337:
462:
449:
405:
1524:
2509:
196:
1518:
50:
314:
121:
1530:
470:
thereof the active peptide beyond increasing CNS penetration. The innate utilization of sugars as solubilizing moieties in Phase II and III metabolism (glucuronic acids) has remarkably allowed an evolutionary advantage in that mammalian enzymes are not directly evolved to degrade O glycosylated products on larger moieties.
474:
of the plasma membrane. "Hop diffusion" notably combines free diffusion and intercomparmental transitions. Recent examples notably include high permeability of met-enkephalin analogs amongst other peptides. The full mOR agonist pentapeptide DAMGO is also CNS penetrant upon introduction of glycosylation.
513:
nucelobase gets to act like a leaving group. The intermediate produced is a similar oxacarbenium ion where both the hydroxy groups and the nucleobase are still attached to the anomeric carbon. Both mechanisms theoretically yield the same product. Most ribonucleotides are hydrolyzed via the concerted S
512:
ion intermediate. This intermediate rapidly reacts with the nearby water molecule to substitute the N-glycosidic bond of the ribose and the nucleobase with an O-glycosidic bond with a hydroxy group. The concerted mechanism, the water acts as a nucleophile and attacks at the anomeric carbon before the
520:
These reactions are practically irreversible. Due to the fact that the cleavage of the N-glycosidic bond from the DNA backbone can lead to detrimental mutagenic and cytotoxic responses in an organism, have the ability to also catalyze the synthesis of N-glycosidic bonds by way of an abasic DNA site
487:
carbon of the ribose sugar structure through an N-glycosidic bond. Occasionally, the nucleobases attached to the ribose undergo deamination, alkylation, or oxidation which results in cytotoxic lesions along the DNA backbone. These modifications severely threaten the cohesiveness of the DNA molecule,
473:
The peculiar nature of O-linked glycopeptides is that there are numerous examples which are CNS penetrant. The fundamental basis of this effect is thought to involve "membrane hopping" or "hop diffusion". The non-brownian motion driven "hop diffusion" process is thought to occur due to discontinuity
416:
Different biocatalytic approaches have been developed toward the synthesis of glycosides in the past decades, which using "glycosyltransferases" and "glycoside hydrolases" are among the most common catalysis. The former often needs expensive materials and the later often shows low yields, De Winter
441:
Fluorine directed glycosylations represent an encouraging handle for both B selectivity and introduction of a non-natural biomimetic C2 functionality on the carbohydrate. One innovative example provided by Bucher et al. provides a way to utilize a fluoro oxonium ion and the trichloroacetimidate to
437:
The highly substrate specific nature of the selectivity and the overall activity of the pyranoside can provide major synthetic difficulties. The overall specificity of the glycosylation can be improved by utilizing approaches which take into account the relative transition states that the anomeric
304:
which brominates at the 5-position. On addition of the alcohol ROH and lithium carbonate, the OR replaces the bromine and on deprotecting the acetylated hydroxyls the product is synthesized in relatively high purity. It was suggested by Joshi et al. (2001) that lithium acts as the nucleophile that
438:
carbon can undergo during a typical glycosylation. Most notably, recognition and incorporation of Felkin-Ahn-Eisenstein models into rationale chemical design can generally provide reliable results provided the transformation can undergo this type of conformational control in the transition state.
332:
that break glycosidic bonds. Glycoside hydrolases typically can act either on α- or on β-glycosidic bonds, but not on both. This specificity allows researchers to obtain glycosides in high epimeric excess, one example being Wen-Ya Lu's conversion of D-Glucose to Ethyl β-D-glucopyranoside using
469:
O-linked glycopeptides recently have been shown to exhibit excellent CNS permeability and efficacy in multiple animal models with disease states. In addition one of the most intriguing aspects thereof is the capability of O-glycosylation to extend half life, decrease clearance, and improve PK/PD
107:
The term 'glycoside' is now extended to also cover compounds with bonds formed between hemiacetal (or hemiketal) groups of sugars and several chemical groups other than hydroxyls, such as -SR (thioglycosides), -SeR (selenoglycosides), -NRR (N-glycosides), or even -CRRR (C-glycosides).
309:
the alcohol is substituted for the bromine group. Advantages of this method as well as its stereoselectivity and low cost of the lithium salt include that it can be done at room temperature and its yield compares relatively well with the conventional
Koenigs-Knorr
482:
DNA molecules contain 5-membered carbon rings called riboses that are directly attached to two phosphate groups and a nucleobase that contains amino groups. The nitrogen atoms from the amino group in the nucleotides are covalently linked to the
982:
Egleton, Richard D.; Bilsky, Edward J.; Tollin, Gordon; Dhanasekaran, Muthu; Lowery, John; Alves, Isabel; Davis, Peg; Porreca, Frank; Yamamura, Henry I. (2005-01-10). "Biousian glycopeptides penetrate the blood–brain barrier".
111:
Particularly in naturally occurring glycosides, the compound ROH from which the carbohydrate residue has been removed is often termed the aglycone, and the carbohydrate residue itself is sometimes referred to as the 'glycone'.
492:
are enzymes that catalyze the hydrolysis the N-glycosidic bond to free the damaged or modified nucleobase from the DNA, by cleaving the carbon-nitrogen glycosidic bond at the 2' carbon, subsequently initiating the
813:
De Winter K, Van
Renterghem L, Wuyts K, Pelantová H, Křen V, Soetaert W, Desmet T (2015). "Chemoenzymatic Synthesis of β-D Glucosides using Cellobiose Phosphorylase from Clostridium thermocellum".
187:
and is discouraged. All of these modified glycosidic bonds have different susceptibility to hydrolysis, and in the case of C-glycosyl structures, they are typically more resistant to hydrolysis.
508:
2 like mechanism. The stepwise function, the nucleobase acts as a leaving group before the anomeric carbon gets attacked by the water molecule, producing a short-lived unstable
442:
encourage B stereoselectivity through the gauche effect. This reasonable stereoselectivity is clear through visualization of the Felkin-Ahn models of the possible chair forms.
896:
Egleton RD, Mitchell SA, Huber JD, Janders J, Stropova D, Polt R, et al. (October 2000). "Improved bioavailability to the brain of glycosylated Met-enkephalin analogs".
1617:
336:
591:
421:(CP) toward synthesis of alpha-glycosides in ionic liquids. The best condition for use of CP was found to be in the presence of IL AMMOENG 101 and ethyl acetate.
333:
naturally-derived glucosidase. It is worth noting that Wen-Ya Lu utilized glucosidase in a reverse manner opposite to the enzyme's biological functionality:
445:
This method represents an encouraging way to selectivity incorporate B-ethyl, isopropyl and other glycosides with typical trichloroacetimidate chemistry.
1735:
1662:
1343:
1773:
203:
molecule showing how carbons are numbered. The terminal saccharide is linked via a β-1,6 glycosidic bond. The remaining linkages are all β-1,3.
762:
569:
1112:
264:, Nüchter et al. (2001) were able to achieve 100% yield of α- and β-D-glucosides. This method can be performed on a multi-kilogram scale.
1597:
1082:
461:
448:
1582:
389:
or sugar donors. Many biosynthetic pathways use mono- or oligosaccharides activated by a diphosphate linkage to lipids, such as
2543:
1406:
1433:
1394:
1384:
939:
Polt R, Dhanasekaran M, Keyari CM (September 2005). "Glycosylated neuropeptides: a new vista for neuropsychopharmacology?".
1389:
657:
Nüchter, Matthias; Ondruschka, Bernd; Lautenschläger, Werner (2001). "Microwave-Assisted
Synthesis of Alkyl Glycosides".
1336:
1766:
213:
When an anomeric center is involved in a glycosidic bond (as is common in nature) then one can distinguish between
1657:
1652:
221:
by the relative stereochemistry of the anomeric position and the stereocenter furthest from C1 in the saccharide.
2548:
1642:
1632:
1607:
1577:
1833:
1423:
1105:
418:
850:
2326:
1684:
1587:
1559:
1329:
276:
in the stereoselective synthesis of alkyl D-glucopyranosides via glycosylation, with the exception of using
1057:
Marco Brito-Arias, "Synthesis and
Characterization of Glycosides", second edition, Editorial Springer 2016.
2538:
2512:
2320:
1759:
382:
273:
2314:
1728:
1689:
378:
374:
249:
139:
via the formation of an N-glycosidic bond (shown as the vertical line between the N and the sugar cycle)
1723:
361:
in living organisms, they are typically first "activated" by being joined via a glycosidic bond to the
2453:
1647:
1538:
1401:
1360:
500:
Monofunctional glycosylases catalyze the hydrolysis of the N-glycosidic bond via either a stepwise, S
494:
325:
2533:
1549:
1413:
1379:
1098:
404:
394:
370:
97:
1713:
1468:
964:
921:
682:
517:
2 like mechanism, while most deoxyribonucleotides proceed through the stepwise like mechanism.
151:
that links the glycoside to the aglycone or reducing end sugar. In analogy, one also considers
1699:
1488:
1448:
1438:
1305:
1251:
1041:
956:
913:
871:
851:"Fluorine-Directed β-Galactosylation: Chemical Glycosylation Development by Molecular Editing"
830:
795:
758:
700:
Joshi VY, Sawant MR (2006). "A convenient stereoselective synthesis of β-D-glucopyranosides".
674:
639:
565:
285:
277:
1906:
1740:
1523:
1480:
1453:
1031:
1023:
992:
948:
905:
863:
822:
787:
732:
666:
631:
600:
386:
306:
301:
293:
2355:
2301:
2281:
2172:
1592:
1463:
489:
484:
233:
225:
73:
1718:
2342:
2139:
1896:
1873:
1853:
1627:
1428:
1036:
1011:
557:
93:
909:
2527:
2448:
2365:
2253:
2144:
1676:
1636:
1569:
1498:
1371:
1352:
1273:
1256:
357:
Before monosaccharide units are incorporated into glycoproteins, polysaccharides, or
261:
172:
968:
925:
686:
2332:
2213:
2195:
1843:
1783:
1622:
509:
72:. The reaction often favors formation of the α-glycosidic bond as shown due to the
43:
996:
753:
Lu WY, Lin GQ, Yu HL, Tong AM, Xu JH (2009-12-09). Whittall J, Sutton PW (eds.).
538:
46:(sugar) molecule to another group, which may or may not be another carbohydrate.
2490:
2478:
2350:
2261:
2009:
2004:
1944:
1708:
1458:
1261:
1218:
1208:
398:
297:
200:
62:
1517:
195:
2266:
2208:
2203:
2076:
2029:
1223:
1203:
736:
635:
366:
289:
229:
89:
81:
49:
39:
834:
678:
643:
604:
2424:
2420:
2375:
2289:
2271:
2238:
2223:
2044:
1967:
1929:
1443:
1418:
1310:
1293:
1288:
1283:
1278:
1268:
1246:
1213:
1195:
1121:
1075:
362:
253:
237:
124:
101:
85:
65:
1045:
960:
917:
875:
867:
826:
799:
791:
670:
313:
17:
2441:
2402:
2387:
2360:
2309:
2243:
2116:
2111:
2096:
2081:
1997:
1992:
1812:
1807:
1751:
1238:
1228:
397:, which transfer the sugar unit from the activated donor to an accepting
390:
168:
1067:
778:
Bucher C, Gilmour R (November 2010). "Fluorine-directed glycosylation".
280:
which is less expensive and toxic than the conventional method of using
2483:
2463:
2431:
2406:
2396:
2392:
2370:
2233:
2228:
2218:
2128:
2091:
2086:
2064:
2049:
2039:
1956:
1934:
1918:
1300:
1185:
1180:
1175:
1170:
1027:
136:
58:
54:
952:
457:
O-linked glycopeptides; pharmaceutical uses of O-glycosylated peptides
2473:
2468:
2458:
2435:
2412:
2380:
2167:
2162:
2106:
2069:
2054:
2034:
2021:
1982:
1977:
1972:
1885:
1838:
1828:
1802:
1797:
1162:
329:
281:
257:
208:
180:
160:
148:
132:
720:
619:
586:
120:
1529:
1012:"Mechanisms for enzymatic cleavage of the N-glycosidic bond in DNA"
848:
Durantie, Estelle; Bucher, Christoph; Gilmour, Ryan (16 May 2012).
2059:
1862:
1071:
460:
447:
393:. These activated donors are then substrates for enzymes known as
358:
335:
312:
194:
184:
69:
1321:
620:"Ueber die Verbindungen der Zucker mit den Alkoholen und Ketonen"
465:
Control of oxonium ion – Felkin-Ahn stereoselectivity chair forms
1755:
1325:
1094:
429:
Multiple chemical approaches exist to encourage selectivity of
385:(CMP). These activated biochemical intermediates are known as
159:), where the oxygen of the glycosidic bond is replaced with a
128:
1090:
171:. Substances containing N-glycosidic bonds are also known as
1087:
Cold Spring Harbor
Laboratory Press; 1999. Searchable online
721:"Ueber einige Derivate des Traubenzuckers und der Galactose"
143:
Glycosidic bonds of the form discussed above are known as
755:
Practical
Methods for Biocatalysis and Biotransformations
342:
560:. In Varki A, Cummings RD, Esko JD, et al. (eds.).
543:
Department of
Chemistry, Queen Mary University of London
1152:
1147:
1142:
1137:
488:
leading to the development of diseases such as cancer.
27:
Covalent bond joining a sugar molecule to another group
539:"Nomenclature of Carbohydrates (Recommendations 1996)"
228:
via glycosidic bonds in order to increase their water
564:(2nd ed.). Cold Spring Harbor Laboratory Press.
452:
Control of
Oxonium ion – Felkin-Ahn stereoselectivity
183:; the term "C-glycoside" is considered a misnomer by
2341:
2298:
2280:
2252:
2194:
2187:
2155:
2127:
2020:
1955:
1917:
1884:
1861:
1852:
1821:
1790:
1698:
1675:
1606:
1568:
1548:
1537:
1497:
1479:
1370:
1359:
1237:
1194:
1161:
1128:
305:attacks the carbon at the 5-position and through a
288:salts. D-glucose is first protected by forming the
248:Nüchter et al. (2001) have shown a new approach to
849:
191:Numbering, and α/β distinction of glycosidic bonds
92:(or a molecule derived from a saccharide) and the
167:, have the glycosidic bond oxygen replaced with
100:. A substance containing a glycosidic bond is a
179:bonds have the glycosidic oxygen replaced by a
725:Berichte der Deutschen Chemischen Gesellschaft
624:Berichte der Deutschen Chemischen Gesellschaft
592:Berichte der deutschen chemischen Gesellschaft
1767:
1337:
1106:
8:
757:. John Wiley & Sons. pp. 236–239.
2191:
1858:
1774:
1760:
1752:
1545:
1367:
1344:
1330:
1322:
1113:
1099:
1091:
1074:Compendium of Chemical Terminology, the "
1035:
224:Pharmacologists often join substances to
1736:Polyhedral skeletal electron pair theory
403:
240:have important physiological functions.
119:
80:A glycosidic bond is formed between the
48:
780:Angewandte Chemie International Edition
530:
558:"Structural Basis of Glycan Diversity"
7:
1016:Organic & Biomolecular Chemistry
1010:Drohat AC, Maiti A (November 2014).
748:
746:
504:1 like mechanism, or a concerted, S
815:Advanced Synthesis & Catalysis
587:"Ueber die Glucoside der Alkohole"
116:S-, N-, C-, and O-glycosidic bonds
25:
147:, in reference to the glycosidic
2508:
2507:
1528:
1522:
1516:
987:. Carbohydrate Science. Part 1.
272:Joshi et al. (2006) propose the
856:Chemistry – A European Journal
53:Formation of ethyl glucoside:
1:
910:10.1016/S0006-8993(00)02794-3
556:Bertozzi C, Rabuka D (2009).
997:10.1016/j.tetasy.2004.11.038
96:of some compound such as an
1084:Essentials of Glycobiology.
719:Koenigs W, Knorr E (1901).
702:Indian Journal of Chemistry
521:and a specific nucleobase.
417:et al. investigated use of
412:Disaccharide phosphorylases
2565:
1434:Metal–ligand multiple bond
941:Medicinal Research Reviews
562:Essentials of Glycobiology
401:(the acceptor substrate).
206:
131:, results from the sugar
2503:
1514:
737:10.1002/cber.190103401162
636:10.1002/cber.189502801248
478:N-Glycosidic bonds in DNA
1834:Cyclohexane conformation
1068:Definition of glycosides
659:Synthetic Communications
605:10.1002/cber.18930260327
419:cellobiose phosphorylase
260:in a rotor reactor with
2327:Isomaltooligosaccharide
1284:Anthraquinone glycoside
425:Directed glycosylations
328:(or glycosidases), are
300:, and then addition of
268:Vishal Y Joshi's method
163:atom. In the same way,
2544:Carbohydrate chemistry
2321:Galactooligosaccharide
985:Tetrahedron: Asymmetry
868:10.1002/chem.201200468
827:10.1002/adsc.201500077
792:10.1002/anie.201004467
618:Fischer, Emil (1895).
585:Fischer, Emil (1893).
466:
453:
408:
383:cytidine monophosphate
349:
317:
274:Koenigs-Knorr reaction
267:
204:
140:
77:
2315:Fructooligosaccharide
671:10.1081/scc-100104035
464:
451:
407:
379:thymidine diphosphate
375:guanosine diphosphate
339:
316:
250:Fischer glycosidation
198:
123:
52:
1424:Coordinate (dipolar)
1269:Cyanogenic glycoside
495:base excision repair
395:glycosyltransferases
353:Glycosyltransferases
326:Glycoside hydrolases
321:Glycoside hydrolases
1598:C–H···O interaction
1380:Electron deficiency
1294:Flavonoid glycoside
1247:Alcoholic glycoside
435:β-glycosidic bonds.
371:uridine diphosphate
258:refluxing apparatus
256:oven equipped with
244:Chemical approaches
232:; this is known as
1583:Resonance-assisted
1289:Coumarin glycoside
1279:Phenolic glycoside
1028:10.1039/c4ob01063a
467:
454:
409:
350:
340:Lu, Wen-Ya et al.
318:
219:β-glycosidic bonds
205:
165:N-glycosidic bonds
153:S-glycosidic bonds
145:O-glycosidic bonds
141:
78:
36:glycosidic linkage
2521:
2520:
2499:
2498:
2183:
2182:
1749:
1748:
1700:Electron counting
1671:
1670:
1560:London dispersion
1512:
1511:
1489:Metal aromaticity
1319:
1318:
1306:Steviol glycoside
1252:Cardiac glycoside
1153:C-glycosidic bond
1148:S-glycosidic bond
1143:N-glycosidic bond
1138:O-glycosidic bond
1022:(42): 8367–8378.
953:10.1002/med.20039
862:(26): 8208–8215.
764:978-0-470-74859-6
571:978-0-87969-770-9
387:sugar nucleotides
278:lithium carbonate
127:, a component of
16:(Redirected from
2556:
2549:Chemical bonding
2511:
2510:
2302:oligosaccharides
2282:Tetrasaccharides
2192:
1907:Dihydroxyacetone
1859:
1776:
1769:
1762:
1753:
1741:Jemmis mno rules
1593:Dihydrogen bonds
1546:
1532:
1526:
1520:
1454:Hyperconjugation
1368:
1346:
1339:
1332:
1323:
1115:
1108:
1101:
1092:
1050:
1049:
1039:
1007:
1001:
1000:
979:
973:
972:
936:
930:
929:
893:
887:
886:
884:
882:
853:
845:
839:
838:
821:(8): 1961–1969.
810:
804:
803:
775:
769:
768:
750:
741:
740:
716:
710:
709:
697:
691:
690:
665:(9): 1277–1283.
654:
648:
647:
630:(1): 1145–1167.
615:
609:
608:
599:(3): 2400–2412.
582:
576:
575:
553:
547:
546:
535:
490:DNA glycosylases
307:transition state
302:hydrogen bromide
294:acetic anhydride
61:combine to form
21:
2564:
2563:
2559:
2558:
2557:
2555:
2554:
2553:
2524:
2523:
2522:
2517:
2495:
2356:Oat beta-glucan
2343:Polysaccharides
2337:
2300:
2294:
2276:
2248:
2179:
2173:Neuraminic acid
2151:
2123:
2016:
1951:
1913:
1880:
1854:Monosaccharides
1848:
1817:
1786:
1780:
1750:
1745:
1694:
1667:
1610:
1602:
1564:
1551:
1541:
1533:
1527:
1521:
1508:
1493:
1475:
1363:
1355:
1350:
1320:
1315:
1233:
1190:
1157:
1124:
1119:
1081:Varki A et al.
1064:
1054:
1053:
1009:
1008:
1004:
981:
980:
976:
938:
937:
933:
895:
894:
890:
880:
878:
847:
846:
842:
812:
811:
807:
777:
776:
772:
765:
752:
751:
744:
718:
717:
713:
699:
698:
694:
656:
655:
651:
617:
616:
612:
584:
583:
579:
572:
555:
554:
550:
537:
536:
532:
527:
516:
507:
503:
497:(BER) pathway.
480:
459:
427:
414:
355:
323:
292:by addition of
270:
246:
234:glucuronidation
226:glucuronic acid
211:
193:
118:
74:anomeric effect
32:glycosidic bond
28:
23:
22:
15:
12:
11:
5:
2562:
2560:
2552:
2551:
2546:
2541:
2536:
2526:
2525:
2519:
2518:
2516:
2515:
2504:
2501:
2500:
2497:
2496:
2494:
2493:
2488:
2487:
2486:
2481:
2471:
2466:
2461:
2456:
2454:Levan beta 2→6
2451:
2446:
2445:
2444:
2428:
2417:
2416:
2415:
2399:
2390:
2385:
2384:
2383:
2378:
2373:
2368:
2363:
2358:
2347:
2345:
2339:
2338:
2336:
2335:
2330:
2324:
2318:
2312:
2306:
2304:
2296:
2295:
2293:
2292:
2286:
2284:
2278:
2277:
2275:
2274:
2269:
2264:
2258:
2256:
2254:Trisaccharides
2250:
2249:
2247:
2246:
2241:
2236:
2231:
2226:
2221:
2216:
2211:
2206:
2200:
2198:
2189:
2185:
2184:
2181:
2180:
2178:
2177:
2176:
2175:
2165:
2159:
2157:
2153:
2152:
2150:
2149:
2148:
2147:
2142:
2140:Mannoheptulose
2133:
2131:
2125:
2124:
2122:
2121:
2120:
2119:
2114:
2109:
2101:
2100:
2099:
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1900:
1899:
1897:Glyceraldehyde
1890:
1888:
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1879:
1878:
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1874:Glycolaldehyde
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1063:
1062:External links
1060:
1059:
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1052:
1051:
1002:
974:
947:(5): 557–585.
931:
898:Brain Research
888:
840:
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786:(46): 8724–8.
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763:
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731:(1): 957–981.
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262:pressure bombs
252:. Employing a
245:
242:
207:Main article:
192:
189:
173:glycosylamines
157:thioglycosides
117:
114:
94:hydroxyl group
26:
24:
14:
13:
10:
9:
6:
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3:
2:
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2539:Carbohydrates
2537:
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2449:Hemicellulose
2447:
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2197:
2196:Disaccharides
2193:
2190:
2186:
2174:
2171:
2170:
2169:
2166:
2164:
2161:
2160:
2158:
2154:
2146:
2145:Sedoheptulose
2143:
2141:
2138:
2137:
2136:Ketoheptoses
2135:
2134:
2132:
2130:
2126:
2118:
2115:
2113:
2110:
2108:
2105:
2104:
2103:Deoxy sugars
2102:
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2019:
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1991:
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1989:Ketopentoses
1988:
1984:
1981:
1979:
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1966:
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1964:Aldopentoses
1963:
1962:
1960:
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1928:
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1926:Aldotetroses
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1784:carbohydrates
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1715:
1714:Hückel's rule
1712:
1711:
1710:
1707:
1706:
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1677:Bond cleavage
1674:
1664:
1661:
1659:
1656:
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1651:
1649:
1646:
1644:
1643:Intercalation
1641:
1638:
1634:
1633:Metallophilic
1631:
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1550:Van der Waals
1547:
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1324:
1312:
1311:Thioglycoside
1309:
1307:
1304:
1302:
1299:
1295:
1292:
1290:
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1280:
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1274:Glycosylamine
1272:
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1267:
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1257:Bufadienolide
1255:
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1199:
1197:
1193:
1187:
1186:1,6-Glycoside
1184:
1182:
1181:1,4-Glycoside
1179:
1177:
1174:
1172:
1169:
1168:
1166:
1164:
1160:
1154:
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1149:
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749:
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243:
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239:
236:. Many other
235:
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99:
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87:
83:
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71:
67:
64:
60:
56:
51:
47:
45:
42:that joins a
41:
38:is a type of
37:
33:
19:
2430:
2419:
2401:
2333:Maltodextrin
2214:Isomaltulose
2005:Deoxy sugars
1941:Ketotetrose
1844:Mutarotation
1719:Baird's rule
1439:Charge-shift
1402:Hypervalence
1129:
1083:
1019:
1015:
1005:
991:(1): 65–75.
988:
984:
977:
944:
940:
934:
904:(1): 37–46.
901:
897:
891:
879:. Retrieved
859:
855:
843:
818:
814:
808:
783:
779:
773:
754:
728:
724:
714:
705:
701:
695:
662:
658:
652:
627:
623:
613:
596:
590:
580:
561:
551:
542:
533:
519:
510:oxacarbenium
499:
481:
472:
468:
444:
440:
434:
430:
428:
415:
356:
345:
341:
324:
271:
247:
223:
218:
214:
212:
176:
164:
156:
155:(which form
152:
144:
142:
110:
106:
79:
44:carbohydrate
35:
31:
29:
2491:Xanthan gum
2479:Amylopectin
2351:Beta-glucan
2262:Maltotriose
2077:Ketohexoses
2030:Aldohexoses
2010:Deoxyribose
1945:Erythrulose
1903:Ketotriose
1893:Aldotriose
1709:Aromaticity
1685:Heterolysis
1663:Salt bridge
1608:Noncovalent
1578:Low-barrier
1459:Aromaticity
1449:Conjugation
1429:Pi backbond
1262:Cardenolide
1219:Glucuronide
1209:Galactoside
1176:β-Glycoside
1171:α-Glycoside
1070:, from the
399:nucleophile
365:group of a
298:acetic acid
88:group of a
2534:Glycosides
2528:Categories
2267:Melezitose
2209:Isomaltose
2204:Cellobiose
1870:Aldodiose
1637:aurophilic
1618:Mechanical
1224:Rhamnoside
1204:Fructoside
1122:Glycosides
708:: 461–465.
525:References
381:(TDP), or
367:nucleotide
348:, 236–239.
290:peracetate
238:glycosides
230:solubility
177:C-glycosyl
90:saccharide
82:hemiacetal
40:ether bond
18:Glycosidic
2421:Galactose
2376:Cellulose
2366:Sizofiran
2290:Stachyose
2272:Raffinose
2239:Trehalose
2224:Lactulose
2045:Galactose
1968:Arabinose
1930:Erythrose
1782:Types of
1729:spherical
1690:Homolysis
1653:Cation–pi
1628:Chalcogen
1588:Symmetric
1444:Hapticity
1214:Glucoside
1076:Gold Book
835:1615-4150
679:0039-7911
644:1099-0682
363:phosphate
254:microwave
125:Adenosine
102:glycoside
86:hemiketal
66:glucoside
2513:Category
2442:Glycogen
2425:Galactan
2403:Fructose
2388:Chitosan
2361:Lentinan
2310:Acarbose
2244:Turanose
2188:Multiple
2129:Heptoses
2117:Rhamnose
2112:Fuculose
2097:Tagatose
2082:Fructose
1998:Xylulose
1993:Ribulose
1957:Pentoses
1919:Tetroses
1822:Geometry
1813:Pyranose
1808:Furanose
1658:Anion–pi
1648:Stacking
1570:Hydrogen
1481:Metallic
1372:Covalent
1364:(strong)
1239:Aglycone
1229:Riboside
1163:Geometry
1046:25181003
969:38798797
961:16075406
926:18102579
918:11033091
881:24 April
876:22592962
800:20886497
687:93986043
485:anomeric
391:dolichol
369:such as
199:A β-1,6
169:nitrogen
2484:Amylose
2432:Glucose
2407:Fructan
2397:Dextran
2393:Dextrin
2371:Zymosan
2234:Sucrose
2229:Maltose
2219:Lactose
2168:Nonoses
2163:Octoses
2156:Above 7
2092:Sorbose
2087:Psicose
2065:Mannose
2050:Glucose
2040:Altrose
2022:Hexoses
1935:Threose
1886:Trioses
1791:General
1623:Halogen
1469:bicyclo
1414:Agostic
1301:Saponin
1196:Glycone
1037:4238931
377:(GDP),
373:(UDP),
330:enzymes
310:method.
286:mercury
137:adenine
98:alcohol
59:ethanol
55:Glucose
2474:Starch
2469:Pectin
2464:Mannan
2459:Lignin
2436:Glucan
2413:Inulin
2381:Chitin
2107:Fucose
2070:Talose
2055:Gulose
2035:Allose
1983:Xylose
1978:Ribose
1973:Lyxose
1863:Dioses
1839:Epimer
1829:Anomer
1803:Ketose
1798:Aldose
1724:Möbius
1552:forces
1542:(weak)
1044:
1034:
967:
959:
924:
916:
874:
833:
798:
761:
685:
677:
642:
568:
359:lipids
282:silver
209:Anomer
201:glucan
181:carbon
161:sulfur
149:oxygen
133:ribose
2329:(IMO)
2323:(GOS)
2317:(FOS)
2299:Other
2060:Idose
1702:rules
1611:other
1499:Ionic
1407:3c–4e
1395:8c–2e
1390:4c–2e
1385:3c–2e
1072:IUPAC
965:S2CID
922:S2CID
683:S2CID
185:IUPAC
70:water
63:ethyl
1464:homo
1419:Bent
1130:Bond
1042:PMID
957:PMID
914:PMID
883:2022
872:PMID
831:ISSN
796:PMID
759:ISBN
675:ISSN
640:ISSN
566:ISBN
433:and
346:2010
217:and
135:and
68:and
57:and
1032:PMC
1024:doi
993:doi
949:doi
906:doi
902:881
864:doi
823:doi
819:357
788:doi
733:doi
706:45B
667:doi
632:doi
601:doi
296:in
284:or
129:RNA
84:or
34:or
2530::
2434:/
2423:/
2405:/
2395:/
1040:.
1030:.
1020:12
1018:.
1014:.
989:16
963:.
955:.
945:25
943:.
920:.
912:.
900:.
870:.
860:18
858:.
854:.
829:.
817:.
794:.
784:49
782:.
745:^
729:34
727:.
723:.
704:.
681:.
673:.
663:31
661:.
638:.
628:28
626:.
622:.
597:26
595:.
589:.
541:.
431:α-
344:.
215:α-
175:.
104:.
30:A
1775:e
1768:t
1761:v
1639:)
1635:(
1345:e
1338:t
1331:v
1114:e
1107:t
1100:v
1078:"
1048:.
1026::
999:.
995::
971:.
951::
928:.
908::
885:.
866::
837:.
825::
802:.
790::
767:.
739:.
735::
689:.
669::
646:.
634::
607:.
603::
574:.
545:.
515:N
506:N
502:N
76:.
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
