Knowledge

Fucose

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Garcia-Vaquero, M.; Rajauria, G.; O'Doherty, J.V.; Sweeney, T. (2017-09-01). "Polysaccharides from macroalgae: Recent advances, innovative technologies and challenges in extraction and purification".
762:"The O-linked fucose glycosylation pathway: identification and characterization of a uridine diphosphoglucose: fucose-1,3-glucosyltransferase activity from Chinese hamster ovary cells" 879:
Dalziel, Martin; Crispin, Max; Scanlan, Christopher N.; Zitzmann, Nicole; Dwek, Raymond A. (2014-01-03). "Emerging Principles for the Therapeutic Exploitation of Glycosylation".
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In the fucose-containing glycan structures, fucosylated glycans, fucose can exist as a terminal modification or serve as an attachment point for adding other sugars. In human
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have been designed to recruit the immune system to cancers cells have been manufactured in cell lines deficient in the enzyme for core fucosylation (
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Vanhooren, PT (1999). "L-fucose: occurrence, physiological role, chemical, enzymatic and microbial synthesis".
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Two structural features distinguish fucose from other six-carbon sugars present in mammals: the lack of a
991: 195: 541: 1058: 561:-Fucose has several potential applications in cosmetics, pharmaceuticals, and dietary supplements 533: 1551: 1737: 1545: 984: 1763: 1539: 803:"Exopolysaccharides enriched in rare sugars: bacterial sources, production, and applications" 757: 55: 1758: 1678: 260: 215: 131: 8: 572: 121: 1768: 962: 912: 829: 802: 687: 616: 370: 175: 954: 916: 904: 896: 834: 783: 733: 679: 671: 691: 1131: 966: 946: 888: 861: 824: 814: 773: 723: 661: 653: 490: 431: 332: 657: 540:. However, fucose at the non-reducing termini linked α-1,2 to galactose forms the 240: 1580: 1526: 1506: 1397: 447: 548: 1567: 1364: 1121: 1098: 1078: 532:-linked glycans, fucose is most commonly linked α-1,6 to the reducing terminal 472: 379: 950: 42: 1752: 1673: 1590: 1478: 1369: 900: 819: 778: 761: 675: 465: 892: 728: 711: 283:
InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6?/m0/s1
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InChI=1/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6?/m0/s1
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10.1002/(SICI)1097-4660(199906)74:6<479::AID-JCTB76>3.0.CO;2-E
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Fucose is released from fucose-containing polymers by an enzyme called
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Except where otherwise noted, data are given for materials in their
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group on the carbon at the 6-position (C-6) (thereby making it a
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of antibodies has been established to reduce binding to the
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Yu, X; Marshall, MJE; Cragg, MS; Crispin, M (June 2017).
712:"Fucose: biosynthesis and biological function in mammals" 544:, the substructure of the A and B blood group antigens. 929: 1750: 239: 587:), thereby enhancing the in vivo cell killing. 130: 992: 710:Daniel J. Becker; John B. Lowe (July 2003). 1006: 999: 985: 468:Fucose is the fundamental sub-unit of the 214: 851: 828: 818: 777: 727: 665: 259: 577:antigen-dependent cellular cytotoxicity 1751: 980: 923: 286:Key: SHZGCJCMOBCMKK-DHVFOXMCSA-N 194: 174: 800: 296:Key: SHZGCJCMOBCMKK-DHVFOXMCBB 230: 13: 581:afucosylated monoclonal antibodies 14: 1780: 1733: 1732: 750: 704: 482:core of fucoidan is a suspected 386: 41: 32: 382:(at 25 °C , 100 kPa). 872: 845: 794: 744: 698: 637: 517:. It is equivalent to 6-deoxy- 1: 658:10.1016/j.foodres.2016.11.016 630: 854:J. Chem. Technol. Biotechnol 7: 646:Food Research International 590: 10: 1785: 360:164.16 g/mol 15: 1728: 1566: 1523: 1505: 1477: 1419: 1412: 1380: 1352: 1245: 1180: 1142: 1109: 1086: 1077: 1046: 1015: 951:10.1007/s40259-017-0223-8 575:cells and thereby reduce 376: 369: 364: 325: 305: 270: 114: 102: 68: 54: 49: 40: 31: 1059:Cyclohexane conformation 820:10.3389/fmicb.2015.00288 365:Supplementary data page 16:Not to be confused with 1552:Isomaltooligosaccharide 893:10.1126/science.1235681 1546:Galactooligosaccharide 779:10.1093/glycob/9.7.679 599:, the methyl ether of 96:-pyran-2,3,4,5-tetraol 1540:Fructooligosaccharide 758:Robert S. Haltiwanger 729:10.1093/glycob/cwg054 90:)-6-Methyltetrahydro- 70:Systematic IUPAC name 622:Verotoxin-producing 756:Daniel J. Moloney; 652:(Pt 3): 1011–1020. 28: 617:Fucosyltransferase 538:-acetylglucosamine 446:. It is found on 409:Infobox references 371:Fucose (data page) 23: 1746: 1745: 1724: 1723: 1408: 1407: 887:(6166): 1235681. 602: 560: 513: 417:Chemical compound 415: 414: 156:Interactive image 62: 1776: 1736: 1735: 1527:oligosaccharides 1507:Tetrasaccharides 1417: 1416: 1132:Dihydroxyacetone 1084: 1083: 1001: 994: 987: 978: 977: 971: 970: 936: 927: 921: 920: 876: 870: 869: 849: 843: 842: 832: 822: 801:Roca, C (2015). 798: 792: 791: 781: 754: 748: 742: 741: 731: 708: 702: 696: 695: 669: 641: 624:Escherichia coli 600: 558: 520: 509: 432:chemical formula 399: 393: 390: 389: 333:Chemical formula 263: 243: 232: 218: 198: 178: 158: 134: 108: 91: 63:-galactopyranose 60: 45: 36: 29: 26: 22: 1784: 1783: 1779: 1778: 1777: 1775: 1774: 1773: 1749: 1748: 1747: 1742: 1720: 1581:Oat beta-glucan 1568:Polysaccharides 1562: 1525: 1519: 1501: 1473: 1404: 1398:Neuraminic acid 1376: 1348: 1241: 1176: 1138: 1105: 1079:Monosaccharides 1073: 1042: 1011: 1005: 975: 974: 934: 928: 924: 877: 873: 850: 846: 807:Front Microbiol 799: 795: 749: 745: 703: 699: 642: 638: 633: 593: 518: 451:-linked glycans 445: 441: 437: 418: 411: 406: 405: 404:  ?) 395: 391: 387: 383: 349: 345: 341: 335: 321: 318: 317:O1(O)(OC(O)1O)C 313: 312: 301: 298: 297: 294: 288: 287: 284: 278: 277: 266: 246: 233: 221: 201: 181: 161: 148: 137: 124: 110: 106: 98: 97: 64: 24: 21: 12: 11: 5: 1782: 1772: 1771: 1766: 1761: 1744: 1743: 1741: 1740: 1729: 1726: 1725: 1722: 1721: 1719: 1718: 1713: 1712: 1711: 1706: 1696: 1691: 1686: 1681: 1679:Levan beta 2→6 1676: 1671: 1670: 1669: 1653: 1642: 1641: 1640: 1624: 1615: 1610: 1609: 1608: 1603: 1598: 1593: 1588: 1583: 1572: 1570: 1564: 1563: 1561: 1560: 1555: 1549: 1543: 1537: 1531: 1529: 1521: 1520: 1518: 1517: 1511: 1509: 1503: 1502: 1500: 1499: 1494: 1489: 1483: 1481: 1479:Trisaccharides 1475: 1474: 1472: 1471: 1466: 1461: 1456: 1451: 1446: 1441: 1436: 1431: 1425: 1423: 1414: 1410: 1409: 1406: 1405: 1403: 1402: 1401: 1400: 1390: 1384: 1382: 1378: 1377: 1375: 1374: 1373: 1372: 1367: 1365:Mannoheptulose 1358: 1356: 1350: 1349: 1347: 1346: 1345: 1344: 1339: 1334: 1326: 1325: 1324: 1319: 1314: 1309: 1299: 1298: 1297: 1292: 1287: 1282: 1277: 1272: 1267: 1262: 1251: 1249: 1243: 1242: 1240: 1239: 1238: 1237: 1227: 1226: 1225: 1220: 1212: 1211: 1210: 1205: 1200: 1195: 1186: 1184: 1178: 1177: 1175: 1174: 1173: 1172: 1164: 1163: 1162: 1157: 1148: 1146: 1140: 1139: 1137: 1136: 1135: 1134: 1126: 1125: 1124: 1122:Glyceraldehyde 1115: 1113: 1107: 1106: 1104: 1103: 1102: 1101: 1099:Glycolaldehyde 1092: 1090: 1081: 1075: 1074: 1072: 1071: 1066: 1061: 1056: 1050: 1048: 1044: 1043: 1041: 1040: 1035: 1030: 1025: 1019: 1017: 1013: 1012: 1004: 1003: 996: 989: 981: 973: 972: 945:(3): 151–166. 922: 871: 860:(6): 479–497. 844: 793: 772:(7): 679–687. 743: 722:(7): 41R–53R. 697: 635: 634: 632: 629: 628: 627: 619: 614: 609: 604: 592: 589: 573:Natural Killer 515:-configuration 473:polysaccharide 443: 439: 435: 416: 413: 412: 407: 385: 384: 380:standard state 377: 374: 373: 367: 366: 362: 361: 358: 352: 351: 347: 343: 339: 336: 331: 328: 327: 323: 322: 320: 319: 316: 308: 307: 306: 303: 302: 300: 299: 295: 292: 291: 289: 285: 282: 281: 273: 272: 271: 268: 267: 265: 264: 256: 254: 248: 247: 245: 244: 236: 234: 226: 223: 222: 220: 219: 211: 209: 203: 202: 200: 199: 191: 189: 183: 182: 180: 179: 171: 169: 163: 162: 160: 159: 151: 149: 142: 139: 138: 136: 135: 127: 125: 120: 117: 116: 112: 111: 104: 100: 99: 73: 72: 66: 65: 58: 52: 51: 47: 46: 38: 37: 9: 6: 4: 3: 2: 1781: 1770: 1767: 1765: 1762: 1760: 1757: 1756: 1754: 1739: 1731: 1730: 1727: 1717: 1714: 1710: 1707: 1705: 1702: 1701: 1700: 1697: 1695: 1692: 1690: 1687: 1685: 1682: 1680: 1677: 1675: 1674:Hemicellulose 1672: 1668: 1665: 1664: 1663: 1662: 1658: 1654: 1652: 1651: 1647: 1643: 1639: 1636: 1635: 1634: 1633: 1629: 1625: 1623: 1619: 1616: 1614: 1611: 1607: 1604: 1602: 1599: 1597: 1594: 1592: 1589: 1587: 1584: 1582: 1579: 1578: 1577: 1574: 1573: 1571: 1569: 1565: 1559: 1556: 1553: 1550: 1547: 1544: 1541: 1538: 1536: 1533: 1532: 1530: 1528: 1522: 1516: 1513: 1512: 1510: 1508: 1504: 1498: 1495: 1493: 1490: 1488: 1485: 1484: 1482: 1480: 1476: 1470: 1467: 1465: 1462: 1460: 1457: 1455: 1452: 1450: 1447: 1445: 1442: 1440: 1437: 1435: 1432: 1430: 1427: 1426: 1424: 1422: 1421:Disaccharides 1418: 1415: 1411: 1399: 1396: 1395: 1394: 1391: 1389: 1386: 1385: 1383: 1379: 1371: 1370:Sedoheptulose 1368: 1366: 1363: 1362: 1361:Ketoheptoses 1360: 1359: 1357: 1355: 1351: 1343: 1340: 1338: 1335: 1333: 1330: 1329: 1328:Deoxy sugars 1327: 1323: 1320: 1318: 1315: 1313: 1310: 1308: 1305: 1304: 1303: 1300: 1296: 1293: 1291: 1288: 1286: 1283: 1281: 1278: 1276: 1273: 1271: 1268: 1266: 1263: 1261: 1258: 1257: 1256: 1253: 1252: 1250: 1248: 1244: 1236: 1233: 1232: 1231: 1228: 1224: 1221: 1219: 1216: 1215: 1214:Ketopentoses 1213: 1209: 1206: 1204: 1201: 1199: 1196: 1194: 1191: 1190: 1189:Aldopentoses 1188: 1187: 1185: 1183: 1179: 1171: 1168: 1167: 1165: 1161: 1158: 1156: 1153: 1152: 1151:Aldotetroses 1150: 1149: 1147: 1145: 1141: 1133: 1130: 1129: 1127: 1123: 1120: 1119: 1117: 1116: 1114: 1112: 1108: 1100: 1097: 1096: 1094: 1093: 1091: 1089: 1085: 1082: 1080: 1076: 1070: 1067: 1065: 1062: 1060: 1057: 1055: 1052: 1051: 1049: 1045: 1039: 1036: 1034: 1031: 1029: 1026: 1024: 1021: 1020: 1018: 1014: 1010: 1009:carbohydrates 1002: 997: 995: 990: 988: 983: 982: 979: 968: 964: 960: 956: 952: 948: 944: 940: 933: 926: 918: 914: 910: 906: 902: 898: 894: 890: 886: 882: 875: 867: 863: 859: 855: 848: 840: 836: 831: 826: 821: 816: 812: 808: 804: 797: 789: 785: 780: 775: 771: 767: 763: 760:(July 1999). 759: 753: 747: 739: 735: 730: 725: 721: 717: 713: 707: 701: 693: 689: 685: 681: 677: 673: 668: 663: 659: 655: 651: 647: 640: 636: 626: 625: 620: 618: 615: 613: 610: 608: 605: 598: 595: 594: 588: 586: 582: 579:. Therefore, 578: 574: 570: 566: 562: 556: 554: 550: 545: 543: 539: 537: 531: 526: 524: 516: 512: 507: 503: 498: 496: 492: 488: 485: 481: 480:α(1→3) linked 477: 474: 471: 467: 466:cell surface. 464: 460: 456: 452: 450: 433: 429: 426: 422: 410: 403: 398: 381: 375: 372: 368: 363: 359: 357: 354: 353: 337: 334: 330: 329: 324: 315: 314: 311: 304: 290: 280: 279: 276: 269: 262: 258: 257: 255: 253: 250: 249: 242: 238: 237: 235: 229: 225: 224: 217: 213: 212: 210: 208: 205: 204: 197: 193: 192: 190: 188: 185: 184: 177: 173: 172: 170: 168: 165: 164: 157: 153: 152: 150: 146: 141: 140: 133: 129: 128: 126: 123: 119: 118: 113: 101: 95: 89: 85: 81: 77: 71: 67: 57: 53: 48: 44: 39: 35: 30: 19: 1764:Deoxy sugars 1655: 1644: 1626: 1558:Maltodextrin 1439:Isomaltulose 1331: 1230:Deoxy sugars 1166:Ketotetrose 1069:Mutarotation 942: 938: 925: 884: 880: 874: 857: 853: 847: 810: 806: 796: 769: 766:Glycobiology 765: 746: 719: 716:Glycobiology 715: 700: 649: 645: 639: 623: 565:Fucosylation 563: 557: 549:α-fucosidase 546: 535: 529: 527: 499: 484:carbohydrate 448: 420: 419: 196:ChEMBL469449 115:Identifiers 103:Other names 93: 87: 83: 79: 75: 1759:Aldohexoses 1716:Xanthan gum 1704:Amylopectin 1576:Beta-glucan 1487:Maltotriose 1302:Ketohexoses 1255:Aldohexoses 1235:Deoxyribose 1170:Erythrulose 1128:Ketotriose 1118:Aldotriose 569:Fc receptor 506:deoxy sugar 428:deoxy sugar 326:Properties 1753:Categories 1492:Melezitose 1434:Isomaltose 1429:Cellobiose 1095:Aldodiose 667:10197/8191 631:References 612:Fucosidase 597:Digitalose 508:) and the 493:-mediated 356:Molar mass 261:28RYY2IV3F 207:ChemSpider 176:CHEBI:2181 143:3D model ( 122:CAS Number 109:-galactose 56:IUPAC name 1769:Pyranoses 1646:Galactose 1601:Cellulose 1591:Sizofiran 1515:Stachyose 1497:Raffinose 1464:Trehalose 1449:Lactulose 1270:Galactose 1193:Arabinose 1155:Erythrose 1007:Types of 917:206548002 901:0036-8075 676:0963-9969 553:lysosomes 551:found in 542:H antigen 523:galactose 455:mammalian 430:with the 132:2438-80-4 1738:Category 1667:Glycogen 1650:Galactan 1628:Fructose 1613:Chitosan 1586:Lentinan 1535:Acarbose 1469:Turanose 1413:Multiple 1354:Heptoses 1342:Rhamnose 1337:Fuculose 1322:Tagatose 1307:Fructose 1223:Xylulose 1218:Ribulose 1182:Pentoses 1144:Tetroses 1047:Geometry 1038:Pyranose 1033:Furanose 959:28466278 939:BioDrugs 909:24385630 839:25914689 788:10362837 738:12651883 692:10531419 684:28865611 591:See also 502:hydroxyl 476:fucoidan 105:6-Deoxy- 59:6-Deoxy- 27:-Fucose 18:Fructose 1709:Amylose 1657:Glucose 1632:Fructan 1622:Dextran 1618:Dextrin 1596:Zymosan 1459:Sucrose 1454:Maltose 1444:Lactose 1393:Nonoses 1388:Octoses 1381:Above 7 1317:Sorbose 1312:Psicose 1290:Mannose 1275:Glucose 1265:Altrose 1247:Hexoses 1160:Threose 1111:Trioses 1016:General 967:3722081 881:Science 830:4392319 813:: 288. 607:Fucitol 603:-fucose 495:allergy 487:antigen 470:seaweed 453:on the 402:what is 400: ( 350: 228:PubChem 1699:Starch 1694:Pectin 1689:Mannan 1684:Lignin 1661:Glucan 1638:Inulin 1606:Chitin 1332:Fucose 1295:Talose 1280:Gulose 1260:Allose 1208:Xylose 1203:Ribose 1198:Lyxose 1088:Dioses 1064:Epimer 1054:Anomer 1028:Ketose 1023:Aldose 965:  957:  915:  907:  899:  837:  827:  786:  736:  690:  682:  674:  478:. The 459:insect 425:hexose 421:Fucose 397:verify 394:  310:SMILES 187:ChEMBL 50:Names 1554:(IMO) 1548:(GOS) 1542:(FOS) 1524:Other 1285:Idose 963:S2CID 935:(PDF) 913:S2CID 688:S2CID 463:plant 423:is a 275:InChI 241:17106 216:16190 167:ChEBI 145:JSmol 955:PMID 905:PMID 897:ISSN 835:PMID 784:PMID 734:PMID 680:PMID 672:ISSN 585:FUT8 489:for 461:and 252:UNII 947:doi 889:doi 885:343 862:doi 825:PMC 815:doi 774:doi 724:doi 662:hdl 654:doi 571:of 491:IgE 231:CID 1755:: 1659:/ 1648:/ 1630:/ 1620:/ 961:. 953:. 943:31 941:. 937:. 911:. 903:. 895:. 883:. 858:74 856:. 833:. 823:. 809:. 805:. 782:. 768:. 764:. 732:. 720:13 718:. 714:. 686:. 678:. 670:. 660:. 650:99 648:. 555:. 534:β- 525:. 497:. 457:, 440:12 344:12 86:,5 82:,4 78:,3 74:(2 1000:e 993:t 986:v 969:. 949:: 919:. 891:: 868:. 864:: 841:. 817:: 811:6 790:. 776:: 770:9 740:. 726:: 694:. 664:: 656:: 601:D 559:L 536:N 530:N 521:- 519:L 511:L 449:N 444:5 442:O 438:H 436:6 434:C 392:Y 348:5 346:O 342:H 340:6 338:C 147:) 107:L 94:H 92:2 88:S 84:R 80:R 76:S 61:L 25:L 20:.

Index

Fructose


IUPAC name
Systematic IUPAC name
CAS Number
2438-80-4
JSmol
Interactive image
ChEBI
CHEBI:2181
ChEMBL
ChEMBL469449
ChemSpider
16190
PubChem
17106
UNII
28RYY2IV3F
InChI
SMILES
Chemical formula
Molar mass
Fucose (data page)
standard state
verify
what is
Infobox references
hexose
deoxy sugar

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