1228:
1246:
1192:
1210:
529:
1735:
837:
2747:
433:
409:
815:
771:
553:
481:
385:
25:
892:
505:
793:
46:
1026:
982:
1979:
1967:
457:
960:
914:
936:
1004:
870:
1315:
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.
1299:
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.
1285:
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,
1183:, 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".
114:
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
1120:
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
1303:
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
640:, 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.
755:
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.
758:
In the linear form, the 2-ketohexoses have three chiral centers and therefore eight possible stereoisomers (2), comprising four pairs of enantiomers. The four
1109:
1098:
651:
device for remembering the order given above, which corresponds to the configurations about the chiral centers when ordered as 3-bit binary strings:
242:. However, the 3-ketohexoses have not been observed in nature, and are difficult to synthesize; so the term "ketohexose" usually means 2-ketohexose.
1105:
1172:
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
1168:
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
1941:
Akira Sera (1962): "Studies on the
Chemical Decomposition of Simple Sugars. XIII. Separation of the So-called Glutose (a 3-Ketohexose)".
1478:
1094:, and was claimed to be a 3-ketohexose. However, subsequent studies showed that the substance was a mixture of various other compounds.
1498:
1296:
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.
1898:
C. A. Lobry de Bruyn and W. Alberda van
Ekenstein (1897): "Action des alcalis sur les sucres. VI: La glutose et la pseudo‐fructose".
2011:
1762:
863:
forms have the hydroxyls on carbons 3, 4,and 5 reversed. Below are depiction of the eight isomers in an alternative style:
1733:-altrose", issued 1990-10-30, assigned to Government of the United States of America, Secretary of Agriculture
1687:
1627:
1595:
1388:
1779:
1644:
337:
The aldohexoses are a subclass of the hexoses which, in the linear form, have the carbonyl at carbon 1, forming an
324:
that can be described as derived from hexoses by replacement of one or more hydroxyl groups with hydrogen atoms.
269:
of the molecule, is to the right or to the left of the axis, respectively. These labels are independent of the
1492:
1983:
1971:
748:-containing hexose. The important ketohexoses are the 2-ketohexoses, and the most important 2-ketose is
2004:
1051:
In theory, the ketohexoses include also the 3-ketohexoses, which have the carbonyl in position 3; namely
1165:. The conventional numbering of the carbons in the closed form is the same as in the open-chain form.
1724:
253:. Each pair has a conventional name (like "glucose" or "fructose"), and the two members are labeled "
619:
2776:
2071:
1157:, that has the same ring. If the cycle has four carbon atoms (five in total), the form is called
2564:
1921:
George L. Clark, Hung Kao, Louis
Sattler, and F. W. Zerban (1949): "Chemical Nature of Glutose".
1121:
2750:
2558:
1997:
1841:
1063:. However, these compounds are not known to occur in nature, and are difficult to synthesize.
1875:
165:
atoms. The carbons are commonly numbered 1 to 6 starting at the end closest to the carbonyl.
2552:
1813:
528:
1448:
indicating the carbon with the affected hydroxyl. Some examples of biological interest are
1424:
The term "hexose" may sometimes be used to include the deoxyhexoses, which have one or more
249:
that differ in the spatial position of the hydroxyl groups. These species occur in pairs of
2691:
644:
273:
of the isomers. In general, only one of the two enantiomers occurs naturally (for example,
8:
432:
408:
1751:
1276:
1075:
836:
552:
480:
384:
375:
266:
67:
891:
1758:
1683:
1623:
1591:
1293:
1146:
If the cycle has five carbon atoms (six atoms in total), the closed form is called a
814:
770:
504:
2771:
2144:
1946:
1926:
1903:
1708:
1583:
1396:-Tagatose is a rare natural ketohexose that is found in small quantities in food.
1071:
270:
108:
2593:
2539:
2519:
2410:
1162:
1154:
201:
1227:
1025:
981:
792:
456:
223:. Otherwise, if the carbonyl position is 2 or 3, the sugar is a derivative of a
2580:
2377:
2134:
2111:
2091:
1425:
1326:
of 10.28, will only deprotonate at high pH, so are marginally less stable than
1245:
1191:
250:
85:
1406:
is responsible for the sweet taste of many fruits, and is a building block of
1209:
959:
935:
913:
2765:
2686:
2603:
2491:
2382:
1907:
633:
357:
1003:
869:
2570:
2451:
2433:
2081:
2021:
1304:
1180:
1067:
361:
284:
246:
208:
193:
169:
2728:
2716:
2588:
2499:
2247:
2242:
2182:
1989:
1950:
1419:
1132:
1083:
146:
1930:
1712:
2504:
2446:
2441:
2314:
2267:
1489:
1327:
1169:
636:
from 0 to 7, namely 000, 001, 010, 011, 100, 101, 110, 111. The three
365:
280:
736:-isomers; with all hydroxyls reversed, including the one on carbon 5.
245:
In the linear form, there are 16 aldohexoses and eight 2-ketohexoses,
2662:
2658:
2613:
2527:
2509:
2476:
2461:
2282:
2205:
2167:
1173:
541:
189:
185:
77:
1348:, which is the main "fuel" for metabolism in many living organisms.
2679:
2640:
2625:
2598:
2547:
2481:
2354:
2349:
2334:
2319:
2235:
2230:
2050:
2045:
1511:
1465:
1433:
1403:
1360:
1356:
1319:
2-Ketohexoses are stable over a wide pH range, and with a primary p
1158:
1147:
1038:
994:
948:
904:
849:
805:
749:
648:
338:
303:
177:
162:
154:
138:
57:
24:
161:). The remaining bonds of the carbon atoms are satisfied by seven
2721:
2701:
2669:
2644:
2634:
2630:
2608:
2471:
2466:
2456:
2366:
2329:
2324:
2302:
2287:
2277:
2194:
2172:
2156:
1551:
1546:
1541:
1407:
1370:
1352:
1345:
1016:
972:
926:
882:
827:
783:
469:
445:
421:
350:
197:
173:
36:
1104:, through a rather complex route, was first reported in 1961 by
2711:
2706:
2696:
2673:
2650:
2618:
2405:
2400:
2344:
2307:
2292:
2272:
2220:
2215:
2210:
2123:
2076:
2066:
2040:
2035:
1978:
1966:
1556:
1536:
1452:
1140:
745:
587:-altrose occur in living organisms, but only three are common:
565:
493:
397:
299:
232:
224:
220:
181:
89:
1139:) between the two carbon atoms, thus creating a ring with one
2297:
2100:
1531:
1151:
517:
288:
45:
1900:
Recueil des
Travaux Chimiques des Pays-Bas et de la Belgique
611:-isomers are generally absent in living organisms; however,
265:-", depending on whether the hydroxyl in position 5, in the
1124:
between the carbonyl group and one of the hydroxyl groups.
1097:
The unequivocal synthesis and isolation of a 3-ketohexose,
1678:
Robert
Thornton Morrison and Robert Neilson Boyd (1998):
1387:-Sorbose is commonly used in the commercial synthesis of
1338:
The aldohexose that is most important in biochemistry is
637:
626:
When drawn in this order, the
Fischer projections of the
617:-altrose has been isolated from strains of the bacterium
730:-aldohexoses are the mirror images of the corresponding
137:
is 1, 2, 3, 4, 5. Namely, five of the carbons have one
1440:). It is named as the parent hexose, with the prefix "
1727:, Stack; Robert J., "Microbial production of
1588:
180:) and as building blocks of other compounds such as
1582:
1750:
294:The term "hexose" sometimes is assumed to include
1703:George U. Yuen and James M. Sugihara (1961): "".
2763:
1723:
1131:group into a hydroxyl, and the hydroxyl into an
632:-aldohexoses can be identified with the 3-digit
92:atoms. The chemical formula for all hexoses is
1869:
1867:
1070:product obtained by treatment of fructose with
207:When the carbonyl is in position 1, forming an
1835:
1833:
1807:
1805:
1333:
2005:
1748:
1617:
1179:The closure turns the carboxyl carbon into a
1917:
1915:
1864:
1771:
200:) by a condensation reaction that makes 1,6-
1830:
1802:
1613:
1611:
1609:
1607:
2019:
2012:
1998:
1699:
1697:
1695:
1674:
1672:
1670:
1668:
1578:
1576:
1574:
1572:
1943:Bulletin of the Chemical Society of Japan
1912:
1892:
1945:, volume 35, issue 12, pages 2031-2033.
1935:
1604:
1742:
1707:, volume 26, issue 5, pages 1598-1601.
1692:
1665:
1569:
356:In linear form, an aldohexose has four
172:, both as isolated molecules (such as
2764:
1923:Industrial & Engineering Chemistry
1310:
647:is said to have devised the following
1993:
1925:, volume 41, issue 3, pages 530-533.
1902:, volume 16, issue 9, pages 274-281.
1292:-glucose forms an α crystal that has
1620:Essentials of Carbohydrate Chemistry
360:, which give 16 possible aldohexose
1873:
1839:
1811:
1777:
1753:The vocabulary of organic chemistry
1642:
168:Hexoses are extremely important in
13:
724:The Fischer diagrams of the eight
14:
2788:
1959:
1636:
368:. The linear forms of the eight
349:. The most important example is
327:
306:: compounds with general formula
2746:
2745:
1977:
1965:
1488:-glucose), found as part of the
1244:
1226:
1208:
1190:
1046:
1024:
1002:
980:
958:
934:
912:
890:
868:
835:
813:
791:
769:
551:
527:
503:
479:
455:
431:
407:
383:
44:
23:
1413:
1143:atom and four or five carbons.
1115:
1717:
1493:sulfoquinovosyl diacylglycerol
739:
332:
66:Two important hexoses, in the
1:
1562:
1031:
1009:
987:
965:
941:
919:
897:
875:
842:
820:
798:
776:
558:
534:
510:
486:
462:
438:
414:
390:
1705:Journal of Organic Chemistry
149:, and one has an oxo group (
7:
1749:Milton Orchin, ed. (1980).
1525:
1334:Natural occurrence and uses
1176:with a five-membered ring.
10:
2793:
1417:
364:(2),comprising 8 pairs of
341:derivative with structure
215:), the sugar is called an
2741:
2579:
2536:
2518:
2490:
2432:
2425:
2393:
2365:
2258:
2193:
2155:
2122:
2099:
2090:
2059:
2028:
1590:(1 ed.). Wiley-VCH.
620:Butyrivibrio fibrisolvens
2072:Cyclohexane conformation
1908:10.1002/recl.18970160903
1880:pubchem.ncbi.nlm.nih.gov
1852:pubchem.ncbi.nlm.nih.gov
1818:pubchem.ncbi.nlm.nih.gov
1790:pubchem.ncbi.nlm.nih.gov
1653:pubchem.ncbi.nlm.nih.gov
1622:(1 ed.). Springer.
1373:occurs naturally as the
145:) each, connected by a
88:(simple sugar) with six
2565:Isomaltooligosaccharide
1363:occur naturally as the
1127:The reaction turns the
2559:Galactooligosaccharide
1618:John F. Robyt (1997).
1122:internal rearrangement
2553:Fructooligosaccharide
1725:US patent 4966845
1078:, was given the name
581:-isomers, all except
374:-aldohexoses, in the
279:-glucose) and can be
16:6-carbon simple sugar
1986:at Wikimedia Commons
1974:at Wikimedia Commons
1951:10.1246/bcsj.35.2031
1410:, the common sugar.
231:, a special case of
219:, a special case of
192:. Hexoses can form
1931:10.1021/ie50471a020
1713:10.1021/jo01064a070
1584:Thisbe K. Lindhorst
1311:Chemical properties
1161:after the compound
235:; specifically, an
1369:-isomers, whereas
1351:The 2-ketohexoses
1277:Haworth projection
1275:-fructose, in the
1076:lead(II) hydroxide
857:The corresponding
744:A ketohexose is a
376:Fischer projection
267:Fischer projection
227:, and is called a
141:functional group (
111:is 180.156 g/mol.
68:Fischer projection
2759:
2758:
2737:
2736:
2421:
2420:
1982:Media related to
1970:Media related to
1764:978-0-471-04491-8
1680:Organic Chemistry
1648:
1294:specific rotation
1110:James M. Sugihara
2784:
2749:
2748:
2540:oligosaccharides
2520:Tetrasaccharides
2430:
2429:
2145:Dihydroxyacetone
2097:
2096:
2014:
2007:
2000:
1991:
1990:
1981:
1969:
1953:
1939:
1933:
1919:
1910:
1896:
1890:
1889:
1887:
1886:
1871:
1862:
1861:
1859:
1858:
1847:
1846:
1837:
1828:
1827:
1825:
1824:
1809:
1800:
1799:
1797:
1796:
1785:
1784:
1775:
1769:
1768:
1756:
1746:
1740:
1739:
1738:
1734:
1732:
1731:
1721:
1715:
1701:
1690:
1676:
1663:
1662:
1660:
1659:
1646:
1640:
1634:
1633:
1615:
1602:
1601:
1580:
1520:
1514:
1507:
1501:
1487:
1481:
1474:
1468:
1461:
1455:
1439:
1431:
1401:
1400:
1395:
1394:
1386:
1385:
1378:
1377:
1368:
1367:
1343:
1342:
1291:
1290:
1274:
1273:
1268:
1267:
1263:Closed forms of
1257:-Fructofuranose.
1256:
1255:
1248:
1239:-Fructofuranose.
1238:
1237:
1230:
1220:
1219:
1212:
1202:
1201:
1194:
1138:
1130:
1074:, in particular
1062:
1036:
1035:
1028:
1014:
1013:
1006:
992:
991:
984:
970:
969:
962:
946:
945:
938:
924:
923:
916:
902:
901:
894:
880:
879:
872:
862:
861:
847:
846:
839:
825:
824:
817:
803:
802:
795:
781:
780:
773:
763:
762:
735:
734:
729:
728:
631:
630:
616:
615:
610:
609:
604:
603:
599:-galactose, and
598:
597:
592:
591:
586:
585:
580:
579:
563:
562:
555:
539:
538:
531:
515:
514:
507:
491:
490:
483:
467:
466:
459:
443:
442:
435:
419:
418:
411:
395:
394:
387:
373:
372:
348:
323:
278:
277:
271:optical activity
264:
263:
258:
257:
214:
160:
152:
144:
132:
109:molecular weight
106:
55:
54:
48:
34:
33:
27:
2792:
2791:
2787:
2786:
2785:
2783:
2782:
2781:
2777:Monosaccharides
2762:
2761:
2760:
2755:
2733:
2594:Oat beta-glucan
2581:Polysaccharides
2575:
2538:
2532:
2514:
2486:
2417:
2411:Neuraminic acid
2389:
2361:
2254:
2189:
2151:
2118:
2092:Monosaccharides
2086:
2055:
2024:
2018:
1962:
1957:
1956:
1940:
1936:
1920:
1913:
1897:
1893:
1884:
1882:
1872:
1865:
1856:
1854:
1844:
1843:
1838:
1831:
1822:
1820:
1810:
1803:
1794:
1792:
1782:
1781:
1776:
1772:
1765:
1747:
1743:
1736:
1729:
1728:
1722:
1718:
1702:
1693:
1682:, 6th edition.
1677:
1666:
1657:
1655:
1641:
1637:
1630:
1616:
1605:
1598:
1581:
1570:
1565:
1528:
1518:
1512:
1505:
1499:
1485:
1479:
1472:
1466:
1459:
1453:
1437:
1429:
1422:
1416:
1398:
1397:
1392:
1391:
1383:
1382:
1375:
1374:
1365:
1364:
1340:
1339:
1336:
1325:
1313:
1288:
1287:
1283:
1282:
1281:
1280:
1271:
1270:
1265:
1264:
1260:
1259:
1258:
1253:
1252:
1249:
1241:
1240:
1235:
1234:
1231:
1223:
1222:
1221:-Glucopyranose.
1217:
1216:
1213:
1205:
1204:
1203:-Glucopyranose.
1199:
1198:
1195:
1163:tetrahydrofuran
1155:tetrahydropyran
1136:
1128:
1118:
1060:
1056:
1052:
1049:
1042:
1041:
1033:
1032:
1029:
1020:
1019:
1011:
1010:
1007:
998:
997:
989:
988:
985:
976:
975:
967:
966:
963:
952:
951:
943:
942:
939:
930:
929:
921:
920:
917:
908:
907:
899:
898:
895:
886:
885:
877:
876:
873:
859:
858:
853:
852:
844:
843:
840:
831:
830:
822:
821:
818:
809:
808:
800:
799:
796:
787:
786:
778:
777:
774:
760:
759:
742:
732:
731:
726:
725:
628:
627:
613:
612:
607:
606:
601:
600:
595:
594:
589:
588:
583:
582:
577:
576:
571:
570:
568:
560:
559:
556:
547:
546:
544:
536:
535:
532:
523:
522:
520:
512:
511:
508:
499:
498:
496:
488:
487:
484:
475:
474:
472:
464:
463:
460:
451:
450:
448:
440:
439:
436:
427:
426:
424:
416:
415:
412:
403:
402:
400:
392:
391:
388:
370:
369:
346:
342:
335:
330:
322:
315:
311:
307:
275:
274:
261:
260:
255:
254:
251:optical isomers
212:
202:glycosidic bond
158:
150:
142:
130:
123:
116:
105:
101:
97:
93:
74:
73:
72:
71:
63:
62:
61:
52:
51:
49:
41:
40:
31:
30:
28:
17:
12:
11:
5:
2790:
2780:
2779:
2774:
2757:
2756:
2754:
2753:
2742:
2739:
2738:
2735:
2734:
2732:
2731:
2726:
2725:
2724:
2719:
2709:
2704:
2699:
2694:
2692:Levan beta 2→6
2689:
2684:
2683:
2682:
2666:
2655:
2654:
2653:
2637:
2628:
2623:
2622:
2621:
2616:
2611:
2606:
2601:
2596:
2585:
2583:
2577:
2576:
2574:
2573:
2568:
2562:
2556:
2550:
2544:
2542:
2534:
2533:
2531:
2530:
2524:
2522:
2516:
2515:
2513:
2512:
2507:
2502:
2496:
2494:
2492:Trisaccharides
2488:
2487:
2485:
2484:
2479:
2474:
2469:
2464:
2459:
2454:
2449:
2444:
2438:
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2423:
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2413:
2403:
2397:
2395:
2391:
2390:
2388:
2387:
2386:
2385:
2380:
2378:Mannoheptulose
2371:
2369:
2363:
2362:
2360:
2359:
2358:
2357:
2352:
2347:
2339:
2338:
2337:
2332:
2327:
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2312:
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2300:
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2275:
2264:
2262:
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2253:
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2251:
2250:
2240:
2239:
2238:
2233:
2225:
2224:
2223:
2218:
2213:
2208:
2199:
2197:
2191:
2190:
2188:
2187:
2186:
2185:
2177:
2176:
2175:
2170:
2161:
2159:
2153:
2152:
2150:
2149:
2148:
2147:
2139:
2138:
2137:
2135:Glyceraldehyde
2128:
2126:
2120:
2119:
2117:
2116:
2115:
2114:
2112:Glycolaldehyde
2105:
2103:
2094:
2088:
2087:
2085:
2084:
2079:
2074:
2069:
2063:
2061:
2057:
2056:
2054:
2053:
2048:
2043:
2038:
2032:
2030:
2026:
2025:
2017:
2016:
2009:
2002:
1994:
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1960:External links
1958:
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1911:
1891:
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1527:
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1523:
1522:
1509:
1496:
1476:
1463:
1444:-deoxy-", the
1432:) replaced by
1415:
1412:
1389:ascorbic acid.
1335:
1332:
1323:
1312:
1309:
1262:
1261:
1250:
1243:
1242:
1232:
1225:
1224:
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1114:
1106:George U. Yuen
1058:
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797:
790:
788:
775:
768:
764:-isomers are:
741:
738:
687:
686:
634:binary numbers
605:-mannose. The
573:
572:
557:
550:
548:
533:
526:
524:
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500:
485:
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476:
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413:
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389:
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358:chiral centres
344:
343:H−C(=O)−(CHOH)
334:
331:
329:
328:Classification
326:
317:
313:
309:
283:by animals or
125:
118:
103:
99:
95:
86:monosaccharide
65:
64:
50:
43:
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29:
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2713:
2710:
2708:
2705:
2703:
2700:
2698:
2695:
2693:
2690:
2688:
2687:Hemicellulose
2685:
2681:
2678:
2677:
2676:
2675:
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2667:
2665:
2664:
2660:
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2439:
2437:
2435:
2434:Disaccharides
2431:
2428:
2424:
2412:
2409:
2408:
2407:
2404:
2402:
2399:
2398:
2396:
2392:
2384:
2383:Sedoheptulose
2381:
2379:
2376:
2375:
2374:Ketoheptoses
2373:
2372:
2370:
2368:
2364:
2356:
2353:
2351:
2348:
2346:
2343:
2342:
2341:Deoxy sugars
2340:
2336:
2333:
2331:
2328:
2326:
2323:
2321:
2318:
2317:
2316:
2313:
2309:
2306:
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2257:
2249:
2246:
2245:
2244:
2241:
2237:
2234:
2232:
2229:
2228:
2227:Ketopentoses
2226:
2222:
2219:
2217:
2214:
2212:
2209:
2207:
2204:
2203:
2202:Aldopentoses
2201:
2200:
2198:
2196:
2192:
2184:
2181:
2180:
2178:
2174:
2171:
2169:
2166:
2165:
2164:Aldotetroses
2163:
2162:
2160:
2158:
2154:
2146:
2143:
2142:
2140:
2136:
2133:
2132:
2130:
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2127:
2125:
2121:
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2110:
2109:
2107:
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2042:
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2031:
2027:
2023:
2022:carbohydrates
2015:
2010:
2008:
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2001:
1996:
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1688:9780138924645
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1629:0-387-94951-8
1625:
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1599:
1597:3-527-31528-4
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1427:
1421:
1411:
1409:
1405:
1390:
1380:
1372:
1362:
1358:
1354:
1349:
1347:
1331:
1330:in solution.
1329:
1322:
1317:
1308:
1306:
1301:
1297:
1295:
1278:
1269:-glucose and
1247:
1229:
1211:
1193:
1184:
1182:
1181:chiral center
1177:
1175:
1171:
1166:
1164:
1160:
1156:
1153:
1149:
1144:
1142:
1134:
1125:
1123:
1113:
1111:
1107:
1103:
1101:
1095:
1093:
1089:
1085:
1081:
1077:
1073:
1069:
1068:unfermentable
1064:
1057:−C(=O)−(CHOH)
1047:3-Ketohexoses
1040:
1027:
1022:
1018:
1005:
1000:
996:
983:
978:
974:
961:
956:
955:
950:
937:
932:
928:
915:
910:
906:
893:
888:
884:
871:
866:
865:
864:
851:
838:
833:
829:
816:
811:
807:
794:
789:
785:
772:
767:
766:
765:
756:
753:
751:
747:
737:
722:
720:
716:
712:
708:
704:
700:
696:
692:
689:referring to
684:
680:
676:
672:
668:
664:
660:
657:
654:
653:
652:
650:
646:
641:
639:
635:
624:
622:
621:
567:
554:
549:
543:
530:
525:
519:
506:
501:
495:
482:
477:
471:
458:
453:
447:
434:
429:
423:
410:
405:
399:
386:
381:
380:
379:
377:
367:
363:
362:stereoisomers
359:
354:
352:
340:
325:
321:
305:
301:
297:
292:
290:
286:
282:
272:
268:
252:
248:
247:stereoisomers
243:
241:
239:
234:
230:
226:
222:
218:
210:
205:
203:
199:
195:
191:
187:
183:
179:
175:
171:
166:
164:
156:
153:), forming a
148:
140:
136:
129:
124:−C(=O)−(CHOH)
121:
112:
110:
91:
87:
83:
79:
69:
59:
47:
38:
26:
2668:
2657:
2639:
2571:Maltodextrin
2452:Isomaltulose
2259:
2243:Deoxy sugars
2179:Ketotetrose
2082:Mutarotation
1942:
1937:
1922:
1899:
1894:
1883:. Retrieved
1879:
1855:. Retrieved
1851:
1821:. Retrieved
1817:
1793:. Retrieved
1789:
1773:
1752:
1744:
1719:
1704:
1679:
1656:. Retrieved
1652:
1638:
1619:
1587:
1445:
1441:
1423:
1414:Deoxyhexoses
1381:
1350:
1337:
1320:
1318:
1314:
1305:mutarotation
1302:
1298:
1284:
1178:
1167:
1152:cyclic ether
1150:, after the
1145:
1133:ether bridge
1126:
1119:
1116:Cyclic forms
1099:
1096:
1091:
1087:
1079:
1066:In 1897, an
1065:
1050:
856:
757:
754:
743:
723:
718:
714:
710:
706:
702:
698:
694:
690:
688:
682:
678:
674:
670:
666:
662:
658:
655:
645:Emil Fischer
643:The chemist
642:
625:
618:
574:
355:
336:
319:
296:deoxyhexoses
295:
293:
244:
237:
236:
228:
216:
209:formyl group
206:
170:biochemistry
167:
134:
127:
119:
113:
107:, and their
81:
75:
2729:Xanthan gum
2717:Amylopectin
2589:Beta-glucan
2500:Maltotriose
2315:Ketohexoses
2268:Aldohexoses
2248:Deoxyribose
2183:Erythrulose
2141:Ketotriose
2131:Aldotriose
1984:Ketohexoses
1972:Aldohexoses
1462:-galactose)
1420:Deoxy sugar
1328:aldohexoses
1102:-3-hexulose
1084:portmanteau
740:Ketohexoses
366:enantiomers
333:Aldohexoses
281:metabolized
240:-ketohexose
147:single bond
2766:Categories
2505:Melezitose
2447:Isomaltose
2442:Cellobiose
2108:Aldodiose
1885:2018-04-26
1876:"Tagatose"
1857:2018-04-26
1842:"Sorbose,
1823:2018-04-26
1814:"Fructose"
1795:2018-04-26
1658:2018-04-26
1563:References
1521:-tagatose)
1490:sulfolipid
1482:-Quinovose
1418:See also:
1170:hemiacetal
593:-glucose,
298:, such as
229:ketohexose
217:aldohexose
190:glycosides
2659:Galactose
2614:Cellulose
2604:Sizofiran
2528:Stachyose
2510:Raffinose
2477:Trehalose
2462:Lactulose
2283:Galactose
2206:Arabinose
2168:Erythrose
2020:Types of
1874:Pubchem.
1840:Pubchem.
1812:Pubchem.
1786:-Psicose"
1778:Pubchem.
1757:. Wiley.
1649:-Psicose"
1643:Pubchem.
1517:(6-deoxy-
1515:-Fuculose
1504:(6-deoxy-
1502:-Pneumose
1484:(6-deoxy-
1475:-mannose)
1471:(6-deoxy-
1469:-Rhamnose
1458:(6-deoxy-
1426:hydroxyls
1379:-isomer.
1174:hemiketal
575:Of these
542:Galactose
285:fermented
186:cellulose
78:chemistry
2751:Category
2680:Glycogen
2663:Galactan
2641:Fructose
2626:Chitosan
2599:Lentinan
2548:Acarbose
2482:Turanose
2426:Multiple
2367:Heptoses
2355:Rhamnose
2350:Fuculose
2335:Tagatose
2320:Fructose
2236:Xylulose
2231:Ribulose
2195:Pentoses
2157:Tetroses
2060:Geometry
2051:Pyranose
2046:Furanose
1586:(2007).
1526:See also
1508:-talose)
1434:hydrogen
1404:Fructose
1361:tagatose
1357:fructose
1159:furanose
1148:pyranose
1092:fructose
1053:H−(CHOH)
1039:Tagatose
995:Fructose
949:Tagatose
905:Fructose
850:Tagatose
806:Fructose
750:fructose
717:actose,
649:mnemonic
339:aldehyde
304:rhamnose
194:dihexose
178:fructose
163:hydrogen
155:carbonyl
139:hydroxyl
133:, where
117:H−(CHOH)
58:Fructose
2772:Hexoses
2722:Amylose
2670:Glucose
2645:Fructan
2635:Dextran
2631:Dextrin
2609:Zymosan
2472:Sucrose
2467:Maltose
2457:Lactose
2406:Nonoses
2401:Octoses
2394:Above 7
2330:Sorbose
2325:Psicose
2303:Mannose
2288:Glucose
2278:Altrose
2260:Hexoses
2173:Threose
2124:Trioses
2029:General
1552:Heptose
1547:Pentose
1542:Tetrose
1456:-Fucose
1436:atoms (
1408:sucrose
1371:sorbose
1353:psicose
1346:glucose
1088:glucose
1080:glutose
1017:Sorbose
973:Psicose
927:Sorbose
883:Psicose
828:Sorbose
784:Psicose
705:nnose,
701:ucose,
470:Mannose
446:Glucose
422:Altrose
351:glucose
259:-" or "
198:sucrose
174:glucose
157:group (
37:Glucose
2712:Starch
2707:Pectin
2702:Mannan
2697:Lignin
2674:Glucan
2651:Inulin
2619:Chitin
2345:Fucose
2308:Talose
2293:Gulose
2273:Allose
2221:Xylose
2216:Ribose
2211:Lyxose
2101:Dioses
2077:Epimer
2067:Anomer
2041:Ketose
2036:Aldose
1761:
1737:
1686:
1626:
1594:
1557:Octose
1537:Triose
1495:(SQDG)
1141:oxygen
746:ketone
721:lose.
713:dose,
709:lose,
661:uists
566:Talose
494:Gulose
398:Allose
378:, are
300:fucose
289:yeasts
233:ketose
225:ketone
221:aldose
196:(like
188:, and
182:starch
90:carbon
82:hexose
2567:(IMO)
2561:(GOS)
2555:(FOS)
2537:Other
2298:Idose
1532:Diose
1072:bases
697:ose,
693:ose,
665:adly
518:Idose
213:−CH=O
84:is a
1759:ISBN
1684:ISBN
1624:ISBN
1592:ISBN
1359:and
1108:and
1100:xylo
1090:and
1082:, a
695:altr
685:nks.
681:lon
659:altr
638:bits
302:and
176:and
80:, a
1947:doi
1927:doi
1904:doi
1709:doi
1430:−OH
1137:−O−
1086:of
715:gal
691:all
679:gal
669:ke
656:All
569:111
545:110
521:101
497:100
473:011
449:010
425:001
401:000
287:by
159:C=O
143:−OH
76:In
2768::
2672:/
2661:/
2643:/
2633:/
1914:^
1878:.
1866:^
1850:.
1848:-"
1832:^
1816:.
1804:^
1788:.
1694:^
1667:^
1651:.
1606:^
1571:^
1438:−H
1355:,
1307:.
1251:β-
1233:α-
1215:β-
1197:α-
1129:=O
1112:.
1061:−H
752:.
719:ta
707:gu
703:ma
699:gl
683:ta
677:n
673:m
671:gu
667:ma
663:gl
623:.
353:.
347:−H
318:6−
314:12
291:.
204:.
184:,
151:=O
131:−H
126:6−
122:−1
100:12
2013:e
2006:t
1999:v
1949::
1929::
1906::
1888:.
1860:.
1845:D
1826:.
1798:.
1783:D
1780:"
1767:.
1730:L
1711::
1661:.
1647:D
1645:"
1632:.
1600:.
1519:L
1513:L
1506:L
1500:L
1486:D
1480:D
1473:L
1467:L
1460:L
1454:L
1446:x
1442:x
1428:(
1402:-
1399:D
1393:D
1384:D
1376:L
1366:D
1344:-
1341:D
1324:a
1321:K
1289:D
1279:.
1272:D
1266:D
1254:D
1236:D
1218:D
1200:D
1135:(
1059:3
1055:2
1037:-
1034:L
1015:-
1012:L
993:-
990:L
971:-
968:L
947:-
944:D
925:-
922:D
903:-
900:D
881:-
878:D
860:L
848:-
845:D
826:-
823:D
804:-
801:D
782:-
779:D
761:D
733:D
727:L
711:i
675:i
629:D
614:L
608:L
602:D
596:D
590:D
584:D
578:D
564:-
561:D
540:-
537:D
516:-
513:D
492:-
489:D
468:-
465:D
444:-
441:D
420:-
417:D
396:-
393:D
371:D
345:5
320:y
316:O
312:H
310:6
308:C
276:D
262:L
256:D
238:n
211:(
135:n
128:n
120:n
104:6
102:O
98:H
96:6
94:C
70:.
60:.
56:-
53:D
39:.
35:-
32:D
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