Knowledge

Fucose

Source πŸ“

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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".
866:"The O-linked fucose glycosylation pathway: identification and characterization of a uridine diphosphoglucose: fucose-1,3-glucosyltransferase activity from Chinese hamster ovary cells" 983:
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
1095: 299: 645: 71: 26: 1162: 665:-Fucose has several potential applications in cosmetics, pharmaceuticals, and dietary supplements 637: 1655: 1841: 1649: 1088: 1867: 1643: 907:"Exopolysaccharides enriched in rare sugars: bacterial sources, production, and applications" 861: 159: 1862: 1782: 364: 319: 235: 8: 676: 225: 63: 1872: 1066: 1016: 933: 906: 791: 720: 474: 279: 78: 33: 1058: 1020: 1008: 1000: 938: 887: 837: 783: 775: 21: 795: 1235: 1070: 1050: 992: 965: 928: 918: 877: 827: 765: 757: 594: 535: 436: 761: 644:. However, fucose at the non-reducing termini linked Ξ±-1,2 to galactose forms the 344: 1684: 1630: 1610: 1501: 551: 652: 1671: 1468: 1225: 1202: 1182: 636:-linked glycans, fucose is most commonly linked Ξ±-1,6 to the reducing terminal 576: 483: 1054: 146: 1856: 1777: 1694: 1582: 1473: 1004: 923: 882: 865: 779: 569: 996: 832: 815: 387:
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).
816:"Fucose: biosynthesis and biological function in mammals" 648:, the substructure of the A and B blood group antigens. 1033: 111:| Latest revision (diff) | Newer revision β†’ (diff) 1854: 343: 691:), thereby enhancing the in vivo cell killing. 234: 69: 1096: 814:Daniel J. Becker; John B. Lowe (July 2003). 17: 1110: 1103: 1089: 572:Fucose is the fundamental sub-unit of the 318: 955: 932: 922: 881: 831: 769: 363: 47: 681:antigen-dependent cellular cytotoxicity 14: 1855: 1084: 1027: 390:Key: SHZGCJCMOBCMKK-DHVFOXMCSA-N 298: 278: 70:Revision as of 21:00, 12 May 2024 by 44: 25: 904: 400:Key: SHZGCJCMOBCMKK-DHVFOXMCBB 334: 117: 102: 685:afucosylated monoclonal antibodies 118: 1884: 62:. The present address (URL) is a 1837: 1836: 854: 808: 586:core of fucoidan is a suspected 490: 145: 136: 486:(at 25 Β°C , 100 kPa). 976: 949: 898: 848: 802: 741: 621:. It is equivalent to 6-deoxy- 13: 1: 762:10.1016/j.foodres.2016.11.016 734: 958:J. Chem. Technol. Biotechnol 7: 750:Food Research International 694: 24:of this page, as edited by 10: 1889: 464:164.16 g/mol 119: 89: 50: 1832: 1670: 1627: 1609: 1581: 1523: 1516: 1484: 1456: 1349: 1284: 1246: 1213: 1190: 1181: 1150: 1119: 1055:10.1007/s40259-017-0223-8 679:cells and thereby reduce 480: 473: 468: 429: 409: 374: 218: 206: 172: 158: 153: 144: 135: 1163:Cyclohexane conformation 924:10.3389/fmicb.2015.00288 469:Supplementary data page 120:Not to be confused with 91: 52: 1656:Isomaltooligosaccharide 997:10.1126/science.1235681 1650:Galactooligosaccharide 883:10.1093/glycob/9.7.679 703:, the methyl ether of 200:-pyran-2,3,4,5-tetraol 1644:Fructooligosaccharide 862:Robert S. Haltiwanger 833:10.1093/glycob/cwg054 194:)-6-Methyltetrahydro- 174:Systematic IUPAC name 726:Verotoxin-producing 860:Daniel J. Moloney; 756:(Pt 3): 1011–1020. 132: 109:← Previous revision 721:Fucosyltransferase 642:-acetylglucosamine 550:. It is found on 513:Infobox references 475:Fucose (data page) 127: 45:21:00, 12 May 2024 1850: 1849: 1828: 1827: 1512: 1511: 991:(6166): 1235681. 706: 664: 617: 521:Chemical compound 519: 518: 260:Interactive image 166: 1880: 1840: 1839: 1631:oligosaccharides 1611:Tetrasaccharides 1521: 1520: 1236:Dihydroxyacetone 1188: 1187: 1105: 1098: 1091: 1082: 1081: 1075: 1074: 1040: 1031: 1025: 1024: 980: 974: 973: 953: 947: 946: 936: 926: 905:Roca, C (2015). 902: 896: 895: 885: 858: 852: 846: 845: 835: 812: 806: 800: 799: 773: 745: 728:Escherichia coli 704: 662: 624: 613: 536:chemical formula 503: 497: 494: 493: 437:Chemical formula 367: 347: 336: 322: 302: 282: 262: 238: 212: 195: 167:-galactopyranose 164: 149: 140: 133: 130: 126: 99: 97: 95: 86: 66:to this version. 61: 60: 58: 56: 46: 42: 41: 22:current revision 1888: 1887: 1883: 1882: 1881: 1879: 1878: 1877: 1853: 1852: 1851: 1846: 1824: 1685:Oat beta-glucan 1672:Polysaccharides 1666: 1629: 1623: 1605: 1577: 1508: 1502:Neuraminic acid 1480: 1452: 1345: 1280: 1242: 1209: 1183:Monosaccharides 1177: 1146: 1115: 1109: 1079: 1078: 1038: 1032: 1028: 981: 977: 954: 950: 911:Front Microbiol 903: 899: 853: 849: 807: 803: 746: 742: 737: 697: 622: 555:-linked glycans 549: 545: 541: 522: 515: 510: 509: 508:  ?) 499: 495: 491: 487: 453: 449: 445: 439: 425: 422: 421:O1(O)(OC(O)1O)C 417: 416: 405: 402: 401: 398: 392: 391: 388: 382: 381: 370: 350: 337: 325: 305: 285: 265: 252: 241: 228: 214: 210: 202: 201: 168: 128: 125: 116: 115: 114: 113: 112: 101: 100: 90: 87: 76: 74: 51: 48: 31: 29: 12: 11: 5: 1886: 1876: 1875: 1870: 1865: 1848: 1847: 1845: 1844: 1833: 1830: 1829: 1826: 1825: 1823: 1822: 1817: 1816: 1815: 1810: 1800: 1795: 1790: 1785: 1783:Levan beta 2β†’6 1780: 1775: 1774: 1773: 1757: 1746: 1745: 1744: 1728: 1719: 1714: 1713: 1712: 1707: 1702: 1697: 1692: 1687: 1676: 1674: 1668: 1667: 1665: 1664: 1659: 1653: 1647: 1641: 1635: 1633: 1625: 1624: 1622: 1621: 1615: 1613: 1607: 1606: 1604: 1603: 1598: 1593: 1587: 1585: 1583:Trisaccharides 1579: 1578: 1576: 1575: 1570: 1565: 1560: 1555: 1550: 1545: 1540: 1535: 1529: 1527: 1518: 1514: 1513: 1510: 1509: 1507: 1506: 1505: 1504: 1494: 1488: 1486: 1482: 1481: 1479: 1478: 1477: 1476: 1471: 1469:Mannoheptulose 1462: 1460: 1454: 1453: 1451: 1450: 1449: 1448: 1443: 1438: 1430: 1429: 1428: 1423: 1418: 1413: 1403: 1402: 1401: 1396: 1391: 1386: 1381: 1376: 1371: 1366: 1355: 1353: 1347: 1346: 1344: 1343: 1342: 1341: 1331: 1330: 1329: 1324: 1316: 1315: 1314: 1309: 1304: 1299: 1290: 1288: 1282: 1281: 1279: 1278: 1277: 1276: 1268: 1267: 1266: 1261: 1252: 1250: 1244: 1243: 1241: 1240: 1239: 1238: 1230: 1229: 1228: 1226:Glyceraldehyde 1219: 1217: 1211: 1210: 1208: 1207: 1206: 1205: 1203:Glycolaldehyde 1196: 1194: 1185: 1179: 1178: 1176: 1175: 1170: 1165: 1160: 1154: 1152: 1148: 1147: 1145: 1144: 1139: 1134: 1129: 1123: 1121: 1117: 1116: 1108: 1107: 1100: 1093: 1085: 1077: 1076: 1049:(3): 151–166. 1026: 975: 964:(6): 479–497. 948: 897: 876:(7): 679–687. 847: 826:(7): 41R–53R. 801: 739: 738: 736: 733: 732: 731: 723: 718: 713: 708: 696: 693: 677:Natural Killer 619:-configuration 577:polysaccharide 547: 543: 539: 520: 517: 516: 511: 489: 488: 484:standard state 481: 478: 477: 471: 470: 466: 465: 462: 456: 455: 451: 447: 443: 440: 435: 432: 431: 427: 426: 424: 423: 420: 412: 411: 410: 407: 406: 404: 403: 399: 396: 395: 393: 389: 386: 385: 377: 376: 375: 372: 371: 369: 368: 360: 358: 352: 351: 349: 348: 340: 338: 330: 327: 326: 324: 323: 315: 313: 307: 306: 304: 303: 295: 293: 287: 286: 284: 283: 275: 273: 267: 266: 264: 263: 255: 253: 246: 243: 242: 240: 239: 231: 229: 224: 221: 220: 216: 215: 208: 204: 203: 177: 176: 170: 169: 162: 156: 155: 151: 150: 142: 141: 72: 64:permanent link 27: 16: 15: 9: 6: 4: 3: 2: 1885: 1874: 1871: 1869: 1866: 1864: 1861: 1860: 1858: 1843: 1835: 1834: 1831: 1821: 1818: 1814: 1811: 1809: 1806: 1805: 1804: 1801: 1799: 1796: 1794: 1791: 1789: 1786: 1784: 1781: 1779: 1778:Hemicellulose 1776: 1772: 1769: 1768: 1767: 1766: 1762: 1758: 1756: 1755: 1751: 1747: 1743: 1740: 1739: 1738: 1737: 1733: 1729: 1727: 1723: 1720: 1718: 1715: 1711: 1708: 1706: 1703: 1701: 1698: 1696: 1693: 1691: 1688: 1686: 1683: 1682: 1681: 1678: 1677: 1675: 1673: 1669: 1663: 1660: 1657: 1654: 1651: 1648: 1645: 1642: 1640: 1637: 1636: 1634: 1632: 1626: 1620: 1617: 1616: 1614: 1612: 1608: 1602: 1599: 1597: 1594: 1592: 1589: 1588: 1586: 1584: 1580: 1574: 1571: 1569: 1566: 1564: 1561: 1559: 1556: 1554: 1551: 1549: 1546: 1544: 1541: 1539: 1536: 1534: 1531: 1530: 1528: 1526: 1525:Disaccharides 1522: 1519: 1515: 1503: 1500: 1499: 1498: 1495: 1493: 1490: 1489: 1487: 1483: 1475: 1474:Sedoheptulose 1472: 1470: 1467: 1466: 1465:Ketoheptoses 1464: 1463: 1461: 1459: 1455: 1447: 1444: 1442: 1439: 1437: 1434: 1433: 1432:Deoxy sugars 1431: 1427: 1424: 1422: 1419: 1417: 1414: 1412: 1409: 1408: 1407: 1404: 1400: 1397: 1395: 1392: 1390: 1387: 1385: 1382: 1380: 1377: 1375: 1372: 1370: 1367: 1365: 1362: 1361: 1360: 1357: 1356: 1354: 1352: 1348: 1340: 1337: 1336: 1335: 1332: 1328: 1325: 1323: 1320: 1319: 1318:Ketopentoses 1317: 1313: 1310: 1308: 1305: 1303: 1300: 1298: 1295: 1294: 1293:Aldopentoses 1292: 1291: 1289: 1287: 1283: 1275: 1272: 1271: 1269: 1265: 1262: 1260: 1257: 1256: 1255:Aldotetroses 1254: 1253: 1251: 1249: 1245: 1237: 1234: 1233: 1231: 1227: 1224: 1223: 1221: 1220: 1218: 1216: 1212: 1204: 1201: 1200: 1198: 1197: 1195: 1193: 1189: 1186: 1184: 1180: 1174: 1171: 1169: 1166: 1164: 1161: 1159: 1156: 1155: 1153: 1149: 1143: 1140: 1138: 1135: 1133: 1130: 1128: 1125: 1124: 1122: 1118: 1114: 1113:carbohydrates 1106: 1101: 1099: 1094: 1092: 1087: 1086: 1083: 1072: 1068: 1064: 1060: 1056: 1052: 1048: 1044: 1037: 1030: 1022: 1018: 1014: 1010: 1006: 1002: 998: 994: 990: 986: 979: 971: 967: 963: 959: 952: 944: 940: 935: 930: 925: 920: 916: 912: 908: 901: 893: 889: 884: 879: 875: 871: 867: 864:(July 1999). 863: 857: 851: 843: 839: 834: 829: 825: 821: 817: 811: 805: 797: 793: 789: 785: 781: 777: 772: 767: 763: 759: 755: 751: 744: 740: 730: 729: 724: 722: 719: 717: 714: 712: 709: 702: 699: 698: 692: 690: 686: 683:. Therefore, 682: 678: 674: 670: 666: 660: 658: 654: 649: 647: 643: 641: 635: 630: 628: 620: 616: 611: 607: 602: 600: 596: 592: 589: 585: 584:Ξ±(1β†’3) linked 581: 578: 575: 571: 570:cell surface. 568: 564: 560: 556: 554: 537: 533: 530: 526: 514: 507: 502: 485: 479: 476: 472: 467: 463: 461: 458: 457: 441: 438: 434: 433: 428: 419: 418: 415: 408: 394: 384: 383: 380: 373: 366: 362: 361: 359: 357: 354: 353: 346: 342: 341: 339: 333: 329: 328: 321: 317: 316: 314: 312: 309: 308: 301: 297: 296: 294: 292: 289: 288: 281: 277: 276: 274: 272: 269: 268: 261: 257: 256: 254: 250: 245: 244: 237: 233: 232: 230: 227: 223: 222: 217: 205: 199: 193: 189: 185: 181: 175: 171: 161: 157: 152: 148: 143: 139: 134: 123: 110: 106: 93: 84: 80: 75: 68: 67: 65: 54: 39: 35: 30: 23: 1868:Deoxy sugars 1759: 1748: 1730: 1662:Maltodextrin 1543:Isomaltulose 1435: 1334:Deoxy sugars 1270:Ketotetrose 1173:Mutarotation 1046: 1042: 1029: 988: 984: 978: 961: 957: 951: 914: 910: 900: 873: 870:Glycobiology 869: 850: 823: 820:Glycobiology 819: 804: 753: 749: 743: 727: 669:Fucosylation 667: 661: 653:Ξ±-fucosidase 650: 639: 633: 631: 603: 588:carbohydrate 552: 524: 523: 300:ChEMBL469449 219:Identifiers 207:Other names 197: 191: 187: 183: 179: 20:This is the 19: 18: 1863:Aldohexoses 1820:Xanthan gum 1808:Amylopectin 1680:Beta-glucan 1591:Maltotriose 1406:Ketohexoses 1359:Aldohexoses 1339:Deoxyribose 1274:Erythrulose 1232:Ketotriose 1222:Aldotriose 673:Fc receptor 610:deoxy sugar 532:deoxy sugar 430:Properties 1857:Categories 1596:Melezitose 1538:Isomaltose 1533:Cellobiose 1199:Aldodiose 771:10197/8191 735:References 716:Fucosidase 701:Digitalose 612:) and the 597:-mediated 460:Molar mass 365:28RYY2IV3F 311:ChemSpider 280:CHEBI:2181 247:3D model ( 226:CAS Number 213:-galactose 160:IUPAC name 1873:Pyranoses 1750:Galactose 1705:Cellulose 1695:Sizofiran 1619:Stachyose 1601:Raffinose 1568:Trehalose 1553:Lactulose 1374:Galactose 1297:Arabinose 1259:Erythrose 1111:Types of 1021:206548002 1005:0036-8075 780:0963-9969 657:lysosomes 655:found in 646:H antigen 627:galactose 559:mammalian 534:with the 236:2438-80-4 1842:Category 1771:Glycogen 1754:Galactan 1732:Fructose 1717:Chitosan 1690:Lentinan 1639:Acarbose 1573:Turanose 1517:Multiple 1458:Heptoses 1446:Rhamnose 1441:Fuculose 1426:Tagatose 1411:Fructose 1327:Xylulose 1322:Ribulose 1286:Pentoses 1248:Tetroses 1151:Geometry 1142:Pyranose 1137:Furanose 1063:28466278 1043:BioDrugs 1013:24385630 943:25914689 892:10362837 842:12651883 796:10531419 788:28865611 695:See also 606:hydroxyl 580:fucoidan 209:6-Deoxy- 163:6-Deoxy- 131:-Fucose 122:Fructose 83:contribs 73:Teaktl17 38:contribs 28:Teaktl17 1813:Amylose 1761:Glucose 1736:Fructan 1726:Dextran 1722:Dextrin 1700:Zymosan 1563:Sucrose 1558:Maltose 1548:Lactose 1497:Nonoses 1492:Octoses 1485:Above 7 1421:Sorbose 1416:Psicose 1394:Mannose 1379:Glucose 1369:Altrose 1351:Hexoses 1264:Threose 1215:Trioses 1120:General 1071:3722081 985:Science 934:4392319 917:: 288. 711:Fucitol 707:-fucose 599:allergy 591:antigen 574:seaweed 557:on the 506:what is 504: ( 454: 332:PubChem 1803:Starch 1798:Pectin 1793:Mannan 1788:Lignin 1765:Glucan 1742:Inulin 1710:Chitin 1436:Fucose 1399:Talose 1384:Gulose 1364:Allose 1312:Xylose 1307:Ribose 1302:Lyxose 1192:Dioses 1168:Epimer 1158:Anomer 1132:Ketose 1127:Aldose 1069:  1061:  1019:  1011:  1003:  941:  931:  890:  840:  794:  786:  778:  582:. The 563:insect 529:hexose 525:Fucose 501:verify 498:  414:SMILES 291:ChEMBL 154:Names 1658:(IMO) 1652:(GOS) 1646:(FOS) 1628:Other 1389:Idose 1067:S2CID 1039:(PDF) 1017:S2CID 792:S2CID 567:plant 527:is a 379:InChI 345:17106 320:16190 271:ChEBI 249:JSmol 92:β†’β€Žtop 53:β†’β€Žtop 1059:PMID 1009:PMID 1001:ISSN 939:PMID 888:PMID 838:PMID 784:PMID 776:ISSN 689:FUT8 593:for 565:and 356:UNII 105:diff 79:talk 34:talk 1051:doi 993:doi 989:343 966:doi 929:PMC 919:doi 878:doi 828:doi 766:hdl 758:doi 675:of 595:IgE 335:CID 96:fmt 57:fmt 43:at 1859:: 1763:/ 1752:/ 1734:/ 1724:/ 1065:. 1057:. 1047:31 1045:. 1041:. 1015:. 1007:. 999:. 987:. 962:74 960:. 937:. 927:. 913:. 909:. 886:. 872:. 868:. 836:. 824:13 822:. 818:. 790:. 782:. 774:. 764:. 754:99 752:. 659:. 638:Ξ²- 629:. 601:. 561:, 544:12 448:12 190:,5 186:,4 182:,3 178:(2 107:) 94:: 81:| 55:: 36:| 1104:e 1097:t 1090:v 1073:. 1053:: 1023:. 995:: 972:. 968:: 945:. 921:: 915:6 894:. 880:: 874:9 844:. 830:: 798:. 768:: 760:: 705:D 663:L 640:N 634:N 625:- 623:L 615:L 553:N 548:5 546:O 542:H 540:6 538:C 496:Y 452:5 450:O 446:H 444:6 442:C 251:) 211:L 198:H 196:2 192:S 188:R 184:R 180:S 165:L 129:L 124:. 103:( 98:) 88:( 85:) 77:( 59:) 49:( 40:) 32:(

Index

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Fructose


IUPAC name
Systematic IUPAC name
CAS Number
2438-80-4
JSmol
Interactive image
ChEBI
CHEBI:2181
ChEMBL
ChEMBL469449
ChemSpider
16190
PubChem
17106
UNII

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