33:
305:
454:
24:
1483:
421:
145:
581:. The amino group bears either an acetyl or a glycolyl group. The hydroxyl substituents may vary considerably: acetyl, lactyl, methyl, sulfate and phosphate groups have been found.
584:
The name "neuraminic acid" was introduced by German scientist E. Klenk in 1941, in reference to the brain lipids from which it was derived as a cleavage product.
434:
554:
Neuraminic acid does not occur naturally, but many of its derivatives are found widely distributed in animal tissues and in bacteria, especially in
595:, and the residue is typically found with additional chemical modifications in biological systems. As a family, these residues are known as
354:
747:
695:
328:
InChI=1S/C9H17NO8/c10-5-3(12)1-9(17,8(15)16)18-7(5)6(14)4(13)2-11/h3-7,11-14,17H,1-2,10H2,(H,15,16)/t3-,4+,5+,6+,7+,9-/m0/s1
429:
338:
InChI=1/C9H17NO8/c10-5-3(12)1-9(17,8(15)16)18-7(5)6(14)4(13)2-11/h3-7,11-14,17H,1-2,10H2,(H,15,16)/t3-,4+,5+,6+,7+,9-/m0/s1
1512:
527:
at position 3 is deoxidised (oxygen is removed from it), and the hydroxyl group at position 5 is substituted with an
319:
441:
229:
32:
503:. Although 9-carbon sugars do not occur naturally, neuraminic acid may be regarded as a theoretical 9-carbon
71:
512:
262:
192:
740:
283:
185:
675:
648:
300:
807:
223:
1300:
640:
575:
1486:
1294:
733:
1507:
1288:
45:
614:
viruses have a neuraminidase enzyme, signified in the name "H#N#", where the H refers to an
212:
1517:
1427:
271:
8:
623:
304:
121:
111:
674:
Blanco, Antonio; Blanco, Gustavo (2017-01-01), Blanco, Antonio; Blanco, Gustavo (eds.),
165:
687:
536:
691:
492:
457:
880:
683:
377:
251:
1329:
1275:
1255:
1316:
1113:
870:
847:
827:
524:
520:
412:
453:
1501:
1422:
1339:
1227:
1118:
619:
607:
1306:
1187:
1169:
817:
757:
715:
Klenk, E. 1941. Neuraminsäure, das
Spaltprodukt eines neuen Gehirnlipoids.
606:
Among their many biological functions, these structures are substrates for
596:
555:
540:
1464:
1452:
1324:
1235:
983:
978:
918:
725:
635:
571:
559:
548:
528:
500:
496:
1240:
1182:
1177:
1050:
1003:
488:
461:
400:
203:
23:
570:-substituted derivatives of neuraminic acid are collectively known as
1398:
1394:
1349:
1263:
1245:
1212:
1197:
1018:
941:
903:
516:
411:
Except where otherwise noted, data are given for materials in their
1415:
1376:
1361:
1334:
1283:
1217:
1090:
1085:
1070:
1055:
971:
966:
786:
781:
603:-acetylneuraminic acid, Neu5Ac, is typical in human glycoproteins.
144:
1457:
1437:
1405:
1380:
1370:
1366:
1344:
1207:
1202:
1192:
1102:
1065:
1060:
1038:
1023:
1013:
930:
908:
892:
615:
238:
1447:
1442:
1432:
1409:
1386:
1354:
1141:
1136:
1080:
1043:
1028:
1008:
995:
956:
951:
946:
859:
812:
802:
776:
771:
535:). Neuraminic acid may also be visualized as the product of an
504:
176:
1033:
836:
588:
156:
134:
288:
611:
610:
enzymes which cleave neuraminic acid residues. Human
1499:
574:, the predominant form in mammalian cells being
250:
120:
741:
507:in which the first link of the chain (the –CH
673:
755:
748:
734:
303:
211:
270:
452:
299:
228:
1500:
729:
331:Key: CERZMXAJYMMUDR-YOQZMRDMSA-N
191:
184:
164:
669:
667:
591:symbol used for neuraminic acid is
341:Key: CERZMXAJYMMUDR-YOQZMRDMBH
241:
13:
688:10.1016/b978-0-12-803550-4.00004-5
682:, Academic Press, pp. 73–97,
14:
1529:
664:
1482:
1481:
419:
31:
22:
499:with a backbone formed by nine
415:(at 25 °C , 100 kPa).
98:pentahydroxy-2-oxononanoic acid
709:
622:and N refers to an isoform of
458:Two-dimensional representation
1:
657:
362:O=C(O)1(O)O((O)(O)CO)(N)(O)C1
551:(2-amino-2-deoxy-mannose).
487:-non-2-ulosonic acid) is an
7:
717:Zeitschr. f. Physiol. Chem.
676:"Chapter 4 - Carbohydrates"
629:
405:267.233 g/mol
10:
1534:
1513:Monosaccharide derivatives
460:of neuraminic acid in its
1477:
1315:
1272:
1254:
1226:
1168:
1161:
1129:
1101:
994:
929:
891:
858:
835:
826:
795:
764:
409:
370:
350:
315:
104:
70:
44:
39:
30:
21:
808:Cyclohexane conformation
652:-Glycolylneuraminic acid
1301:Isomaltooligosaccharide
1295:Galactooligosaccharide
644:-Acetylneuraminic acid
579:-acetylneuraminic acid
465:
1289:Fructooligosaccharide
471:(5-amino-3,5-dideoxy-
456:
72:Systematic IUPAC name
680:Medical Biochemistry
96:)-5-Amino-4,6,7,8,9-
65:-non-2-ulosonic acid
49:5-Amino-3,5-dideoxy-
624:viral neuraminidase
18:
537:aldol-condensation
466:
442:Infobox references
16:
1495:
1494:
1473:
1472:
1157:
1156:
697:978-0-12-803550-4
546:
482:
474:
450:Chemical compound
448:
447:
284:CompTox Dashboard
146:Interactive image
1525:
1485:
1484:
1276:oligosaccharides
1256:Tetrasaccharides
1166:
1165:
881:Dihydroxyacetone
833:
832:
750:
743:
736:
727:
726:
720:
719:1941; 268:50-58.
713:
707:
706:
705:
704:
671:
544:
523:(–C(=O)OH), the
497:amino sugar
480:
472:
432:
426:
423:
422:
378:Chemical formula
308:
307:
292:
290:
274:
254:
243:
232:
230:Neuraminic+Acids
215:
195:
188:
168:
148:
124:
97:
60:
52:
35:
26:
19:
17:Neuraminic acid
15:
1533:
1532:
1528:
1527:
1526:
1524:
1523:
1522:
1498:
1497:
1496:
1491:
1469:
1330:Oat beta-glucan
1317:Polysaccharides
1311:
1274:
1268:
1250:
1222:
1153:
1147:Neuraminic acid
1125:
1097:
990:
925:
887:
854:
828:Monosaccharides
822:
791:
760:
754:
724:
723:
714:
710:
702:
700:
698:
672:
665:
660:
632:
599:. For example,
534:
510:
491:(in particular
469:Neuraminic acid
451:
444:
439:
438:
437: ?)
428:
424:
420:
416:
394:
390:
386:
380:
366:
363:
358:
357:
346:
343:
342:
339:
333:
332:
329:
323:
322:
311:
301:DTXSID401316250
293:
286:
277:
257:
244:
218:
198:
171:
151:
138:
127:
114:
100:
99:
66:
58:
50:
12:
11:
5:
1531:
1521:
1520:
1515:
1510:
1493:
1492:
1490:
1489:
1478:
1475:
1474:
1471:
1470:
1468:
1467:
1462:
1461:
1460:
1455:
1445:
1440:
1435:
1430:
1428:Levan beta 2→6
1425:
1420:
1419:
1418:
1402:
1391:
1390:
1389:
1373:
1364:
1359:
1358:
1357:
1352:
1347:
1342:
1337:
1332:
1321:
1319:
1313:
1312:
1310:
1309:
1304:
1298:
1292:
1286:
1280:
1278:
1270:
1269:
1267:
1266:
1260:
1258:
1252:
1251:
1249:
1248:
1243:
1238:
1232:
1230:
1228:Trisaccharides
1224:
1223:
1221:
1220:
1215:
1210:
1205:
1200:
1195:
1190:
1185:
1180:
1174:
1172:
1163:
1159:
1158:
1155:
1154:
1152:
1151:
1150:
1149:
1139:
1133:
1131:
1127:
1126:
1124:
1123:
1122:
1121:
1116:
1114:Mannoheptulose
1107:
1105:
1099:
1098:
1096:
1095:
1094:
1093:
1088:
1083:
1075:
1074:
1073:
1068:
1063:
1058:
1048:
1047:
1046:
1041:
1036:
1031:
1026:
1021:
1016:
1011:
1000:
998:
992:
991:
989:
988:
987:
986:
976:
975:
974:
969:
961:
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959:
954:
949:
944:
935:
933:
927:
926:
924:
923:
922:
921:
913:
912:
911:
906:
897:
895:
889:
888:
886:
885:
884:
883:
875:
874:
873:
871:Glyceraldehyde
864:
862:
856:
855:
853:
852:
851:
850:
848:Glycolaldehyde
841:
839:
830:
824:
823:
821:
820:
815:
810:
805:
799:
797:
793:
792:
790:
789:
784:
779:
774:
768:
766:
762:
761:
753:
752:
745:
738:
730:
722:
721:
708:
696:
662:
661:
659:
656:
655:
654:
646:
638:
631:
628:
532:
525:hydroxyl group
521:carboxyl group
508:
462:straight chain
449:
446:
445:
440:
418:
417:
413:standard state
410:
407:
406:
403:
397:
396:
392:
388:
384:
381:
376:
373:
372:
368:
367:
365:
364:
361:
353:
352:
351:
348:
347:
345:
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330:
327:
326:
318:
317:
316:
313:
312:
310:
309:
296:
294:
282:
279:
278:
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267:
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259:
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226:
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132:
129:
128:
126:
125:
117:
115:
110:
107:
106:
102:
101:
75:
74:
68:
67:
48:
42:
41:
37:
36:
28:
27:
9:
6:
4:
3:
2:
1530:
1519:
1516:
1514:
1511:
1509:
1506:
1505:
1503:
1488:
1480:
1479:
1476:
1466:
1463:
1459:
1456:
1454:
1451:
1450:
1449:
1446:
1444:
1441:
1439:
1436:
1434:
1431:
1429:
1426:
1424:
1423:Hemicellulose
1421:
1417:
1414:
1413:
1412:
1411:
1407:
1403:
1401:
1400:
1396:
1392:
1388:
1385:
1384:
1383:
1382:
1378:
1374:
1372:
1368:
1365:
1363:
1360:
1356:
1353:
1351:
1348:
1346:
1343:
1341:
1338:
1336:
1333:
1331:
1328:
1327:
1326:
1323:
1322:
1320:
1318:
1314:
1308:
1305:
1302:
1299:
1296:
1293:
1290:
1287:
1285:
1282:
1281:
1279:
1277:
1271:
1265:
1262:
1261:
1259:
1257:
1253:
1247:
1244:
1242:
1239:
1237:
1234:
1233:
1231:
1229:
1225:
1219:
1216:
1214:
1211:
1209:
1206:
1204:
1201:
1199:
1196:
1194:
1191:
1189:
1186:
1184:
1181:
1179:
1176:
1175:
1173:
1171:
1170:Disaccharides
1167:
1164:
1160:
1148:
1145:
1144:
1143:
1140:
1138:
1135:
1134:
1132:
1128:
1120:
1119:Sedoheptulose
1117:
1115:
1112:
1111:
1110:Ketoheptoses
1109:
1108:
1106:
1104:
1100:
1092:
1089:
1087:
1084:
1082:
1079:
1078:
1077:Deoxy sugars
1076:
1072:
1069:
1067:
1064:
1062:
1059:
1057:
1054:
1053:
1052:
1049:
1045:
1042:
1040:
1037:
1035:
1032:
1030:
1027:
1025:
1022:
1020:
1017:
1015:
1012:
1010:
1007:
1006:
1005:
1002:
1001:
999:
997:
993:
985:
982:
981:
980:
977:
973:
970:
968:
965:
964:
963:Ketopentoses
962:
958:
955:
953:
950:
948:
945:
943:
940:
939:
938:Aldopentoses
937:
936:
934:
932:
928:
920:
917:
916:
914:
910:
907:
905:
902:
901:
900:Aldotetroses
899:
898:
896:
894:
890:
882:
879:
878:
876:
872:
869:
868:
866:
865:
863:
861:
857:
849:
846:
845:
843:
842:
840:
838:
834:
831:
829:
825:
819:
816:
814:
811:
809:
806:
804:
801:
800:
798:
794:
788:
785:
783:
780:
778:
775:
773:
770:
769:
767:
763:
759:
758:carbohydrates
751:
746:
744:
739:
737:
732:
731:
728:
718:
712:
699:
693:
689:
685:
681:
677:
670:
668:
663:
653:
651:
647:
645:
643:
639:
637:
634:
633:
627:
625:
621:
620:hemagglutinin
617:
613:
609:
608:neuraminidase
604:
602:
598:
594:
590:
585:
582:
580:
578:
573:
569:
565:
561:
557:
556:glycoproteins
552:
550:
542:
538:
530:
526:
522:
518:
514:
506:
502:
498:
494:
490:
486:
478:
470:
463:
459:
455:
443:
436:
431:
414:
408:
404:
402:
399:
398:
382:
379:
375:
374:
369:
360:
359:
356:
349:
335:
325:
324:
321:
314:
306:
302:
298:
297:
295:
285:
281:
280:
273:
269:
268:
266:
264:
261:
260:
253:
249:
248:
246:
240:
236:
235:
231:
227:
225:
222:
221:
214:
210:
209:
207:
205:
202:
201:
194:
193:ChEMBL1234621
190:
187:
183:
182:
180:
178:
175:
174:
167:
163:
162:
160:
158:
155:
154:
147:
143:
142:
140:
136:
131:
130:
123:
119:
118:
116:
113:
109:
108:
103:
95:
91:
87:
83:
79:
73:
69:
64:
56:
47:
43:
38:
34:
29:
25:
20:
1508:Amino sugars
1404:
1393:
1375:
1307:Maltodextrin
1188:Isomaltulose
1146:
979:Deoxy sugars
915:Ketotetrose
818:Mutarotation
716:
711:
701:, retrieved
679:
649:
641:
605:
600:
597:sialic acids
592:
586:
583:
576:
572:sialic acids
567:
563:
560:gangliosides
553:
541:pyruvic acid
501:carbon atoms
484:
476:
468:
467:
186:ChEMBL165084
105:Identifiers
93:
89:
85:
81:
77:
62:
54:
1518:Sugar acids
1465:Xanthan gum
1453:Amylopectin
1325:Beta-glucan
1236:Maltotriose
1051:Ketohexoses
1004:Aldohexoses
984:Deoxyribose
919:Erythrulose
877:Ketotriose
867:Aldotriose
636:Sialic acid
549:mannosamine
529:amino group
371:Properties
166:CHEBI:49022
1502:Categories
1241:Melezitose
1183:Isomaltose
1178:Cellobiose
844:Aldodiose
703:2020-12-16
658:References
513:position 1
401:Molar mass
272:L4866H38XY
204:ChemSpider
133:3D model (
112:CAS Number
46:IUPAC name
1395:Galactose
1350:Cellulose
1340:Sizofiran
1264:Stachyose
1246:Raffinose
1213:Trehalose
1198:Lactulose
1019:Galactose
942:Arabinose
904:Erythrose
756:Types of
1487:Category
1416:Glycogen
1399:Galactan
1377:Fructose
1362:Chitosan
1335:Lentinan
1284:Acarbose
1218:Turanose
1162:Multiple
1103:Heptoses
1091:Rhamnose
1086:Fuculose
1071:Tagatose
1056:Fructose
972:Xylulose
967:Ribulose
931:Pentoses
893:Tetroses
796:Geometry
787:Pyranose
782:Furanose
630:See also
517:oxidised
493:ulosonic
122:114-04-5
1458:Amylose
1406:Glucose
1381:Fructan
1371:Dextran
1367:Dextrin
1345:Zymosan
1208:Sucrose
1203:Maltose
1193:Lactose
1142:Nonoses
1137:Octoses
1130:Above 7
1066:Sorbose
1061:Psicose
1039:Mannose
1024:Glucose
1014:Altrose
996:Hexoses
909:Threose
860:Trioses
765:General
616:isoform
519:into a
485:galacto
477:glycero
435:what is
433: (
395:
239:PubChem
63:galacto
55:glycero
1448:Starch
1443:Pectin
1438:Mannan
1433:Lignin
1410:Glucan
1387:Inulin
1355:Chitin
1081:Fucose
1044:Talose
1029:Gulose
1009:Allose
957:Xylose
952:Ribose
947:Lyxose
837:Dioses
813:Epimer
803:Anomer
777:Ketose
772:Aldose
694:
562:. The
511:OH at
505:ketose
489:acidic
430:verify
427:
355:SMILES
252:513472
213:447972
177:ChEMBL
40:Names
1303:(IMO)
1297:(GOS)
1291:(FOS)
1273:Other
1034:Idose
589:IUPAC
566:- or
515:) is
464:form.
320:InChI
157:ChEBI
135:JSmol
692:ISBN
587:The
558:and
543:and
531:(–NH
263:UNII
224:MeSH
684:doi
618:of
612:flu
593:Neu
539:of
289:EPA
242:CID
1504::
1408:/
1397:/
1379:/
1369:/
690:,
678:,
666:^
626:.
495:)
391:NO
389:17
92:,8
88:,7
84:,6
80:,5
76:(4
749:e
742:t
735:v
686::
650:N
642:N
601:N
577:N
568:O
564:N
547:-
545:D
533:2
509:2
483:-
481:D
479:-
475:-
473:D
425:N
393:8
387:H
385:9
383:C
291:)
287:(
137:)
94:R
90:S
86:R
82:R
78:S
61:-
59:d
57:-
53:-
51:d
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