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Hexose

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Although all hexoses have similar structures and share some general properties, each enantiomer pair has its own chemistry. Fructose is soluble in water, alcohol, and ether. The two enantiomers of each pair generally have vastly different biological properties.
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The linear form does not crystallize, and exists only in small amounts in water solutions, where it is in equilibrium with the closed forms. Nevertheless, it plays an essential role as the intermediate stage between those closed forms.
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It has been known since 1926 that hexoses in the crystalline solid state assume the cyclic form. The "α" and "β" forms, which are not enantiomers, will usually crystallize separately as distinct species. For example,
1194:, which may have either of two configurations, depending on the position of the new hydroxyl. Therefore, each hexose in linear form can produce two distinct closed forms, identified by prefixes "α" and "β". 125:
Hexoses exist in two forms, open-chain or cyclic, that easily convert into each other in aqueous solutions. The open-chain form of a hexose, which usually is favored in solutions, has the general structure
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Like most monosaccharides with five or more carbons, each aldohexose or 2-ketohexose also exists in one or more cyclic (closed-chain) forms, derived from the open-chain form by an
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In particular, the "α" and "β" forms can convert to into each other by returning to the open-chain form and then closing in the opposite configuration. This process is called
651:, from left to right, indicate the position of the hydroxyls on carbons 4, 3, and 2, respectively: to the right if the bit value is 0, and to the left if the value is 1. 766:
Besides the 2-ketoses, there are only the 3-Ketoses, and they do not exist in nature, although at least one 3-ketohexose has been synthesized, with great difficulty.
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In the linear form, the 2-ketohexoses have three chiral centers and therefore eight possible stereoisomers (2), comprising four pairs of enantiomers. The four
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device for remembering the order given above, which corresponds to the configurations about the chiral centers when ordered as 3-bit binary strings:
253:. However, the 3-ketohexoses have not been observed in nature, and are difficult to synthesize; so the term "ketohexose" usually means 2-ketohexose. 2022: 1183:
with five- or six-membered ring, respectively. If the sugar is a 2-ketohexose, it can only involve the hydroxyl in carbon 5, and will create a
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If the sugar is an aldohexose, with the carbonyl in position 1, the reaction may involve the hydroxyl on carbon 4 or carbon 5, creating a
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Akira Sera (1962): "Studies on the Chemical Decomposition of Simple Sugars. XIII. Separation of the So-called Glutose (a 3-Ketohexose)".
1105:, and was claimed to be a 3-ketohexose. However, subsequent studies showed that the substance was a mixture of various other compounds. 1307:
of +112° and melting point of 146 °C, as well as a β crystal that has specific rotation of +19° and melting point of 150 °C.
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C. A. Lobry de Bruyn and W. Alberda van Ekenstein (1897): "Action des alcalis sur les sucres. VI: La glutose et la pseudo‐fructose".
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forms have the hydroxyls on carbons 3, 4,and 5 reversed. Below are depiction of the eight isomers in an alternative style:
1744:-altrose", issued 1990-10-30, assigned to Government of the United States of America, Secretary of Agriculture 2015: 1790: 1655: 348:
The aldohexoses are a subclass of the hexoses which, in the linear form, have the carbonyl at carbon 1, forming an
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that can be described as derived from hexoses by replacement of one or more hydroxyl groups with hydrogen atoms.
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of the molecule, is to the right or to the left of the axis, respectively. These labels are independent of the
2787: 2082: 2575: 1132: 1994: 1982: 2761: 2569: 2008: 759:-containing hexose. The important ketohexoses are the 2-ketohexoses, and the most important 2-ketose is 539: 1062:
In theory, the ketohexoses include also the 3-ketohexoses, which have the carbonyl in position 3; namely
2563: 1176:. The conventional numbering of the carbons in the closed form is the same as in the open-chain form. 1120: 1735: 264:. Each pair has a conventional name (like "glucose" or "fructose"), and the two members are labeled " 2702: 1109: 655: 443: 419: 1116: 847: 563: 491: 395: 1168:, that has the same ring. If the cycle has four carbon atoms (five in total), the form is called 902: 1932:
George L. Clark, Hung Kao, Louis Sattler, and F. W. Zerban (1949): "Chemical Nature of Glutose".
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atoms. The carbons are commonly numbered 1 to 6 starting at the end closest to the carbonyl.
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indicating the carbon with the affected hydroxyl. Some examples of biological interest are
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The term "hexose" may sometimes be used to include the deoxyhexoses, which have one or more
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that differ in the spatial position of the hydroxyl groups. These species occur in pairs of
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of the isomers. In general, only one of the two enantiomers occurs naturally (for example,
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If the cycle has five carbon atoms (six atoms in total), the closed form is called a
1014: 880: 644: 368: 2581: 2462: 2444: 2092: 2032: 1407:-Tagatose is a rare natural ketohexose that is found in small quantities in food. 1315: 1191: 1078: 372: 295: 257: 219: 204: 180: 2739: 2727: 2599: 2510: 2258: 2253: 2193: 1430: 1143: 1094: 234:. Otherwise, if the carbonyl position is 2 or 3, the sugar is a derivative of a 157: 1337:
of 10.28, will only deprotonate at high pH, so are marginally less stable than
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is responsible for the sweet taste of many fruits, and is a building block of
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from 0 to 7, namely 000, 001, 010, 011, 100, 101, 110, 111. The three
480: 456: 432: 361: 208: 184: 56: 47: 747:-isomers; with all hydroxyls reversed, including the one on carbon 5. 256:
In the linear form, there are 16 aldohexoses and eight 2-ketohexoses,
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2-Ketohexoses are stable over a wide pH range, and with a primary p
2308: 2111: 1542: 1162: 528: 299: 172:). The remaining bonds of the carbon atoms are satisfied by seven 1115:, through a rather complex route, was first reported in 1961 by 2004: 598:-altrose occur in living organisms, but only three are common: 1150:) between the two carbon atoms, thus creating a ring with one 648: 1911:
Recueil des Travaux Chimiques des Pays-Bas et de la Belgique
622:-isomers are generally absent in living organisms; however, 276:-", depending on whether the hydroxyl in position 5, in the 1135:
between the carbonyl group and one of the hydroxyl groups.
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The unequivocal synthesis and isolation of a 3-ketohexose,
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Robert Thornton Morrison and Robert Neilson Boyd (1998):
1398:-Sorbose is commonly used in the commercial synthesis of 1349:
The aldohexose that is most important in biochemistry is
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When drawn in this order, the Fischer projections of the
628:-altrose has been isolated from strains of the bacterium 741:-aldohexoses are the mirror images of the corresponding 148:
is 1, 2, 3, 4, 5. Namely, five of the carbons have one
1451:). It is named as the parent hexose, with the prefix " 1738:, Stack; Robert J., "Microbial production of 1599:
Essentials of Carbohydrate Chemistry and Biochemistry
191:) and as building blocks of other compounds such as 2590: 2547: 2529: 2501: 2443: 2436: 2404: 2376: 2269: 2204: 2166: 2133: 2110: 2101: 2070: 2039: 1761: 305:The term "hexose" sometimes is assumed to include 1714:George U. Yuen and James M. Sugihara (1961): "". 1142:group into a hydroxyl, and the hydroxyl into an 643:-aldohexoses can be identified with the 3-digit 103:atoms. The chemical formula for all hexoses is 1880: 1878: 1081:product obtained by treatment of fructose with 218:When the carbonyl is in position 1, forming an 1846: 1844: 1818: 1816: 2016: 1190:The closure turns the carboxyl carbon into a 8: 1928: 1926: 211:) by a condensation reaction that makes 1,6- 1624: 1622: 1620: 1618: 2440: 2107: 2023: 2009: 2001: 1710: 1708: 1706: 1685: 1683: 1681: 1679: 1589: 1587: 1585: 1583: 1954:Bulletin of the Chemical Society of Japan 1956:, volume 35, issue 12, pages 2031-2033. 1069: 1065: 355: 328: 324: 320: 136: 129: 114: 110: 106: 1718:, volume 26, issue 5, pages 1598-1601. 1579: 966: 876: 777: 391: 367:In linear form, an aldohexose has four 183:, both as isolated molecules (such as 1934:Industrial & Engineering Chemistry 658:is said to have devised the following 1936:, volume 41, issue 3, pages 530-533. 1913:, volume 16, issue 9, pages 274-281. 1303:-glucose forms an α crystal that has 7: 1631:Essentials of Carbohydrate Chemistry 371:, which give 16 possible aldohexose 1764:The vocabulary of organic chemistry 179:Hexoses are extremely important in 735:The Fischer diagrams of the eight 25: 379:. The linear forms of the eight 360:. The most important example is 317:: compounds with general formula 2757: 2756: 1988: 1976: 1499:-glucose), found as part of the 1255: 1237: 1219: 1201: 1035: 1013: 991: 969: 945: 923: 901: 879: 846: 824: 802: 780: 562: 538: 514: 490: 466: 442: 418: 394: 55: 34: 1154:atom and four or five carbons. 1504:sulfoquinovosyl diacylglycerol 77:Two important hexoses, in the 1: 1042: 1020: 998: 976: 952: 930: 908: 886: 853: 831: 809: 787: 569: 545: 521: 497: 473: 449: 425: 401: 1716:Journal of Organic Chemistry 160:, and one has an oxo group ( 1760:Milton Orchin, ed. (1980). 1345:Natural occurrence and uses 1187:with a five-membered ring. 2804: 1428: 375:(2),comprising 8 pairs of 352:derivative with structure 226:), the sugar is called an 2752: 1601:(1 ed.). Wiley-VCH. 631:Butyrivibrio fibrisolvens 2083:Cyclohexane conformation 1919:10.1002/recl.18970160903 1891:pubchem.ncbi.nlm.nih.gov 1863:pubchem.ncbi.nlm.nih.gov 1829:pubchem.ncbi.nlm.nih.gov 1801:pubchem.ncbi.nlm.nih.gov 1664:pubchem.ncbi.nlm.nih.gov 1633:(1 ed.). Springer. 1384:occurs naturally as the 156:) each, connected by a 99:(simple sugar) with six 2576:Isomaltooligosaccharide 1374:occur naturally as the 1138:The reaction turns the 2570:Galactooligosaccharide 1629:John F. Robyt (1997). 1133:internal rearrangement 2564:Fructooligosaccharide 1736:US patent 4966845 1089:, was given the name 592:-isomers, all except 385:-aldohexoses, in the 290:-glucose) and can be 27:6-carbon simple sugar 1997:at Wikimedia Commons 1985:at Wikimedia Commons 1962:10.1246/bcsj.35.2031 1421:, the common sugar. 242:, a special case of 230:, a special case of 203:. Hexoses can form 1942:10.1021/ie50471a020 1724:10.1021/jo01064a070 1595:Thisbe K. Lindhorst 1322:Chemical properties 1172:after the compound 246:; specifically, an 1380:-isomers, whereas 1362:The 2-ketohexoses 1288:Haworth projection 1286:-fructose, in the 1087:lead(II) hydroxide 868:The corresponding 755:A ketohexose is a 387:Fischer projection 278:Fischer projection 238:, and is called a 152:functional group ( 122:is 180.156 g/mol. 79:Fischer projection 2770: 2769: 2748: 2747: 2432: 2431: 1993:Media related to 1981:Media related to 1775:978-0-471-04491-8 1691:Organic Chemistry 1659: 1305:specific rotation 1121:James M. Sugihara 16:(Redirected from 2795: 2760: 2759: 2551:oligosaccharides 2531:Tetrasaccharides 2441: 2156:Dihydroxyacetone 2108: 2025: 2018: 2011: 2002: 1992: 1980: 1964: 1950: 1944: 1930: 1921: 1907: 1901: 1900: 1898: 1897: 1882: 1873: 1872: 1870: 1869: 1858: 1857: 1848: 1839: 1838: 1836: 1835: 1820: 1811: 1810: 1808: 1807: 1796: 1795: 1786: 1780: 1779: 1767: 1757: 1751: 1750: 1749: 1745: 1743: 1742: 1732: 1726: 1712: 1701: 1687: 1674: 1673: 1671: 1670: 1657: 1651: 1645: 1644: 1626: 1613: 1612: 1591: 1531: 1525: 1518: 1512: 1498: 1492: 1485: 1479: 1472: 1466: 1450: 1442: 1412: 1411: 1406: 1405: 1397: 1396: 1389: 1388: 1379: 1378: 1354: 1353: 1302: 1301: 1285: 1284: 1279: 1278: 1274:Closed forms of 1268:-Fructofuranose. 1267: 1266: 1259: 1250:-Fructofuranose. 1249: 1248: 1241: 1231: 1230: 1223: 1213: 1212: 1205: 1149: 1141: 1085:, in particular 1073: 1047: 1046: 1039: 1025: 1024: 1017: 1003: 1002: 995: 981: 980: 973: 957: 956: 949: 935: 934: 927: 913: 912: 905: 891: 890: 883: 873: 872: 858: 857: 850: 836: 835: 828: 814: 813: 806: 792: 791: 784: 774: 773: 746: 745: 740: 739: 642: 641: 627: 626: 621: 620: 615: 614: 610:-galactose, and 609: 608: 603: 602: 597: 596: 591: 590: 574: 573: 566: 550: 549: 542: 526: 525: 518: 502: 501: 494: 478: 477: 470: 454: 453: 446: 430: 429: 422: 406: 405: 398: 384: 383: 359: 334: 289: 288: 282:optical activity 275: 274: 269: 268: 225: 171: 163: 155: 143: 120:molecular weight 117: 66: 65: 59: 45: 44: 38: 21: 2803: 2802: 2798: 2797: 2796: 2794: 2793: 2792: 2788:Monosaccharides 2773: 2772: 2771: 2766: 2744: 2605:Oat beta-glucan 2592:Polysaccharides 2586: 2549: 2543: 2525: 2497: 2428: 2422:Neuraminic acid 2400: 2372: 2265: 2200: 2162: 2129: 2103:Monosaccharides 2097: 2066: 2035: 2029: 1973: 1968: 1967: 1951: 1947: 1931: 1924: 1908: 1904: 1895: 1893: 1884: 1883: 1876: 1867: 1865: 1855: 1854: 1850: 1849: 1842: 1833: 1831: 1822: 1821: 1814: 1805: 1803: 1793: 1792: 1788: 1787: 1783: 1776: 1759: 1758: 1754: 1747: 1740: 1739: 1734: 1733: 1729: 1713: 1704: 1693:, 6th edition. 1688: 1677: 1668: 1666: 1653: 1652: 1648: 1641: 1628: 1627: 1616: 1609: 1593: 1592: 1581: 1576: 1539: 1529: 1523: 1516: 1510: 1496: 1490: 1483: 1477: 1470: 1464: 1448: 1440: 1433: 1427: 1409: 1408: 1403: 1402: 1394: 1393: 1386: 1385: 1376: 1375: 1351: 1350: 1347: 1336: 1324: 1299: 1298: 1294: 1293: 1292: 1291: 1282: 1281: 1276: 1275: 1271: 1270: 1269: 1264: 1263: 1260: 1252: 1251: 1246: 1245: 1242: 1234: 1233: 1232:-Glucopyranose. 1228: 1227: 1224: 1216: 1215: 1214:-Glucopyranose. 1210: 1209: 1206: 1174:tetrahydrofuran 1166:tetrahydropyran 1147: 1139: 1129: 1071: 1067: 1063: 1060: 1053: 1052: 1044: 1043: 1040: 1031: 1030: 1022: 1021: 1018: 1009: 1008: 1000: 999: 996: 987: 986: 978: 977: 974: 963: 962: 954: 953: 950: 941: 940: 932: 931: 928: 919: 918: 910: 909: 906: 897: 896: 888: 887: 884: 870: 869: 864: 863: 855: 854: 851: 842: 841: 833: 832: 829: 820: 819: 811: 810: 807: 798: 797: 789: 788: 785: 771: 770: 753: 743: 742: 737: 736: 639: 638: 624: 623: 618: 617: 612: 611: 606: 605: 600: 599: 594: 593: 588: 587: 582: 581: 579: 571: 570: 567: 558: 557: 555: 547: 546: 543: 534: 533: 531: 523: 522: 519: 510: 509: 507: 499: 498: 495: 486: 485: 483: 475: 474: 471: 462: 461: 459: 451: 450: 447: 438: 437: 435: 427: 426: 423: 414: 413: 411: 403: 402: 399: 381: 380: 357: 353: 346: 341: 333: 326: 322: 318: 286: 285: 272: 271: 266: 265: 262:optical isomers 223: 213:glycosidic bond 169: 161: 153: 141: 134: 127: 116: 112: 108: 104: 85: 84: 83: 82: 74: 73: 72: 63: 62: 60: 52: 51: 42: 41: 39: 28: 23: 22: 15: 12: 11: 5: 2801: 2799: 2791: 2790: 2785: 2775: 2774: 2768: 2767: 2765: 2764: 2753: 2750: 2749: 2746: 2745: 2743: 2742: 2737: 2736: 2735: 2730: 2720: 2715: 2710: 2705: 2703:Levan beta 2→6 2700: 2695: 2694: 2693: 2677: 2666: 2665: 2664: 2648: 2639: 2634: 2633: 2632: 2627: 2622: 2617: 2612: 2607: 2596: 2594: 2588: 2587: 2585: 2584: 2579: 2573: 2567: 2561: 2555: 2553: 2545: 2544: 2542: 2541: 2535: 2533: 2527: 2526: 2524: 2523: 2518: 2513: 2507: 2505: 2503:Trisaccharides 2499: 2498: 2496: 2495: 2490: 2485: 2480: 2475: 2470: 2465: 2460: 2455: 2449: 2447: 2438: 2434: 2433: 2430: 2429: 2427: 2426: 2425: 2424: 2414: 2408: 2406: 2402: 2401: 2399: 2398: 2397: 2396: 2391: 2389:Mannoheptulose 2382: 2380: 2374: 2373: 2371: 2370: 2369: 2368: 2363: 2358: 2350: 2349: 2348: 2343: 2338: 2333: 2323: 2322: 2321: 2316: 2311: 2306: 2301: 2296: 2291: 2286: 2275: 2273: 2267: 2266: 2264: 2263: 2262: 2261: 2251: 2250: 2249: 2244: 2236: 2235: 2234: 2229: 2224: 2219: 2210: 2208: 2202: 2201: 2199: 2198: 2197: 2196: 2188: 2187: 2186: 2181: 2172: 2170: 2164: 2163: 2161: 2160: 2159: 2158: 2150: 2149: 2148: 2146:Glyceraldehyde 2139: 2137: 2131: 2130: 2128: 2127: 2126: 2125: 2123:Glycolaldehyde 2116: 2114: 2105: 2099: 2098: 2096: 2095: 2090: 2085: 2080: 2074: 2072: 2068: 2067: 2065: 2064: 2059: 2054: 2049: 2043: 2041: 2037: 2036: 2030: 2028: 2027: 2020: 2013: 2005: 1999: 1998: 1986: 1972: 1971:External links 1969: 1966: 1965: 1945: 1922: 1902: 1874: 1840: 1812: 1781: 1774: 1752: 1727: 1702: 1675: 1646: 1639: 1614: 1607: 1578: 1577: 1575: 1572: 1571: 1570: 1565: 1560: 1555: 1550: 1545: 1538: 1535: 1534: 1533: 1520: 1507: 1487: 1474: 1455:-deoxy-", the 1443:) replaced by 1426: 1423: 1400:ascorbic acid. 1346: 1343: 1334: 1323: 1320: 1273: 1272: 1261: 1254: 1253: 1243: 1236: 1235: 1225: 1218: 1217: 1207: 1200: 1199: 1198: 1197: 1196: 1128: 1125: 1117:George U. Yuen 1059: 1056: 1055: 1054: 1041: 1034: 1032: 1019: 1012: 1010: 997: 990: 988: 975: 968: 965: 964: 951: 944: 942: 929: 922: 920: 907: 900: 898: 885: 878: 866: 865: 852: 845: 843: 830: 823: 821: 808: 801: 799: 786: 779: 775:-isomers are: 752: 749: 698: 697: 645:binary numbers 616:-mannose. The 584: 583: 568: 561: 559: 544: 537: 535: 520: 513: 511: 496: 489: 487: 472: 465: 463: 448: 441: 439: 424: 417: 415: 400: 393: 369:chiral centres 354:H−C(=O)−(CHOH) 345: 342: 340: 339:Classification 337: 294:by animals or 97:monosaccharide 76: 75: 61: 54: 53: 40: 33: 32: 31: 30: 29: 26: 24: 14: 13: 10: 9: 6: 4: 3: 2: 2800: 2789: 2786: 2784: 2781: 2780: 2778: 2763: 2755: 2754: 2751: 2741: 2738: 2734: 2731: 2729: 2726: 2725: 2724: 2721: 2719: 2716: 2714: 2711: 2709: 2706: 2704: 2701: 2699: 2698:Hemicellulose 2696: 2692: 2689: 2688: 2687: 2686: 2682: 2678: 2676: 2675: 2671: 2667: 2663: 2660: 2659: 2658: 2657: 2653: 2649: 2647: 2643: 2640: 2638: 2635: 2631: 2628: 2626: 2623: 2621: 2618: 2616: 2613: 2611: 2608: 2606: 2603: 2602: 2601: 2598: 2597: 2595: 2593: 2589: 2583: 2580: 2577: 2574: 2571: 2568: 2565: 2562: 2560: 2557: 2556: 2554: 2552: 2546: 2540: 2537: 2536: 2534: 2532: 2528: 2522: 2519: 2517: 2514: 2512: 2509: 2508: 2506: 2504: 2500: 2494: 2491: 2489: 2486: 2484: 2481: 2479: 2476: 2474: 2471: 2469: 2466: 2464: 2461: 2459: 2456: 2454: 2451: 2450: 2448: 2446: 2445:Disaccharides 2442: 2439: 2435: 2423: 2420: 2419: 2418: 2415: 2413: 2410: 2409: 2407: 2403: 2395: 2394:Sedoheptulose 2392: 2390: 2387: 2386: 2385:Ketoheptoses 2384: 2383: 2381: 2379: 2375: 2367: 2364: 2362: 2359: 2357: 2354: 2353: 2352:Deoxy sugars 2351: 2347: 2344: 2342: 2339: 2337: 2334: 2332: 2329: 2328: 2327: 2324: 2320: 2317: 2315: 2312: 2310: 2307: 2305: 2302: 2300: 2297: 2295: 2292: 2290: 2287: 2285: 2282: 2281: 2280: 2277: 2276: 2274: 2272: 2268: 2260: 2257: 2256: 2255: 2252: 2248: 2245: 2243: 2240: 2239: 2238:Ketopentoses 2237: 2233: 2230: 2228: 2225: 2223: 2220: 2218: 2215: 2214: 2213:Aldopentoses 2212: 2211: 2209: 2207: 2203: 2195: 2192: 2191: 2189: 2185: 2182: 2180: 2177: 2176: 2175:Aldotetroses 2174: 2173: 2171: 2169: 2165: 2157: 2154: 2153: 2151: 2147: 2144: 2143: 2141: 2140: 2138: 2136: 2132: 2124: 2121: 2120: 2118: 2117: 2115: 2113: 2109: 2106: 2104: 2100: 2094: 2091: 2089: 2086: 2084: 2081: 2079: 2076: 2075: 2073: 2069: 2063: 2060: 2058: 2055: 2053: 2050: 2048: 2045: 2044: 2042: 2038: 2034: 2033:carbohydrates 2026: 2021: 2019: 2014: 2012: 2007: 2006: 2003: 1996: 1991: 1987: 1984: 1979: 1975: 1974: 1970: 1963: 1959: 1955: 1949: 1946: 1943: 1939: 1935: 1929: 1927: 1923: 1920: 1916: 1912: 1906: 1903: 1892: 1888: 1881: 1879: 1875: 1864: 1860: 1847: 1845: 1841: 1830: 1826: 1819: 1817: 1813: 1802: 1798: 1785: 1782: 1777: 1771: 1766: 1765: 1756: 1753: 1737: 1731: 1728: 1725: 1721: 1717: 1711: 1709: 1707: 1703: 1700: 1699:9780138924645 1696: 1692: 1686: 1684: 1682: 1680: 1676: 1665: 1661: 1650: 1647: 1642: 1640:0-387-94951-8 1636: 1632: 1625: 1623: 1621: 1619: 1615: 1610: 1608:3-527-31528-4 1604: 1600: 1596: 1590: 1588: 1586: 1584: 1580: 1573: 1569: 1566: 1564: 1561: 1559: 1556: 1554: 1551: 1549: 1546: 1544: 1541: 1540: 1536: 1527: 1521: 1514: 1508: 1505: 1502: 1494: 1488: 1481: 1475: 1468: 1462: 1461: 1460: 1458: 1454: 1446: 1438: 1432: 1424: 1422: 1420: 1416: 1401: 1391: 1383: 1373: 1369: 1365: 1360: 1358: 1344: 1342: 1341:in solution. 1340: 1333: 1328: 1321: 1319: 1317: 1312: 1308: 1306: 1289: 1280:-glucose and 1258: 1240: 1222: 1204: 1195: 1193: 1192:chiral center 1188: 1186: 1182: 1177: 1175: 1171: 1167: 1164: 1160: 1155: 1153: 1145: 1136: 1134: 1126: 1124: 1122: 1118: 1114: 1112: 1106: 1104: 1100: 1096: 1092: 1088: 1084: 1080: 1079:unfermentable 1075: 1068:−C(=O)−(CHOH) 1058:3-Ketohexoses 1057: 1051: 1038: 1033: 1029: 1016: 1011: 1007: 994: 989: 985: 972: 967: 961: 948: 943: 939: 926: 921: 917: 904: 899: 895: 882: 877: 875: 862: 849: 844: 840: 827: 822: 818: 805: 800: 796: 783: 778: 776: 767: 764: 762: 758: 750: 748: 733: 731: 727: 723: 719: 715: 711: 707: 703: 700:referring to 695: 691: 687: 683: 679: 675: 671: 668: 665: 664: 663: 661: 657: 652: 650: 646: 635: 633: 632: 578: 565: 560: 554: 541: 536: 530: 517: 512: 506: 493: 488: 482: 469: 464: 458: 445: 440: 434: 421: 416: 410: 397: 392: 390: 388: 378: 374: 373:stereoisomers 370: 365: 363: 351: 343: 338: 336: 332: 316: 312: 308: 303: 301: 297: 293: 283: 279: 263: 259: 258:stereoisomers 254: 252: 250: 245: 241: 237: 233: 229: 221: 216: 214: 210: 206: 202: 198: 194: 190: 186: 182: 177: 175: 167: 164:), forming a 159: 151: 147: 140: 135:−C(=O)−(CHOH) 132: 123: 121: 102: 98: 94: 90: 80: 70: 58: 49: 37: 19: 2679: 2668: 2650: 2582:Maltodextrin 2463:Isomaltulose 2270: 2254:Deoxy sugars 2190:Ketotetrose 2093:Mutarotation 1953: 1948: 1933: 1910: 1905: 1894:. Retrieved 1890: 1866:. Retrieved 1862: 1832:. Retrieved 1828: 1804:. Retrieved 1800: 1784: 1763: 1755: 1730: 1715: 1690: 1667:. Retrieved 1663: 1649: 1630: 1598: 1456: 1452: 1434: 1425:Deoxyhexoses 1392: 1361: 1348: 1331: 1329: 1325: 1316:mutarotation 1313: 1309: 1295: 1189: 1178: 1163:cyclic ether 1161:, after the 1156: 1144:ether bridge 1137: 1130: 1127:Cyclic forms 1110: 1107: 1102: 1098: 1090: 1077:In 1897, an 1076: 1061: 867: 768: 765: 754: 734: 729: 725: 721: 717: 713: 709: 705: 701: 699: 693: 689: 685: 681: 677: 673: 669: 666: 656:Emil Fischer 654:The chemist 653: 636: 629: 585: 366: 347: 330: 307:deoxyhexoses 306: 304: 255: 248: 247: 239: 227: 220:formyl group 217: 181:biochemistry 178: 145: 138: 130: 124: 118:, and their 92: 86: 2740:Xanthan gum 2728:Amylopectin 2600:Beta-glucan 2511:Maltotriose 2326:Ketohexoses 2279:Aldohexoses 2259:Deoxyribose 2194:Erythrulose 2152:Ketotriose 2142:Aldotriose 1995:Ketohexoses 1983:Aldohexoses 1473:-galactose) 1431:Deoxy sugar 1339:aldohexoses 1113:-3-hexulose 1095:portmanteau 751:Ketohexoses 377:enantiomers 344:Aldohexoses 292:metabolized 251:-ketohexose 158:single bond 2777:Categories 2516:Melezitose 2458:Isomaltose 2453:Cellobiose 2119:Aldodiose 1896:2018-04-26 1887:"Tagatose" 1868:2018-04-26 1853:"Sorbose, 1834:2018-04-26 1825:"Fructose" 1806:2018-04-26 1669:2018-04-26 1574:References 1532:-tagatose) 1501:sulfolipid 1493:-Quinovose 1429:See also: 1181:hemiacetal 604:-glucose, 309:, such as 240:ketohexose 228:aldohexose 201:glycosides 2670:Galactose 2625:Cellulose 2615:Sizofiran 2539:Stachyose 2521:Raffinose 2488:Trehalose 2473:Lactulose 2294:Galactose 2217:Arabinose 2179:Erythrose 2031:Types of 1885:Pubchem. 1851:Pubchem. 1823:Pubchem. 1797:-Psicose" 1789:Pubchem. 1768:. Wiley. 1660:-Psicose" 1654:Pubchem. 1528:(6-deoxy- 1526:-Fuculose 1515:(6-deoxy- 1513:-Pneumose 1495:(6-deoxy- 1486:-mannose) 1482:(6-deoxy- 1480:-Rhamnose 1469:(6-deoxy- 1437:hydroxyls 1390:-isomer. 1185:hemiketal 586:Of these 553:Galactose 296:fermented 197:cellulose 89:chemistry 2762:Category 2691:Glycogen 2674:Galactan 2652:Fructose 2637:Chitosan 2610:Lentinan 2559:Acarbose 2493:Turanose 2437:Multiple 2378:Heptoses 2366:Rhamnose 2361:Fuculose 2346:Tagatose 2331:Fructose 2247:Xylulose 2242:Ribulose 2206:Pentoses 2168:Tetroses 2071:Geometry 2062:Pyranose 2057:Furanose 1597:(2007). 1537:See also 1519:-talose) 1445:hydrogen 1415:Fructose 1372:tagatose 1368:fructose 1170:furanose 1159:pyranose 1103:fructose 1064:H−(CHOH) 1050:Tagatose 1006:Fructose 960:Tagatose 916:Fructose 861:Tagatose 817:Fructose 761:fructose 728:actose, 660:mnemonic 350:aldehyde 315:rhamnose 205:dihexose 189:fructose 174:hydrogen 166:carbonyl 150:hydroxyl 144:, where 128:H−(CHOH) 69:Fructose 18:C6 sugar 2783:Hexoses 2733:Amylose 2681:Glucose 2656:Fructan 2646:Dextran 2642:Dextrin 2620:Zymosan 2483:Sucrose 2478:Maltose 2468:Lactose 2417:Nonoses 2412:Octoses 2405:Above 7 2341:Sorbose 2336:Psicose 2314:Mannose 2299:Glucose 2289:Altrose 2271:Hexoses 2184:Threose 2135:Trioses 2040:General 1563:Heptose 1558:Pentose 1553:Tetrose 1467:-Fucose 1447:atoms ( 1419:sucrose 1382:sorbose 1364:psicose 1357:glucose 1099:glucose 1091:glutose 1028:Sorbose 984:Psicose 938:Sorbose 894:Psicose 839:Sorbose 795:Psicose 716:nnose, 712:ucose, 481:Mannose 457:Glucose 433:Altrose 362:glucose 270:-" or " 209:sucrose 185:glucose 168:group ( 48:Glucose 2723:Starch 2718:Pectin 2713:Mannan 2708:Lignin 2685:Glucan 2662:Inulin 2630:Chitin 2356:Fucose 2319:Talose 2304:Gulose 2284:Allose 2232:Xylose 2227:Ribose 2222:Lyxose 2112:Dioses 2088:Epimer 2078:Anomer 2052:Ketose 2047:Aldose 1772:  1748:  1697:  1637:  1605:  1568:Octose 1548:Triose 1506:(SQDG) 1152:oxygen 757:ketone 732:lose. 724:dose, 720:lose, 672:uists 577:Talose 505:Gulose 409:Allose 389:, are 311:fucose 300:yeasts 244:ketose 236:ketone 232:aldose 207:(like 199:, and 193:starch 101:carbon 93:hexose 2578:(IMO) 2572:(GOS) 2566:(FOS) 2548:Other 2309:Idose 1543:Diose 1083:bases 708:ose, 704:ose, 676:adly 529:Idose 224:−CH=O 95:is a 1770:ISBN 1695:ISBN 1635:ISBN 1603:ISBN 1370:and 1119:and 1111:xylo 1101:and 1093:, a 706:altr 696:nks. 692:lon 670:altr 649:bits 313:and 187:and 91:, a 1958:doi 1938:doi 1915:doi 1720:doi 1441:−OH 1148:−O− 1097:of 726:gal 702:all 690:gal 680:ke 667:All 580:111 556:110 532:101 508:100 484:011 460:010 436:001 412:000 298:by 170:C=O 154:−OH 87:In 2779:: 2683:/ 2672:/ 2654:/ 2644:/ 1925:^ 1889:. 1877:^ 1861:. 1859:-" 1843:^ 1827:. 1815:^ 1799:. 1705:^ 1678:^ 1662:. 1617:^ 1582:^ 1449:−H 1366:, 1318:. 1262:β- 1244:α- 1226:β- 1208:α- 1140:=O 1123:. 1072:−H 763:. 730:ta 718:gu 714:ma 710:gl 694:ta 688:n 684:m 682:gu 678:ma 674:gl 634:. 364:. 358:−H 329:6− 325:12 302:. 215:. 195:, 162:=O 142:−H 137:6− 133:−1 111:12 2024:e 2017:t 2010:v 1960:: 1940:: 1917:: 1899:. 1871:. 1856:D 1837:. 1809:. 1794:D 1791:" 1778:. 1741:L 1722:: 1672:. 1658:D 1656:" 1643:. 1611:. 1530:L 1524:L 1517:L 1511:L 1497:D 1491:D 1484:L 1478:L 1471:L 1465:L 1457:x 1453:x 1439:( 1413:- 1410:D 1404:D 1395:D 1387:L 1377:D 1355:- 1352:D 1335:a 1332:K 1300:D 1290:. 1283:D 1277:D 1265:D 1247:D 1229:D 1211:D 1146:( 1070:3 1066:2 1048:- 1045:L 1026:- 1023:L 1004:- 1001:L 982:- 979:L 958:- 955:D 936:- 933:D 914:- 911:D 892:- 889:D 871:L 859:- 856:D 837:- 834:D 815:- 812:D 793:- 790:D 772:D 744:D 738:L 722:i 686:i 640:D 625:L 619:L 613:D 607:D 601:D 595:D 589:D 575:- 572:D 551:- 548:D 527:- 524:D 503:- 500:D 479:- 476:D 455:- 452:D 431:- 428:D 407:- 404:D 382:D 356:5 331:y 327:O 323:H 321:6 319:C 287:D 273:L 267:D 249:n 222:( 146:n 139:n 131:n 115:6 113:O 109:H 107:6 105:C 81:. 71:. 67:- 64:D 50:. 46:- 43:D 20:)

Index

C6 sugar

Glucose

Fructose
Fischer projection
chemistry
monosaccharide
carbon
molecular weight
hydroxyl
single bond
carbonyl
hydrogen
biochemistry
glucose
fructose
starch
cellulose
glycosides
dihexose
sucrose
glycosidic bond
formyl group
aldose
ketone
ketose
stereoisomers
optical isomers
Fischer projection

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