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Fructose 1,6-bisphosphate

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Alfarouk, Khalid O.; Verduzco, Daniel; Rauch, Cyril; Muddathir, Abdel Khalig; Bashir, Adil H. H.; Elhassan, Gamal O.; Ibrahim, Muntaser E.; Orozco, Julian David Polo; Cardone, Rosa Angela; Reshkin, Stephan J.; Harguindey, Salvador (18 December 2014).
1267: 805: 1923: 1435:, have been linked to metal deposits with high iron content, although it is uncertain whether Fenton chemistry plays a substantial role in these diseases, or whether fructose 1,6-bis(phosphate) is capable of mitigating those effects. 1422:
Fructose 1,6-bis(phosphate) has also been implicated in the ability to bind and sequester Fe(II), a soluble form of iron whose oxidation to the insoluble Fe(III) is capable of generating reactive oxygen species via
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Bajic, Aleksandar; Zakrzewska J; Godjevac D; Andjus P; Jones DR; Spasic M; Spasojevic I (2011). "Relevance of the ability of fructose 1,6-bis(phosphate) to sequester ferrous but not ferric ions".
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chemistry. The ability of fructose 1,6-bis(phosphate) to bind Fe(II) may prevent such electron transfers, and thus act as an antioxidant within the body. Certain neurodegenerative diseases, like
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InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6-/m1/s1
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InChI=1/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6-/m1/s1
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The numbering of the carbon atoms indicates the fate of the carbons according to their position in fructose 6-phosphate.
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Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000.
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through distinct interactions of binding and allostery at the enzyme's catalytic site
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Click on genes, proteins and metabolites below to link to respective articles.
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Except where otherwise noted, data are given for materials in their
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Fructose 1,6-bisphosphate has only one biologically active
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The interactive pathway map can be edited at WikiPathways:
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and fructose is converted to fructose 1,6-bisphosphate.
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It is, in turn, broken down into two compounds: 2237: 1479: 231: 1269: 807: 69: 1465: 1375: 2086:Berg, Jeremy M.; Tymoczko, Stryer (2002). 1472: 1458: 503:Fructose 1,6-bisphosphate lies within the 284: 175: 153: 2161: 2062: 2052: 251: 280: 209: 2238: 2135: 510:and is produced by phosphorylation of 343:C(1(((O1)(COP(=O)(O)O)O)O)O)OP(=O)(O)O 166: 1453: 1352:|alt=Glycolysis and Gluconeogenesis 312:Key: RNBGYGVWRKECFJ-ARQDHWQXSA-N 133: 113: 606: 487:-form of this compound is common in 411: 322:Key: RNBGYGVWRKECFJ-ARQDHWQXSA 222: 192: 13: 1265: 1258: 1253: 1248: 1243: 1238: 1233: 1228: 1223: 1218: 1213: 1208: 1203: 1198: 1193: 1188: 1183: 1178: 1173: 1168: 1163: 1158: 1153: 1148: 1143: 1138: 1133: 1128: 1123: 1118: 1113: 1108: 1103: 1098: 1093: 1088: 1083: 1078: 1073: 1068: 1063: 1058: 1053: 1048: 1043: 1038: 1033: 1028: 1023: 1018: 1013: 1008: 1003: 998: 993: 988: 983: 978: 973: 968: 963: 958: 953: 948: 943: 938: 933: 928: 923: 918: 913: 908: 903: 898: 893: 888: 803: 14: 2267: 2217: 1417: 1384:"GlycolysisGluconeogenesis_WP534" 467:, known in older publications as 2223: 2005: 1982: 1957: 1922: 1886: 1863: 1846: 1815: 1790: 1756: 1726: 1703: 1684: 1658: 1641: 1622: 1605: 1580: 1563: 1544: 1527: 1502: 1365:Glycolysis and Gluconeogenesis 646: 639: 614: 600: 591: 582: 498: 491:. Upon entering the cell, most 430: 22: 479:on carbons 1 and 6 (i.e., is a 426:(at 25 °C , 100 kPa). 2178: 2129: 2112: 2079: 2027: 690:Fructose-bisphosphate aldolase 560:Fructose-bisphosphate aldolase 1: 2020: 2199:10.1016/j.carres.2010.12.008 1395: 7: 1438: 686: 683:Fructose 1,6-bisphosphatase 556:-fructose 1,6-bisphosphate 10: 2272: 2246:Monosaccharide derivatives 2094:(5th ed.). New York: 1737:Glyceraldehyde-3-phosphate 1718:Glyceraldehyde 3-phosphate 1679:Glyceraldehyde 3-phosphate 1653:Dihydroxyacetone phosphate 1399: 679: 576:dihydroxyacetone phosphate 569:glyceraldehyde 3-phosphate 520:dihydroxyacetone phosphate 516:glyceraldehyde 3-phosphate 17:Fructose 1,6-bisphosphate 2230:Fructose 1,6-bisphosphate 1617:Fructose 1,6-bisphosphate 1490: 1445:Fructose 2,6-bisphosphate 688: 681: 675: 673: 645: 638: 613: 599: 597: 590: 588: 581: 558: 546: 465:Fructose 1,6-bisphosphate 420: 394: 351: 331: 296: 53: 35: 30: 21: 2096:W.H. Freeman and Company 2054:10.18632/oncoscience.109 548:6-phosphofructo-1-kinase 211:fructose-1,6-diphosphate 1857:Phosphoglycerate mutase 1801:Phosphoglycerate kinase 1782:1,3-Bisphosphoglycerate 2136:Ishwar, Arjun (2015). 1346: 884: 2187:Carbohydrate Research 1633:Fructose-bisphosphate 1591:Phosphofructokinase-1 1345: 883: 390:340.116 2232:at Wikimedia Commons 1575:Fructose 6-phosphate 543:fructose 6-phosphate 512:fructose 6-phosphate 1949:Phosphoenolpyruvate 1555:Glucose-6-phosphate 1539:Glucose 6-phosphate 18: 2004: 1995: 1956: 1947: 1885: 1878:2-Phosphoglycerate 1876: 1845: 1838:3-Phosphoglycerate 1836: 1789: 1780: 1725: 1716: 1347: 885: 469:Harden-Young ester 453:Infobox references 16: 2228:Media related to 2154:10.1021/bi501426w 2017: 2016: 2002: 1993: 1954: 1945: 1883: 1874: 1843: 1834: 1787: 1778: 1723: 1714: 1484:metabolic pathway 1413: 779:Pathway Database. 768:Pathway Database. 757:Pathway Database. 746:Pathway Database. 735:Pathway Database. 724:Pathway Database. 713:Pathway Database. 701: 700: 508:metabolic pathway 486: 481:fructosephosphate 461:Chemical compound 459: 458: 265:CompTox Dashboard 95:Interactive image 47: 2263: 2251:Organophosphates 2227: 2211: 2210: 2182: 2176: 2175: 2165: 2148:(7): 1516–1524. 2133: 2127: 2116: 2110: 2109: 2093: 2083: 2077: 2076: 2066: 2056: 2031: 2009: 1986: 1961: 1926: 1890: 1867: 1850: 1819: 1794: 1760: 1730: 1707: 1688: 1662: 1645: 1626: 1609: 1584: 1567: 1548: 1531: 1506: 1474: 1467: 1460: 1451: 1450: 1411: 1388: 1387: 1379: 1261: 1256: 1251: 1246: 1241: 1236: 1231: 1226: 1221: 1216: 1211: 1206: 1201: 1196: 1191: 1186: 1181: 1176: 1171: 1166: 1161: 1156: 1151: 1146: 1141: 1136: 1131: 1126: 1121: 1116: 1111: 1106: 1101: 1096: 1091: 1086: 1081: 1076: 1071: 1066: 1061: 1056: 1051: 1046: 1041: 1036: 1031: 1026: 1021: 1016: 1011: 1006: 1001: 996: 991: 986: 981: 976: 971: 966: 961: 956: 951: 946: 941: 936: 931: 926: 921: 916: 911: 906: 901: 896: 891: 780: 769: 758: 747: 736: 725: 714: 650: 643: 618: 611: 604: 595: 586: 566: 555: 540: 534: 533: 484: 443: 437: 434: 433: 415: 359:Chemical formula 289: 288: 273: 271: 255: 235: 224: 213: 196: 179: 168: 157: 137: 117: 97: 73: 45: 26: 19: 15: 2271: 2270: 2266: 2265: 2264: 2262: 2261: 2260: 2236: 2235: 2220: 2215: 2214: 2183: 2179: 2134: 2130: 2117: 2113: 2106: 2084: 2080: 2047:(12): 777–802. 2032: 2028: 2023: 2018: 2013: 2012: 2011: 2010: 2000: 1989: 1988: 1987: 1979: 1978: 1975: 1971: 1968:Pyruvate kinase 1963: 1962: 1952: 1941: 1940: 1939: 1937: 1932: 1928: 1927: 1919: 1918: 1916: 1911: 1907: 1898: 1897:Phosphopyruvate 1892: 1891: 1881: 1870: 1869: 1868: 1860: 1852: 1851: 1841: 1830: 1829: 1828: 1825: 1821: 1820: 1812: 1811: 1808: 1804: 1796: 1795: 1785: 1774: 1773: 1772: 1769: 1768: 1762: 1761: 1753: 1752: 1749: 1748: 1742: 1738: 1732: 1731: 1721: 1710: 1709: 1708: 1700: 1696: 1695:Triosephosphate 1690: 1689: 1682: 1674: 1673: 1670: 1664: 1663: 1656: 1648: 1647: 1646: 1638: 1634: 1628: 1627: 1620: 1612: 1611: 1610: 1602: 1601: 1598: 1594: 1586: 1585: 1578: 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346: 345: 342: 334: 333: 332: 329: 328: 326: 325: 321: 318: 317: 315: 311: 308: 307: 299: 298: 297: 294: 293: 291: 290: 277: 275: 263: 260: 259: 257: 256: 248: 246: 240: 239: 237: 236: 228: 226: 218: 215: 214: 207: 201: 200: 198: 197: 189: 187: 181: 180: 170: 162: 161: 159: 158: 150: 148: 142: 141: 139: 138: 130: 128: 122: 121: 119: 118: 110: 108: 102: 101: 99: 98: 90: 88: 81: 78: 77: 75: 74: 66: 64: 59: 56: 55: 51: 50: 39: 33: 32: 28: 27: 9: 6: 4: 3: 2: 2268: 2257: 2254: 2252: 2249: 2247: 2244: 2243: 2241: 2231: 2226: 2222: 2221: 2208: 2204: 2200: 2196: 2192: 2188: 2181: 2173: 2169: 2164: 2159: 2155: 2151: 2147: 2143: 2139: 2132: 2125: 2124:1-57259-153-6 2121: 2115: 2107: 2105:0-7167-3051-0 2101: 2097: 2092: 2091: 2082: 2074: 2070: 2065: 2060: 2055: 2050: 2046: 2042: 2038: 2030: 2026: 2008: 1999: 1998: 1985: 1970: 1969: 1960: 1951: 1950: 1925: 1906: 1904: 1900: 1889: 1880: 1879: 1866: 1859: 1858: 1849: 1840: 1839: 1818: 1803: 1802: 1793: 1784: 1783: 1759: 1741: 1740: 1739:dehydrogenase 1729: 1720: 1719: 1706: 1699: 1698: 1687: 1681: 1680: 1669: 1661: 1655: 1654: 1644: 1637: 1636: 1625: 1619: 1618: 1608: 1593: 1592: 1583: 1577: 1576: 1566: 1559: 1558: 1547: 1541: 1540: 1530: 1515: 1514: 1505: 1499: 1498: 1489: 1485: 1482: 1475: 1470: 1468: 1463: 1461: 1456: 1455: 1452: 1446: 1443: 1442: 1436: 1434: 1430: 1426: 1415: 1409: 1403: 1385: 1378: 1374: 1368: 1363: 1355: 1268: 806: 791: 790: 786: 785: 781: 778: 774: 767: 763: 756: 752: 745: 741: 734: 730: 723: 719: 712: 708: 697: 695: 693: 691: 684: 678: 672: 669: 667: 660: 654: 653: 649: 642: 637: 634: 632: 630: 627: 625: 622: 621: 617: 610: 603: 594: 585: 580: 577: 574: 572: 570: 563: 561: 551: 549: 544: 536: 535: 531: 529: 526:activator of 525: 521: 517: 513: 509: 506: 499:In glycolysis 496: 494: 490: 482: 478: 474: 470: 466: 454: 447: 442: 425: 419: 414: 409: 406: 403: 399: 398: 395:Pharmacology 393: 389: 387: 384: 383: 363: 360: 356: 355: 350: 341: 340: 337: 330: 316: 306: 305: 302: 295: 287: 283: 282:DTXSID0048347 279: 278: 276: 266: 262: 261: 254: 250: 249: 247: 245: 242: 241: 234: 230: 229: 227: 221: 217: 216: 212: 208: 206: 203: 202: 195: 191: 190: 188: 186: 183: 182: 178: 174: 171: 169: 167:ECHA InfoCard 164: 163: 156: 152: 151: 149: 147: 144: 143: 136: 135:ChEMBL1089962 132: 131: 129: 127: 124: 123: 116: 112: 111: 109: 107: 104: 103: 96: 92: 91: 89: 85: 80: 79: 72: 68: 67: 65: 62: 58: 57: 52: 44:-phosphono-β- 43: 38: 34: 29: 25: 20: 2190: 2186: 2180: 2145: 2142:Biochemistry 2141: 2131: 2114: 2090:Biochemistry 2089: 2081: 2044: 2040: 2029: 1992: 1966: 1944: 1895: 1873: 1855: 1833: 1799: 1777: 1735: 1713: 1693: 1677: 1667: 1651: 1631: 1616: 1615: 1589: 1573: 1553: 1537: 1511: 1495: 1421: 1405: 1377: 788: 787: 783: 782: 703: 608: 502: 468: 464: 463: 54:Identifiers 41: 2041:Oncoscience 1433:Parkinson's 1429:Alzheimer's 522:. It is an 352:Properties 173:100.006.985 115:CHEBI:32966 2256:Glycolysis 2240:Categories 2021:References 1513:Hexokinase 1481:Glycolysis 524:allosteric 505:glycolysis 386:Molar mass 253:M7522JYX1H 146:ChemSpider 82:3D model ( 61:CAS Number 37:IUPAC name 1899:hydratase 1697:isomerase 1557:isomerase 1396:Isomerism 771:Compound 760:Compound 738:Compound 705:Compound 483:). The β- 2207:21232735 2172:25629396 2073:25621294 1997:Pyruvate 1771:NADH + H 1751:NADH + H 1635:aldolase 1439:See also 1410:, the β- 1402:Fructose 751:4.1.2.13 729:3.1.3.11 718:2.7.1.11 473:fructose 416:) 402:ATC code 71:488-69-7 2163:5286843 2064:4303887 1903:enolase 1497:Glucose 798:[[File: 749:Enzyme 727:Enzyme 716:Enzyme 493:glucose 446:what is 444: ( 410: ( 408:C01EB07 380: 220:PubChem 40:1,6-Di- 2205:  2170:  2160:  2122:  2102:  2071:  2061:  1931:  1910:  1765:NAD+ P 1745:NAD+ P 1425:Fenton 1408:isomer 773:C00118 762:C00111 740:C05378 707:C05345 475:sugar 441:verify 438:  336:SMILES 194:C00354 126:ChEMBL 31:Names 489:cells 471:, is 301:InChI 233:10267 106:ChEBI 84:JSmol 2203:PMID 2168:PMID 2120:ISBN 2100:ISBN 2069:PMID 1994:2 × 1946:2 × 1875:2 × 1835:2 × 1779:2 × 1715:2 × 1431:and 1367:edit 1354:edit 777:KEGG 766:KEGG 755:KEGG 744:KEGG 733:KEGG 722:KEGG 711:KEGG 518:and 244:UNII 205:MeSH 185:KEGG 155:9848 2195:doi 2191:346 2158:PMC 2150:doi 2059:PMC 2049:doi 1977:ATP 1974:ADP 1827:ATP 1824:ADP 1810:ATP 1807:ADP 1600:ADP 1597:ATP 1522:ADP 1519:ATP 775:at 764:at 753:at 742:at 731:at 720:at 709:at 629:ADP 624:ATP 413:WHO 270:EPA 223:CID 2242:: 2201:. 2189:. 2166:. 2156:. 2146:54 2144:. 2140:. 2098:. 2067:. 2057:. 2043:. 2039:. 1356:]] 665:O 552:β- 537:β- 374:12 370:14 2209:. 2197:: 2174:. 2152:: 2126:. 2108:. 2075:. 2051:: 2045:1 1938:O 1936:2 1934:H 1917:O 1915:2 1913:H 1905:) 1901:( 1767:i 1747:i 1672:+ 1668:+ 1473:e 1466:t 1459:v 1412:D 1386:. 1260:] 1255:] 1250:] 1245:] 1240:] 1235:] 1230:] 1225:] 1220:] 1215:] 1210:] 1205:] 1200:] 1195:] 1190:] 1185:] 1180:] 1175:] 1170:] 1165:] 1160:] 1155:] 1150:] 1145:] 1140:] 1135:] 1130:] 1125:] 1120:] 1115:] 1110:] 1105:] 1100:] 1095:] 1090:] 1085:] 1080:] 1075:] 1070:] 1065:] 1060:] 1055:] 1050:] 1045:] 1040:] 1035:] 1030:] 1025:] 1020:] 1015:] 1010:] 1005:] 1000:] 995:] 990:] 985:] 980:] 975:] 970:] 965:] 960:] 955:] 950:] 945:] 940:] 935:] 930:] 925:] 920:] 915:] 910:] 905:] 900:] 895:] 890:] 663:2 661:H 657:i 655:P 609:+ 567:- 565:D 554:D 541:- 539:D 485:D 436:Y 378:2 376:P 372:O 368:H 366:6 364:C 272:) 268:( 86:) 46:D 42:O

Index


IUPAC name
CAS Number
488-69-7
JSmol
Interactive image
ChEBI
CHEBI:32966
ChEMBL
ChEMBL1089962
ChemSpider
9848
ECHA InfoCard
100.006.985
Edit this at Wikidata
KEGG
C00354
MeSH
fructose-1,6-diphosphate
PubChem
10267
UNII
M7522JYX1H
CompTox Dashboard
DTXSID0048347
Edit this at Wikidata
InChI
SMILES
Chemical formula
Molar mass

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