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N-Acetylneuraminic acid

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Neu5Ac is also important in the biology of a number of pathogenic and symbiotic bacteria as it can be used either as a nutrient, providing both carbon and nitrogen to the bacteria, or in some pathogens, can be activated and placed on the cell surface. Bacteria have evolved transporters for Neu5Ac to
997: 139: 990: 983: 867:"Sialic acid transport in Haemophilus influenzae is essential for lipopolysaccharide sialylation and serum resistance and is dependent on a novel tripartite ATP-independent periplasmic transporter" 451: 495: 594: 360: 334:
InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11+/m0/s1
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InChI=1/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11+/m0/s1
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enable them to capture it from their environment and a number of these have been characterized including the NanT protein from
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Severi E, Randle G, Kivlin P, Whitfield K, Young R, Moxon R, Kelly D, Hood D, Thomas GH (2005).
964:""ACENOBEL® Sustained Release Tablet 500 mg" Approved for Distal Myopathy with Rimmed Vacuoles" 945: 888: 847: 798: 749: 731: 692: 935: 927: 878: 837: 829: 818:"Identification of an inducible catabolic system for sialic acids (nan) in Escherichia coli" 788: 780: 739: 723: 682: 589: 383: 179: 277: 1208: 634: 604: 567: 710:
Vimr, Eric R.; Kalivoda, Kathryn A.; Deszo, Eric L.; Steenbergen, Susan M. (March 2004).
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In Japan, Neu5Ac is approved under the trade name Acenobel for the treatment of
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This residue is negatively charged at physiological pH and is found in complex
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found in human cells, and many mammalian cells. Other forms, such as
570:—mouth, nose, GI, respiratory tract), Neu5Ac acts as a receptor for 472:
Except where otherwise noted, data are given for materials in their
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Vimr ER, Kalivoda KA, Deszo EL, Steenbergen SM (2004).
578:(an early step in acquiring influenzavirus infection). 490: 1181: 1163: 1140: 1097: 1074: 1038: 1019: 914:Post DM, Mungur R, Gibson BW, Munson RS Jr (2005). 440:186 °C (367 °F; 459 K) (decomposes) 574:viruses, allowing attachment to mucous cells via 562:Along with involvement in preventing infections ( 671:"Sialic acid utilization by bacterial pathogens" 256: 769:"Diversity of microbial sialic acid metabolism" 712:"Diversity of Microbial Sialic Acid Metabolism" 114: 991: 8: 664: 662: 998: 984: 976: 716:Microbiology and Molecular Biology Reviews 309: 200: 178: 26: 939: 882: 841: 792: 743: 686: 276: 658: 365: 330: 305: 234: 191: 669:Severi E, Hood DW, Thomas GH (2007). 582:In the biology of bacterial pathogens 337:Key: SQVRNKJHWKZAKO-YRMXFSIDSA-N 158: 7: 623:distal myopathy with rimmed vacuoles 461: 368:OC(=O)1(O)C(O)(NC(C)=O)(O1)(O)(O)CO 347:Key: SQVRNKJHWKZAKO-YRMXFSIDBI 247: 217: 25: 1006:Other drugs for disorders of the 932:10.1128/IAI.73.10.6727-6735.2005 884:10.1111/j.1365-2958.2005.04901.x 480: 401: 395: 36: 547:and glycoproteins found at the 476:(at 25 °C , 100 kPa). 1165:Histone deacetylase inhibitors 785:10.1128/mmbr.68.1.132-153.2004 728:10.1128/MMBR.68.1.132-153.2004 404: 389: 1: 834:10.1128/jb.164.2.845-853.1985 1084:Delandistrogene moxeparvovec 54:5-(Acetylamino)-3,5-dideoxy- 688:10.1099/mic.0.2007/009480-0 536:, may also occur in cells. 1303: 1099:Antisense oligonucleotides 70:-non-2-ulopyranosonic acid 1227: 816:Vimr ER, Troy FA (1985). 534:N-Glycolylneuraminic acid 470: 444: 430:White crystalline powder 376: 356: 321: 98: 75: 49: 44: 35: 1089:Onasemnogene abeparvovec 1060:clostridium histolyticum 643:-Glycolylneuraminic acid 1008:musculo-skeletal system 236:N-Acetylneuraminic+Acid 31:-Acetylneuraminic acid 18:N-acetylneuraminic acid 773:Microbiol Mol Biol Rev 600:Haemophilus influenzae 518:-Acetylneuraminic acid 528:) is the predominant 610:Haemophilus ducreyi 422: g·mol 32: 1254:Never to phase III 503:Infobox references 27: 1264: 1263: 597:transporter from 511:Chemical compound 509: 508: 290:CompTox Dashboard 140:Interactive image 65: 57: 16:(Redirected from 1294: 1189:Aceneuramic acid 1000: 993: 986: 977: 971: 970: 968: 960: 954: 953: 943: 911: 905: 904: 886: 877:(4): 1173–1185. 862: 856: 855: 845: 813: 807: 806: 796: 764: 758: 757: 747: 707: 701: 700: 690: 681:(9): 2817–2822. 666: 603:and the SatABCD 590:Escherichia coli 568:mucous membranes 566:associated with 493: 487: 484: 483: 465: 421: 406: 403: 397: 391: 384:Chemical formula 314: 313: 298: 296: 280: 260: 249: 238: 221: 204: 193: 182: 162: 142: 118: 87:Aceneuramic acid 63: 55: 40: 33: 21: 1302: 1301: 1297: 1296: 1295: 1293: 1292: 1291: 1287:Monosaccharides 1267: 1266: 1265: 1260: 1259: 1244:Clinical trials 1223: 1209:Hyaluronic acid 1177: 1159: 1142:Glucocorticoids 1136: 1093: 1070: 1034: 1023:and derivatives 1015: 1004: 974: 966: 962: 961: 957: 926:(10): 6727–35. 913: 912: 908: 864: 863: 859: 815: 814: 810: 766: 765: 761: 709: 708: 704: 668: 667: 660: 656: 635:Neuraminic acid 631: 619: 605:ABC transporter 584: 512: 505: 500: 499: 498:  ?) 489: 485: 481: 477: 454: 419: 409: 400: 394: 386: 372: 369: 364: 363: 352: 349: 348: 345: 339: 338: 335: 329: 328: 317: 299: 292: 283: 263: 250: 224: 185: 165: 145: 132: 121: 108: 94: 93: 71: 23: 22: 15: 12: 11: 5: 1300: 1298: 1290: 1289: 1284: 1279: 1269: 1268: 1262: 1261: 1258: 1257: 1256: 1255: 1252: 1241: 1235: 1229: 1228: 1225: 1224: 1222: 1221: 1216: 1211: 1206: 1201: 1196: 1191: 1185: 1183: 1179: 1178: 1176: 1175: 1169: 1167: 1161: 1160: 1158: 1157: 1152: 1146: 1144: 1138: 1137: 1135: 1134: 1129: 1124: 1119: 1114: 1109: 1103: 1101: 1095: 1094: 1092: 1091: 1086: 1080: 1078: 1076:Gene therapies 1072: 1071: 1069: 1068: 1063: 1055: 1050: 1044: 1042: 1036: 1035: 1033: 1032: 1026: 1024: 1017: 1016: 1005: 1003: 1002: 995: 988: 980: 973: 972: 955: 906: 871:Mol. Microbiol 857: 828:(2): 845–853. 808: 779:(1): 132–153. 759: 722:(1): 132–153. 702: 657: 655: 652: 651: 650: 645: 637: 630: 627: 618: 615: 583: 580: 510: 507: 506: 501: 479: 478: 474:standard state 471: 468: 467: 455: 450: 447: 446: 442: 441: 438: 432: 431: 428: 424: 423: 417: 411: 410: 407: 398: 392: 387: 382: 379: 378: 374: 373: 371: 370: 367: 359: 358: 357: 354: 353: 351: 350: 346: 343: 342: 340: 336: 333: 332: 324: 323: 322: 319: 318: 316: 315: 302: 300: 288: 285: 284: 282: 281: 273: 271: 265: 264: 262: 261: 253: 251: 243: 240: 239: 232: 226: 225: 223: 222: 214: 212: 206: 205: 195: 187: 186: 184: 183: 175: 173: 167: 166: 164: 163: 155: 153: 147: 146: 144: 143: 135: 133: 126: 123: 122: 120: 119: 111: 109: 104: 101: 100: 96: 95: 92: 91: 88: 85: 82: 78: 77: 73: 72: 53: 47: 46: 42: 41: 24: 14: 13: 10: 9: 6: 4: 3: 2: 1299: 1288: 1285: 1283: 1280: 1278: 1275: 1274: 1272: 1253: 1251: 1248: 1247: 1245: 1242: 1239: 1236: 1234: 1231: 1230: 1226: 1220: 1217: 1215: 1212: 1210: 1207: 1205: 1202: 1200: 1197: 1195: 1192: 1190: 1187: 1186: 1184: 1180: 1174: 1171: 1170: 1168: 1166: 1162: 1156: 1153: 1151: 1148: 1147: 1145: 1143: 1139: 1133: 1130: 1128: 1125: 1123: 1120: 1118: 1115: 1113: 1110: 1108: 1105: 1104: 1102: 1100: 1096: 1090: 1087: 1085: 1082: 1081: 1079: 1077: 1073: 1067: 1064: 1062: 1061: 1056: 1054: 1051: 1049: 1046: 1045: 1043: 1041: 1037: 1031: 1028: 1027: 1025: 1022: 1018: 1013: 1009: 1001: 996: 994: 989: 987: 982: 981: 978: 969:. Nobelpharm. 965: 959: 956: 951: 947: 942: 937: 933: 929: 925: 921: 917: 910: 907: 902: 898: 894: 890: 885: 880: 876: 872: 868: 861: 858: 853: 849: 844: 839: 835: 831: 827: 823: 819: 812: 809: 804: 800: 795: 790: 786: 782: 778: 774: 770: 763: 760: 755: 751: 746: 741: 737: 733: 729: 725: 721: 717: 713: 706: 703: 698: 694: 689: 684: 680: 676: 672: 665: 663: 659: 653: 649: 646: 644: 642: 638: 636: 633: 632: 628: 626: 624: 616: 614: 612: 611: 606: 602: 601: 596: 593:, the SiaPQM 592: 591: 581: 579: 577: 576:hemagglutinin 573: 569: 565: 560: 558: 554: 550: 549:cell membrane 546: 542: 537: 535: 531: 527: 523: 519: 517: 504: 497: 492: 475: 469: 464: 459: 456: 453: 449: 448: 445:Pharmacology 443: 439: 437: 436:Melting point 434: 433: 429: 426: 425: 418: 416: 413: 412: 388: 385: 381: 380: 375: 366: 362: 355: 341: 331: 327: 320: 312: 308: 307:DTXSID0050425 304: 303: 301: 291: 287: 286: 279: 275: 274: 272: 270: 267: 266: 259: 255: 254: 252: 246: 242: 241: 237: 233: 231: 228: 227: 220: 216: 215: 213: 211: 208: 207: 203: 199: 196: 194: 192:ECHA InfoCard 189: 188: 181: 177: 176: 174: 172: 169: 168: 161: 157: 156: 154: 152: 149: 148: 141: 137: 136: 134: 130: 125: 124: 117: 113: 112: 110: 107: 103: 102: 97: 89: 86: 83: 80: 79: 74: 69: 61: 52: 48: 43: 39: 34: 30: 19: 1277:Amino sugars 1214:Palovarotene 1204:Chondrocytes 1188: 1059: 1058:Collagenase 1030:Hydroquinine 958: 923: 920:Infect Immun 919: 909: 874: 870: 860: 825: 822:J. Bacteriol 821: 811: 776: 772: 762: 719: 715: 705: 678: 675:Microbiology 674: 640: 620: 608: 598: 588: 585: 561: 553:gangliosides 538: 525: 521: 515: 514: 513: 99:Identifiers 76:Other names 67: 59: 28: 1282:Sugar acids 1240:from market 1150:Deflazacort 1132:Viltolarsen 1112:Drisapersen 1053:Chymopapain 648:Sialic acid 617:Medical use 530:sialic acid 427:Appearance 377:Properties 198:100.004.568 160:CHEBI:61599 1271:Categories 1173:Givinostat 1155:Vamorolone 1127:Nusinersen 1122:Golodirsen 1117:Eteplirsen 1107:Casimersen 1048:Bromelains 654:References 415:Molar mass 278:GZP2782OP0 171:ChemSpider 127:3D model ( 106:CAS Number 51:IUPAC name 1250:Phase III 1238:Withdrawn 1219:Risdiplam 1199:Branaplam 736:1092-2172 572:influenza 1194:Ataluren 950:16177350 901:32085592 893:16262798 803:15007099 754:15007099 697:17768226 629:See also 466:) 452:ATC code 116:131-48-6 90:Acenobel 1066:Trypsin 1040:Enzymes 1021:Quinine 941:1230923 852:3902799 541:glycans 496:what is 494: ( 460: ( 458:M09AX05 420:309.271 245:PubChem 68:galacto 60:glycero 1233:WHO-EM 948:  938:  899:  891:  850:  843:214328 840:  801:  794:362108 791:  752:  745:362108 742:  734:  695:  545:mucins 522:Neu5Ac 491:verify 488:  361:SMILES 258:439197 219:D11016 180:392681 84:Neu5Ac 45:Names 1182:Other 967:(PDF) 897:S2CID 607:from 564:mucus 557:brain 326:InChI 151:ChEBI 129:JSmol 946:PMID 889:PMID 848:PMID 799:PMID 750:PMID 732:ISSN 693:PMID 595:TRAP 526:NANA 269:UNII 230:MeSH 210:KEGG 81:NANA 1012:M09 936:PMC 928:doi 879:doi 838:PMC 830:doi 826:164 789:PMC 781:doi 740:PMC 724:doi 683:doi 679:153 543:on 524:or 463:WHO 295:EPA 248:CID 62:-α- 1273:: 1246:: 944:. 934:. 924:73 922:. 918:. 895:. 887:. 875:58 873:. 869:. 846:. 836:. 824:. 820:. 797:. 787:. 777:68 775:. 771:. 748:. 738:. 730:. 720:68 718:. 714:. 691:. 677:. 673:. 661:^ 625:. 613:. 559:. 399:19 393:11 1014:) 1010:( 999:e 992:t 985:v 952:. 930:: 903:. 881:: 854:. 832:: 805:. 783:: 756:. 726:: 699:. 685:: 641:N 520:( 516:N 486:Y 408:9 405:O 402:N 396:H 390:C 297:) 293:( 131:) 66:- 64:D 58:- 56:D 29:N 20:)

Index

N-acetylneuraminic acid
β anomer
IUPAC name
CAS Number
131-48-6
JSmol
Interactive image
ChEBI
CHEBI:61599
ChemSpider
392681
ECHA InfoCard
100.004.568
Edit this at Wikidata
KEGG
D11016
MeSH
N-Acetylneuraminic+Acid
PubChem
439197
UNII
GZP2782OP0
CompTox Dashboard
DTXSID0050425
Edit this at Wikidata
InChI
SMILES
Chemical formula
Molar mass
Melting point

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