388:
318:salicylaldehyde
272:
209:Carbon monoxide
166:
118:carbon monoxide
72:
66:
63:
36:
32:
23:
22:
15:
12:
11:
5:
2596:
2594:
2586:
2585:
2580:
2570:
2569:
2563:
2562:
2559:
2558:
2556:
2555:
2549:
2547:
2526:
2519:
2518:
2515:
2514:
2512:
2511:
2505:
2503:
2489:
2488:
2486:
2485:
2478:
2476:
2462:
2461:
2459:
2458:
2451:
2449:
2432:
2425:
2424:
2421:
2420:
2418:
2417:
2411:
2409:
2399:
2398:
2396:
2395:
2389:
2387:
2377:
2376:
2374:
2373:
2367:
2365:
2355:
2354:
2352:
2351:
2346:
2344:Disulfide bond
2340:
2338:
2325:
2318:
2317:
2314:
2313:
2311:
2310:
2304:
2302:
2296:
2295:
2293:
2292:
2287:
2280:
2278:
2272:
2271:
2269:
2268:
2262:
2260:
2254:
2253:
2251:
2250:
2245:
2240:
2238:Citrullination
2234:
2232:
2226:
2225:
2223:
2222:
2217:
2215:Propionylation
2212:
2207:
2202:
2197:
2192:
2187:
2185:-glycosylation
2179:
2174:
2169:
2164:
2159:
2157:Ubiquitination
2154:
2149:
2144:
2139:
2134:
2128:
2126:
2120:
2119:
2117:
2116:
2110:
2108:
2102:
2101:
2099:
2098:
2093:
2087:
2085:
2079:
2078:
2076:
2075:
2070:
2065:
2060:
2055:
2049:
2047:
2041:
2040:
2038:
2037:
2032:
2026:
2024:
2018:
2017:
2015:
2014:
2009:
2007:Palmitoylation
2003:
2001:
1995:
1994:
1992:
1991:
1989:Detyrosination
1986:
1981:
1979:Flavin linkage
1976:
1971:
1966:
1961:
1956:
1951:
1945:
1943:
1937:
1936:
1934:
1933:
1928:
1920:
1915:
1910:
1904:
1902:
1889:
1882:
1881:
1879:
1878:
1876:Detyrosination
1873:
1868:
1863:
1857:
1855:
1849:
1848:
1846:
1845:
1842:Myristoylation
1839:
1834:
1829:
1824:
1819:
1813:
1811:
1805:
1804:
1802:
1801:
1799:N–O acyl shift
1796:
1791:
1786:
1781:
1775:
1773:
1769:
1768:
1759:
1757:
1756:
1749:
1742:
1734:
1728:
1727:
1717:
1714:
1711:
1710:
1681:(3): 428–434.
1660:
1638:
1589:
1564:Acc. Chem. Res
1549:
1497:
1438:
1409:(2): 570–577.
1386:
1348:
1310:
1268:
1212:
1171:
1151:
1097:
1058:(1): 147–155.
1038:
1019:(6): 835–840.
1003:
984:(4): 614–618.
967:
940:
917:
878:
867:(4): 671–686.
848:
837:(4): 671–686.
820:
819:
817:
814:
813:
812:
810:Hydroacylation
807:
800:
797:
788:Leigh syndrome
784:
783:Leigh syndrome
781:
752:
749:
747:
744:
696:
693:
671:
668:
662:
659:
645:
642:
629:
626:
603:
600:
594:
591:
582:
579:
561:
558:
501:
498:
490:carbon dioxide
486:methanogenesis
484:initiates the
474:methanogenesis
465:
464:Methanogenesis
462:
411:
408:
387:
384:
316:product (e.g.
271:
268:
260:
259:
250:
241:
219:
206:
193:
179:
165:
162:
154:formate esters
74:
73:
39:
37:
30:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2595:
2584:
2581:
2579:
2576:
2575:
2573:
2554:
2551:
2550:
2548:
2546:
2542:
2538:
2534:
2530:
2527:
2525:
2520:
2510:
2507:
2506:
2504:
2502:
2498:
2494:
2490:
2484:(chromophore)
2483:
2480:
2479:
2477:
2475:
2471:
2467:
2463:
2457:(chromophore)
2456:
2453:
2452:
2450:
2448:
2444:
2440:
2436:
2433:
2431:
2426:
2416:
2413:
2412:
2410:
2408:
2404:
2400:
2394:
2391:
2390:
2388:
2386:
2382:
2378:
2372:
2369:
2368:
2366:
2364:
2363:Hydroxylysine
2360:
2356:
2350:
2347:
2345:
2342:
2341:
2339:
2337:
2333:
2329:
2326:
2324:
2319:
2309:
2306:
2305:
2303:
2301:
2297:
2291:
2290:Adenylylation
2288:
2285:
2282:
2281:
2279:
2277:
2273:
2267:
2266:Hydroxylation
2264:
2263:
2261:
2259:
2255:
2249:
2246:
2244:
2241:
2239:
2236:
2235:
2233:
2231:
2227:
2221:
2218:
2216:
2213:
2211:
2208:
2206:
2205:Succinylation
2203:
2201:
2200:Carbamylation
2198:
2196:
2193:
2191:
2188:
2186:
2184:
2180:
2178:
2175:
2173:
2170:
2168:
2165:
2163:
2160:
2158:
2155:
2153:
2152:Hydroxylation
2150:
2148:
2147:Adenylylation
2145:
2143:
2140:
2138:
2135:
2133:
2130:
2129:
2127:
2125:
2121:
2115:
2112:
2111:
2109:
2107:
2103:
2097:
2096:Glycosylation
2094:
2092:
2089:
2088:
2086:
2084:
2080:
2074:
2071:
2069:
2066:
2064:
2061:
2059:
2056:
2054:
2053:Carboxylation
2051:
2050:
2048:
2046:
2042:
2036:
2033:
2031:
2028:
2027:
2025:
2023:
2019:
2013:
2010:
2008:
2005:
2004:
2002:
2000:
1996:
1990:
1987:
1985:
1982:
1980:
1977:
1975:
1974:Adenylylation
1972:
1970:
1967:
1965:
1962:
1960:
1957:
1955:
1952:
1950:
1947:
1946:
1944:
1942:
1938:
1932:
1929:
1927:
1925:
1921:
1919:
1918:Glycosylation
1916:
1914:
1911:
1909:
1906:
1905:
1903:
1901:
1897:
1893:
1890:
1888:
1883:
1877:
1874:
1872:
1871:O-methylation
1869:
1867:
1864:
1862:
1859:
1858:
1856:
1854:
1850:
1843:
1840:
1838:
1835:
1833:
1830:
1828:
1825:
1823:
1822:Carbamylation
1820:
1818:
1815:
1814:
1812:
1810:
1806:
1800:
1797:
1795:
1792:
1790:
1787:
1785:
1782:
1780:
1777:
1776:
1774:
1770:
1766:
1762:
1755:
1750:
1748:
1743:
1741:
1736:
1735:
1732:
1726:
1724:
1720:
1719:
1715:
1706:
1702:
1697:
1692:
1688:
1684:
1680:
1676:
1672:
1664:
1661:
1648:
1642:
1639:
1634:
1630:
1625:
1620:
1616:
1612:
1608:
1604:
1600:
1593:
1590:
1585:
1581:
1577:
1573:
1569:
1565:
1558:
1556:
1554:
1550:
1545:
1541:
1536:
1531:
1527:
1523:
1519:
1515:
1511:
1504:
1502:
1498:
1493:
1489:
1484:
1479:
1474:
1469:
1465:
1461:
1457:
1453:
1449:
1442:
1439:
1434:
1430:
1425:
1420:
1416:
1412:
1408:
1404:
1400:
1393:
1391:
1387:
1382:
1378:
1374:
1370:
1366:
1362:
1355:
1353:
1349:
1344:
1340:
1336:
1332:
1328:
1324:
1317:
1315:
1311:
1306:
1302:
1298:
1294:
1290:
1286:
1279:
1277:
1275:
1273:
1269:
1257:
1253:
1249:
1245:
1241:
1237:
1230:
1223:
1221:
1219:
1217:
1213:
1208:
1204:
1199:
1194:
1191:: 2377–2406.
1190:
1186:
1182:
1175:
1172:
1167:
1160:
1158:
1156:
1152:
1147:
1143:
1138:
1133:
1129:
1125:
1121:
1117:
1113:
1106:
1104:
1102:
1098:
1093:
1089:
1084:
1079:
1074:
1069:
1065:
1061:
1057:
1053:
1049:
1042:
1039:
1034:
1030:
1026:
1022:
1018:
1014:
1007:
1004:
999:
995:
991:
987:
983:
979:
971:
968:
963:
959:
955:
951:
944:
941:
936:
932:
928:
921:
918:
913:
909:
905:
901:
897:
893:
889:
882:
879:
874:
870:
866:
862:
858:
852:
849:
844:
840:
836:
832:
825:
822:
815:
811:
808:
806:
803:
802:
798:
796:
794:
789:
782:
780:
778:
773:
769:
764:
757:
750:
745:
739:
735:
731:
729:
720:
716:
714:
710:
701:
694:
688:
684:
676:
669:
667:
660:
654:
650:
643:
641:
639:
635:
627:
621:
617:
608:
601:
599:
592:
590:
588:
580:
578:
576:
571:
567:
559:
554:
549:
545:
543:
539:
534:
532:
528:
523:
519:
515:
506:
499:
497:
495:
491:
487:
483:
475:
470:
463:
461:
459:
455:
451:
447:
443:
439:
437:
432:
427:
425:
421:
417:
409:
407:
405:
401:
397:
392:
385:
383:
381:
377:
373:
368:
364:
362:
361:Duff reaction
358:
354:
349:
347:
343:
339:
335:
331:
327:
326:Duff reaction
323:
319:
315:
310:
308:
304:
300:
296:
292:
288:
284:
276:
269:
267:
265:
258:
254:
251:
249:
245:
242:
239:
235:
231:
227:
223:
220:
218:
214:
210:
207:
205:
201:
200:Duff reaction
197:
194:
191:
187:
183:
180:
178:
175:
174:
173:
171:
163:
161:
159:
155:
151:
147:
143:
139:
135:
131:
127:
123:
119:
115:
110:
108:
104:
100:
96:
92:
88:
80:
70:
67:February 2023
61:
57:
56:
51:
50:
45:
44:
38:
29:
28:
19:
2220:Butyrylation
2182:
1923:
1826:
1794:Racemization
1779:Peptide bond
1722:
1678:
1674:
1663:
1651:. Retrieved
1641:
1606:
1602:
1592:
1567:
1563:
1517:
1513:
1458:(1): 60–65.
1455:
1451:
1441:
1406:
1402:
1364:
1361:Biochemistry
1360:
1326:
1323:Biochemistry
1322:
1288:
1285:Biochemistry
1284:
1259:. Retrieved
1239:
1235:
1188:
1185:Microbiology
1184:
1174:
1165:
1119:
1115:
1055:
1051:
1041:
1016:
1013:J. Mol. Biol
1012:
1006:
981:
977:
970:
953:
949:
943:
926:
920:
895:
891:
887:
881:
864:
860:
851:
834:
830:
824:
786:
765:
762:
732:
725:
706:
681:
664:
647:
633:
631:
614:
596:
586:
584:
563:
552:
535:
526:
511:
482:methanofuran
479:
435:
430:
428:
413:
389:
369:
365:
350:
313:
311:
280:
261:
238:zinc cyanide
169:
167:
157:
152:-CH=O), and
149:
141:
128:in which an
111:
99:benzaldehyde
87:,Formylation
86:
85:
64:
53:
48:
47:
41:
2284:Diphthamide
2243:Methylation
2210:Lactylation
2172:Deamination
2162:Sumoylation
2137:Acetylation
2132:Methylation
2091:Deamidation
2063:Methylation
2012:Prenylation
1837:Methylation
1827:Formylation
1817:Acetylation
1789:Proteolysis
1653:24 February
1261:24 February
1122:(1): 1–45.
857:Olah, G. A.
177:Formic acid
114:formic acid
49:Formylation
2572:Categories
2407:Tryptophan
2403:Tryptophan
2359:Methionine
2300:Tryptophan
2083:Asparagine
1853:C terminus
1809:N terminus
1675:Cell Metab
816:References
472:Cycle for
295:mesitylene
244:Chloroform
146:formamides
124:refers to
2553:Desmosine
2466:Histidine
2286:formation
2276:Histidine
2195:Glycation
2142:Acylation
2106:Glutamine
2045:Glutamate
2022:Aspartate
1964:Sulfation
1900:Threonine
1861:Amidation
1832:Glycation
998:106209464
950:Synthesis
861:Chem. Rev
772:Eli Lilly
713:chromatin
670:Mechanism
644:Mechanism
638:ATP-grasp
602:Mechanism
338:Casiraghi
291:phenoxide
138:aldehydes
2578:Proteins
2541:Allysine
2537:Allysine
2533:Allysine
2470:Tyrosine
2443:Tyrosine
2385:Tyrosine
2336:Cysteine
2332:Cysteine
2230:Arginine
1999:Cysteine
1941:Tyrosine
1716:See also
1705:21907147
1633:21879757
1584:12437321
1544:16686541
1492:17190813
1433:18056081
1343:10913290
1305:12501179
1256:39555269
1033:14187409
929:: 1862.
912:22930476
799:See also
424:aldehyde
307:pyridine
222:Cyanides
202:and the
160:-CH=O).
144:-CH=O),
2501:Glycine
2493:Alanine
2474:Glycine
2447:Glycine
2258:Proline
1926:-GlcNAc
1772:General
1696:3486727
1624:3209708
1535:2531195
1483:1765477
1460:Bibcode
1424:2241850
1381:9184151
1207:9782487
1146:6343825
1092:5328638
1060:Bibcode
634:E. coli
587:E. coli
527:E. coli
494:methane
458:histone
431:E. coli
420:R group
332:in the
330:carbene
303:Benzene
299:pyrrole
287:Phenols
246:in the
224:in the
215:in the
198:in the
188:in the
101:in the
95:benzene
60:discuss
2545:Lysine
2497:Serine
2439:Serine
2381:Lysine
2124:Lysine
1896:Serine
1703:
1693:
1631:
1621:
1582:
1542:
1532:
1490:
1480:
1431:
1421:
1379:
1341:
1303:
1254:
1205:
1144:
1137:281560
1134:
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