1204:
1222:
1168:
1186:
517:
1703:
825:
2715:
421:
397:
803:
759:
541:
469:
373:
25:
880:
493:
781:
46:
1014:
970:
1947:
1935:
445:
948:
902:
924:
992:
858:
1291:
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.
1275:
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.
1261:
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,
1159:, 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".
111:
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
1104:
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
1279:
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
628:, 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.
743:
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.
746:
In the linear form, the 2-ketohexoses have three chiral centers and therefore eight possible stereoisomers (2), comprising four pairs of enantiomers. The four
1093:
1082:
639:
device for remembering the order given above, which corresponds to the configurations about the chiral centers when ordered as 3-bit binary strings:
219:. However, the 3-ketohexoses have not been observed in nature, and are difficult to synthesize; so the term "ketohexose" usually means 2-ketohexose.
1089:
1148:
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
1144:
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
1909:
Akira Sera (1962): "Studies on the
Chemical Decomposition of Simple Sugars. XIII. Separation of the So-called Glutose (a 3-Ketohexose)".
1446:
1078:, and was claimed to be a 3-ketohexose. However, subsequent studies showed that the substance was a mixture of various other compounds.
1466:
1272:
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.
1866:
C. A. Lobry de Bruyn and W. Alberda van
Ekenstein (1897): "Action des alcalis sur les sucres. VI: La glutose et la pseudo‐fructose".
1979:
1730:
851:
forms have the hydroxyls on carbons 3, 4,and 5 reversed. Below are depiction of the eight isomers in an alternative style:
1701:-altrose", issued 1990-10-30, assigned to Government of the United States of America, Secretary of Agriculture
1655:
1595:
1563:
1364:
1747:
1612:
329:
The aldohexoses are a subclass of the hexoses which, in the linear form, have the carbonyl at carbon 1, forming an
1039:
In theory, the ketohexoses include also the 3-ketohexoses, which have the carbonyl in position 3; namely H–(CHOH)
316:
that can be described as derived from hexoses by replacement of one or more hydroxyl groups with hydrogen atoms.
246:
of the molecule, is to the right or to the left of the axis, respectively. These labels are independent of the
1460:
1951:
1939:
736:-containing hexose. The important ketohexoses are the 2-ketohexoses, and the most important 2-ketose is
1972:
1141:. The conventional numbering of the carbons in the closed form is the same as in the open-chain form.
1692:
230:. Each pair has a conventional name (like "glucose" or "fructose"), and the two members are labeled "
607:
2744:
2039:
1133:, that has the same ring. If the cycle has four carbon atoms (five in total), the form is called
2532:
1889:
George L. Clark, Hung Kao, Louis
Sattler, and F. W. Zerban (1949): "Chemical Nature of Glutose".
1105:
1047:–H. However, these compounds are not known to occur in nature, and are difficult to synthesize.
2718:
2526:
1965:
1809:
1843:
146:
atoms. The carbons are commonly numbered 1 to 6 starting at the end closest to the carbonyl.
2520:
1781:
516:
1416:
indicating the carbon with the affected hydroxyl. Some examples of biological interest are
1400:
The term "hexose" may sometimes be used to include the deoxyhexoses, which have one or more
226:
that differ in the spatial position of the hydroxyl groups. These species occur in pairs of
2659:
632:
250:
of the isomers. In general, only one of the two enantiomers occurs naturally (for example,
8:
420:
396:
1719:
1252:
1059:
824:
540:
468:
372:
363:
243:
67:
879:
1726:
1651:
1591:
1559:
1269:
1122:
If the cycle has five carbon atoms (six atoms in total), the closed form is called a
802:
758:
492:
2739:
2112:
1914:
1894:
1871:
1676:
1551:
1372:-Tagatose is a rare natural ketohexose that is found in small quantities in food.
1055:
247:
105:
2561:
2507:
2487:
2378:
1138:
1130:
182:
1203:
1013:
969:
780:
444:
200:. Otherwise, if the carbonyl position is 2 or 3, the sugar is a derivative of a
2548:
2345:
2102:
2079:
2059:
1401:
1302:
of 10.28, will only deprotonate at high pH, so are marginally less stable than
1221:
1167:
227:
85:
1382:
is responsible for the sweet taste of many fruits, and is a building block of
1185:
947:
923:
901:
2733:
2654:
2571:
2459:
2350:
1875:
621:
345:
991:
857:
142:
group (C=O). The remaining bonds of the carbon atoms are satisfied by seven
2538:
2419:
2401:
2049:
1989:
1280:
1156:
1051:
349:
261:
223:
189:
174:
150:
1111:
The reaction turns the =O group into a hydroxyl, and the hydroxyl into an
2696:
2684:
2556:
2467:
2215:
2210:
2150:
1957:
1918:
1395:
1112:
1067:
135:
1898:
1680:
2472:
2414:
2409:
2282:
2235:
1457:
1303:
1145:
624:
from 0 to 7, namely 000, 001, 010, 011, 100, 101, 110, 111. The three
353:
257:
724:-isomers; with all hydroxyls reversed, including the one on carbon 5.
222:
In the linear form, there are 16 aldohexoses and eight 2-ketohexoses,
2630:
2626:
2581:
2495:
2477:
2444:
2429:
2250:
2173:
2135:
1149:
529:
170:
166:
77:
1324:, which is the main "fuel" for metabolism in many living organisms.
2647:
2608:
2593:
2566:
2515:
2449:
2322:
2317:
2302:
2287:
2203:
2198:
2018:
2013:
1479:
1433:
1405:
1379:
1336:
1332:
1295:
2-Ketohexoses are stable over a wide pH range, and with a primary p
1134:
1123:
1026:
982:
936:
892:
837:
793:
737:
636:
330:
280:
158:
143:
139:
131:
57:
24:
1115:(–O–) between the two carbon atoms, thus creating a ring with one
2689:
2669:
2637:
2612:
2602:
2598:
2576:
2439:
2434:
2424:
2334:
2297:
2292:
2270:
2255:
2245:
2162:
2140:
2124:
1519:
1514:
1509:
1383:
1346:
1328:
1321:
1004:
960:
914:
870:
815:
771:
457:
433:
409:
338:
178:
154:
36:
1088:, through a rather complex route, was first reported in 1961 by
2679:
2674:
2664:
2641:
2618:
2586:
2373:
2368:
2312:
2275:
2260:
2240:
2188:
2183:
2178:
2091:
2044:
2034:
2008:
2003:
1946:
1934:
1524:
1504:
1420:
1408:
atoms (–H). It is named as the parent hexose, with the prefix "
1116:
733:
575:-altrose occur in living organisms, but only three are common:
553:
481:
385:
276:
209:
201:
197:
162:
89:
2265:
2068:
1499:
1127:
505:
265:
45:
1868:
Recueil des
Travaux Chimiques des Pays-Bas et de la Belgique
599:-isomers are generally absent in living organisms; however,
242:-", depending on whether the hydroxyl in position 5, in the
1108:
between the carbonyl group and one of the hydroxyl groups.
1081:
The unequivocal synthesis and isolation of a 3-ketohexose,
1646:
Robert
Thornton Morrison and Robert Neilson Boyd (1998):
1363:-Sorbose is commonly used in the commercial synthesis of
1314:
The aldohexose that is most important in biochemistry is
625:
614:
When drawn in this order, the
Fischer projections of the
605:-altrose has been isolated from strains of the bacterium
718:-aldohexoses are the mirror images of the corresponding
130:
is 1, 2, 3, 4, 5. Namely, five of the carbons have one
1695:, Stack; Robert J., "Microbial production of
1556:
161:) and as building blocks of other compounds such as
1550:
1718:
271:The term "hexose" sometimes is assumed to include
1671:George U. Yuen and James M. Sugihara (1961): "".
92:atoms. The chemical formula for all hexoses is C
2731:
1691:
620:-aldohexoses can be identified with the 3-digit
1837:
1835:
1054:product obtained by treatment of fructose with
188:When the carbonyl is in position 1, forming an
1803:
1801:
1775:
1773:
1309:
1973:
1716:
1585:
1155:The closure turns the carboxyl carbon into a
134:functional group (–OH) each, connected by a
1885:
1883:
1832:
1739:
181:) by a condensation reaction that makes 1,6-
1798:
1770:
1581:
1579:
1577:
1575:
138:, and one has an oxo group (=O), forming a
1987:
1980:
1966:
1667:
1665:
1663:
1642:
1640:
1638:
1636:
1546:
1544:
1542:
1540:
1911:Bulletin of the Chemical Society of Japan
1880:
1860:
1913:, volume 35, issue 12, pages 2031-2033.
1903:
1572:
333:derivative with structure H–C(=O)–(CHOH)
1710:
1675:, volume 26, issue 5, pages 1598-1601.
1660:
1633:
1537:
344:In linear form, an aldohexose has four
153:, both as isolated molecules (such as
2732:
1891:Industrial & Engineering Chemistry
1286:
635:is said to have devised the following
1961:
1893:, volume 41, issue 3, pages 530-533.
1870:, volume 16, issue 9, pages 274-281.
1268:-glucose forms an α crystal that has
1588:Essentials of Carbohydrate Chemistry
348:, which give 16 possible aldohexose
1841:
1807:
1779:
1745:
1721:The vocabulary of organic chemistry
1610:
337:–H. The most important example is
149:Hexoses are extremely important in
13:
712:The Fischer diagrams of the eight
14:
2756:
1927:
1604:
356:. The linear forms of the eight
319:
283:: compounds with general formula
2714:
2713:
1945:
1933:
1456:-glucose), found as part of the
1220:
1202:
1184:
1166:
1034:
1012:
990:
968:
946:
922:
900:
878:
856:
823:
801:
779:
757:
539:
515:
491:
467:
443:
419:
395:
371:
192:(–CH=O), the sugar is called an
44:
23:
1389:
1119:atom and four or five carbons.
1099:
1685:
1461:sulfoquinovosyl diacylglycerol
727:
324:
66:Two important hexoses, in the
1:
1530:
1019:
997:
975:
953:
929:
907:
885:
863:
830:
808:
786:
764:
546:
522:
498:
474:
450:
426:
402:
378:
1673:Journal of Organic Chemistry
7:
1717:Milton Orchin, ed. (1980).
1493:
1310:Natural occurrence and uses
1152:with a five-membered ring.
10:
2761:
1393:
352:(2),comprising 8 pairs of
2709:
2547:
2504:
2486:
2458:
2400:
2393:
2361:
2333:
2226:
2161:
2123:
2090:
2067:
2058:
2027:
1996:
1558:(1 ed.). Wiley-VCH.
608:Butyrivibrio fibrisolvens
2040:Cyclohexane conformation
1876:10.1002/recl.18970160903
1848:pubchem.ncbi.nlm.nih.gov
1820:pubchem.ncbi.nlm.nih.gov
1786:pubchem.ncbi.nlm.nih.gov
1758:pubchem.ncbi.nlm.nih.gov
1621:pubchem.ncbi.nlm.nih.gov
1590:(1 ed.). Springer.
1349:occurs naturally as the
88:(simple sugar) with six
2533:Isomaltooligosaccharide
1339:occur naturally as the
2527:Galactooligosaccharide
1586:John F. Robyt (1997).
1106:internal rearrangement
2521:Fructooligosaccharide
1693:US patent 4966845
1062:, was given the name
569:-isomers, all except
362:-aldohexoses, in the
256:-glucose) and can be
16:6-Carbon simple sugar
1954:at Wikimedia Commons
1942:at Wikimedia Commons
1919:10.1246/bcsj.35.2031
1386:, the common sugar.
208:, a special case of
196:, a special case of
173:. Hexoses can form
1899:10.1021/ie50471a020
1681:10.1021/jo01064a070
1552:Thisbe K. Lindhorst
1287:Chemical properties
1137:after the compound
212:; specifically, an
1404:(–OH) replaced by
1345:-isomers, whereas
1327:The 2-ketohexoses
1253:Haworth projection
1251:-fructose, in the
1060:lead(II) hydroxide
845:The corresponding
732:A ketohexose is a
364:Fischer projection
244:Fischer projection
204:, and is called a
108:is 180.156 g/mol.
68:Fischer projection
2727:
2726:
2705:
2704:
2389:
2388:
1950:Media related to
1938:Media related to
1732:978-0-471-04491-8
1648:Organic Chemistry
1616:
1270:specific rotation
1094:James M. Sugihara
2752:
2717:
2716:
2508:oligosaccharides
2488:Tetrasaccharides
2398:
2397:
2113:Dihydroxyacetone
2065:
2064:
1982:
1975:
1968:
1959:
1958:
1949:
1937:
1921:
1907:
1901:
1887:
1878:
1864:
1858:
1857:
1855:
1854:
1839:
1830:
1829:
1827:
1826:
1815:
1814:
1805:
1796:
1795:
1793:
1792:
1777:
1768:
1767:
1765:
1764:
1753:
1752:
1743:
1737:
1736:
1724:
1714:
1708:
1707:
1706:
1702:
1700:
1699:
1689:
1683:
1669:
1658:
1644:
1631:
1630:
1628:
1627:
1614:
1608:
1602:
1601:
1583:
1570:
1569:
1548:
1488:
1482:
1475:
1469:
1455:
1449:
1442:
1436:
1429:
1423:
1377:
1376:
1371:
1370:
1362:
1361:
1354:
1353:
1344:
1343:
1319:
1318:
1267:
1266:
1250:
1249:
1244:
1243:
1239:Closed forms of
1233:-Fructofuranose.
1232:
1231:
1224:
1215:-Fructofuranose.
1214:
1213:
1206:
1196:
1195:
1188:
1178:
1177:
1170:
1058:, in particular
1024:
1023:
1016:
1002:
1001:
994:
980:
979:
972:
958:
957:
950:
934:
933:
926:
912:
911:
904:
890:
889:
882:
868:
867:
860:
850:
849:
835:
834:
827:
813:
812:
805:
791:
790:
783:
769:
768:
761:
751:
750:
723:
722:
717:
716:
619:
618:
604:
603:
598:
597:
592:
591:
587:-galactose, and
586:
585:
580:
579:
574:
573:
568:
567:
551:
550:
543:
527:
526:
519:
503:
502:
495:
479:
478:
471:
455:
454:
447:
431:
430:
423:
407:
406:
399:
383:
382:
375:
361:
360:
315:
314:
313:
302:
301:
293:
292:
255:
254:
248:optical activity
241:
240:
235:
234:
106:molecular weight
55:
54:
48:
34:
33:
27:
2760:
2759:
2755:
2754:
2753:
2751:
2750:
2749:
2745:Monosaccharides
2730:
2729:
2728:
2723:
2701:
2562:Oat beta-glucan
2549:Polysaccharides
2543:
2506:
2500:
2482:
2454:
2385:
2379:Neuraminic acid
2357:
2329:
2222:
2157:
2119:
2086:
2060:Monosaccharides
2054:
2023:
1992:
1986:
1930:
1925:
1924:
1908:
1904:
1888:
1881:
1865:
1861:
1852:
1850:
1840:
1833:
1824:
1822:
1812:
1811:
1806:
1799:
1790:
1788:
1778:
1771:
1762:
1760:
1750:
1749:
1744:
1740:
1733:
1715:
1711:
1704:
1697:
1696:
1690:
1686:
1670:
1661:
1650:, 6th edition.
1645:
1634:
1625:
1623:
1609:
1605:
1598:
1584:
1573:
1566:
1549:
1538:
1533:
1496:
1486:
1480:
1473:
1467:
1453:
1447:
1440:
1434:
1427:
1421:
1398:
1392:
1374:
1373:
1368:
1367:
1359:
1358:
1351:
1350:
1341:
1340:
1316:
1315:
1312:
1301:
1289:
1264:
1263:
1259:
1258:
1257:
1256:
1247:
1246:
1241:
1240:
1236:
1235:
1234:
1229:
1228:
1225:
1217:
1216:
1211:
1210:
1207:
1199:
1198:
1197:-Glucopyranose.
1193:
1192:
1189:
1181:
1180:
1179:-Glucopyranose.
1175:
1174:
1171:
1139:tetrahydrofuran
1131:tetrahydropyran
1102:
1046:
1042:
1037:
1030:
1029:
1021:
1020:
1017:
1008:
1007:
999:
998:
995:
986:
985:
977:
976:
973:
964:
963:
955:
954:
951:
940:
939:
931:
930:
927:
918:
917:
909:
908:
905:
896:
895:
887:
886:
883:
874:
873:
865:
864:
861:
847:
846:
841:
840:
832:
831:
828:
819:
818:
810:
809:
806:
797:
796:
788:
787:
784:
775:
774:
766:
765:
762:
748:
747:
730:
720:
719:
714:
713:
616:
615:
601:
600:
595:
594:
589:
588:
583:
582:
577:
576:
571:
570:
565:
564:
559:
558:
556:
548:
547:
544:
535:
534:
532:
524:
523:
520:
511:
510:
508:
500:
499:
496:
487:
486:
484:
476:
475:
472:
463:
462:
460:
452:
451:
448:
439:
438:
436:
428:
427:
424:
415:
414:
412:
404:
403:
400:
391:
390:
388:
380:
379:
376:
358:
357:
336:
327:
322:
312:
306:
305:
304:
300:
297:
296:
295:
291:
288:
287:
286:
284:
252:
251:
238:
237:
232:
231:
228:optical isomers
183:glycosidic bond
125:
118:
103:
99:
95:
74:
73:
72:
71:
63:
62:
61:
52:
51:
49:
41:
40:
31:
30:
28:
17:
12:
11:
5:
2758:
2748:
2747:
2742:
2725:
2724:
2722:
2721:
2710:
2707:
2706:
2703:
2702:
2700:
2699:
2694:
2693:
2692:
2687:
2677:
2672:
2667:
2662:
2660:Levan beta 2→6
2657:
2652:
2651:
2650:
2634:
2623:
2622:
2621:
2605:
2596:
2591:
2590:
2589:
2584:
2579:
2574:
2569:
2564:
2553:
2551:
2545:
2544:
2542:
2541:
2536:
2530:
2524:
2518:
2512:
2510:
2502:
2501:
2499:
2498:
2492:
2490:
2484:
2483:
2481:
2480:
2475:
2470:
2464:
2462:
2460:Trisaccharides
2456:
2455:
2453:
2452:
2447:
2442:
2437:
2432:
2427:
2422:
2417:
2412:
2406:
2404:
2395:
2391:
2390:
2387:
2386:
2384:
2383:
2382:
2381:
2371:
2365:
2363:
2359:
2358:
2356:
2355:
2354:
2353:
2348:
2346:Mannoheptulose
2339:
2337:
2331:
2330:
2328:
2327:
2326:
2325:
2320:
2315:
2307:
2306:
2305:
2300:
2295:
2290:
2280:
2279:
2278:
2273:
2268:
2263:
2258:
2253:
2248:
2243:
2232:
2230:
2224:
2223:
2221:
2220:
2219:
2218:
2208:
2207:
2206:
2201:
2193:
2192:
2191:
2186:
2181:
2176:
2167:
2165:
2159:
2158:
2156:
2155:
2154:
2153:
2145:
2144:
2143:
2138:
2129:
2127:
2121:
2120:
2118:
2117:
2116:
2115:
2107:
2106:
2105:
2103:Glyceraldehyde
2096:
2094:
2088:
2087:
2085:
2084:
2083:
2082:
2080:Glycolaldehyde
2073:
2071:
2062:
2056:
2055:
2053:
2052:
2047:
2042:
2037:
2031:
2029:
2025:
2024:
2022:
2021:
2016:
2011:
2006:
2000:
1998:
1994:
1993:
1985:
1984:
1977:
1970:
1962:
1956:
1955:
1943:
1929:
1928:External links
1926:
1923:
1922:
1902:
1879:
1859:
1831:
1797:
1769:
1738:
1731:
1709:
1684:
1659:
1632:
1603:
1596:
1571:
1564:
1535:
1534:
1532:
1529:
1528:
1527:
1522:
1517:
1512:
1507:
1502:
1495:
1492:
1491:
1490:
1477:
1464:
1444:
1431:
1412:-deoxy-", the
1391:
1388:
1365:ascorbic acid.
1311:
1308:
1299:
1288:
1285:
1238:
1237:
1226:
1219:
1218:
1208:
1201:
1200:
1190:
1183:
1182:
1172:
1165:
1164:
1163:
1162:
1161:
1101:
1098:
1090:George U. Yuen
1044:
1040:
1036:
1033:
1032:
1031:
1018:
1011:
1009:
996:
989:
987:
974:
967:
965:
952:
945:
942:
941:
928:
921:
919:
906:
899:
897:
884:
877:
875:
862:
855:
843:
842:
829:
822:
820:
807:
800:
798:
785:
778:
776:
763:
756:
752:-isomers are:
729:
726:
675:
674:
622:binary numbers
593:-mannose. The
561:
560:
545:
538:
536:
521:
514:
512:
497:
490:
488:
473:
466:
464:
449:
442:
440:
425:
418:
416:
401:
394:
392:
377:
370:
346:chiral centres
334:
326:
323:
321:
320:Classification
318:
307:
298:
289:
260:by animals or
120:
113:
101:
97:
93:
86:monosaccharide
65:
64:
50:
43:
42:
29:
22:
21:
20:
19:
18:
15:
9:
6:
4:
3:
2:
2757:
2746:
2743:
2741:
2738:
2737:
2735:
2720:
2712:
2711:
2708:
2698:
2695:
2691:
2688:
2686:
2683:
2682:
2681:
2678:
2676:
2673:
2671:
2668:
2666:
2663:
2661:
2658:
2656:
2655:Hemicellulose
2653:
2649:
2646:
2645:
2644:
2643:
2639:
2635:
2633:
2632:
2628:
2624:
2620:
2617:
2616:
2615:
2614:
2610:
2606:
2604:
2600:
2597:
2595:
2592:
2588:
2585:
2583:
2580:
2578:
2575:
2573:
2570:
2568:
2565:
2563:
2560:
2559:
2558:
2555:
2554:
2552:
2550:
2546:
2540:
2537:
2534:
2531:
2528:
2525:
2522:
2519:
2517:
2514:
2513:
2511:
2509:
2503:
2497:
2494:
2493:
2491:
2489:
2485:
2479:
2476:
2474:
2471:
2469:
2466:
2465:
2463:
2461:
2457:
2451:
2448:
2446:
2443:
2441:
2438:
2436:
2433:
2431:
2428:
2426:
2423:
2421:
2418:
2416:
2413:
2411:
2408:
2407:
2405:
2403:
2402:Disaccharides
2399:
2396:
2392:
2380:
2377:
2376:
2375:
2372:
2370:
2367:
2366:
2364:
2360:
2352:
2351:Sedoheptulose
2349:
2347:
2344:
2343:
2342:Ketoheptoses
2341:
2340:
2338:
2336:
2332:
2324:
2321:
2319:
2316:
2314:
2311:
2310:
2309:Deoxy sugars
2308:
2304:
2301:
2299:
2296:
2294:
2291:
2289:
2286:
2285:
2284:
2281:
2277:
2274:
2272:
2269:
2267:
2264:
2262:
2259:
2257:
2254:
2252:
2249:
2247:
2244:
2242:
2239:
2238:
2237:
2234:
2233:
2231:
2229:
2225:
2217:
2214:
2213:
2212:
2209:
2205:
2202:
2200:
2197:
2196:
2195:Ketopentoses
2194:
2190:
2187:
2185:
2182:
2180:
2177:
2175:
2172:
2171:
2170:Aldopentoses
2169:
2168:
2166:
2164:
2160:
2152:
2149:
2148:
2146:
2142:
2139:
2137:
2134:
2133:
2132:Aldotetroses
2131:
2130:
2128:
2126:
2122:
2114:
2111:
2110:
2108:
2104:
2101:
2100:
2098:
2097:
2095:
2093:
2089:
2081:
2078:
2077:
2075:
2074:
2072:
2070:
2066:
2063:
2061:
2057:
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2043:
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2038:
2036:
2033:
2032:
2030:
2026:
2020:
2017:
2015:
2012:
2010:
2007:
2005:
2002:
2001:
1999:
1995:
1991:
1990:carbohydrates
1983:
1978:
1976:
1971:
1969:
1964:
1963:
1960:
1953:
1948:
1944:
1941:
1936:
1932:
1931:
1920:
1916:
1912:
1906:
1900:
1896:
1892:
1886:
1884:
1877:
1873:
1869:
1863:
1849:
1845:
1838:
1836:
1821:
1817:
1804:
1802:
1787:
1783:
1776:
1774:
1759:
1755:
1742:
1734:
1728:
1723:
1722:
1713:
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1657:
1656:9780138924645
1653:
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1637:
1622:
1618:
1607:
1599:
1597:0-387-94951-8
1593:
1589:
1582:
1580:
1578:
1576:
1567:
1565:3-527-31528-4
1561:
1557:
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1536:
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1523:
1521:
1518:
1516:
1513:
1511:
1508:
1506:
1503:
1501:
1498:
1497:
1484:
1478:
1471:
1465:
1462:
1459:
1451:
1445:
1438:
1432:
1425:
1419:
1418:
1417:
1415:
1411:
1407:
1403:
1397:
1387:
1385:
1381:
1366:
1356:
1348:
1338:
1334:
1330:
1325:
1323:
1307:
1306:in solution.
1305:
1298:
1293:
1284:
1282:
1277:
1273:
1271:
1254:
1245:-glucose and
1223:
1205:
1187:
1169:
1160:
1158:
1157:chiral center
1153:
1151:
1147:
1142:
1140:
1136:
1132:
1129:
1125:
1120:
1118:
1114:
1109:
1107:
1097:
1095:
1091:
1087:
1085:
1079:
1077:
1073:
1069:
1065:
1061:
1057:
1053:
1052:unfermentable
1048:
1043:–C(=O)–(CHOH)
1035:3-Ketohexoses
1028:
1015:
1010:
1006:
993:
988:
984:
971:
966:
962:
949:
944:
943:
938:
925:
920:
916:
903:
898:
894:
881:
876:
872:
859:
854:
853:
852:
839:
826:
821:
817:
804:
799:
795:
782:
777:
773:
760:
755:
754:
753:
744:
741:
739:
735:
725:
710:
708:
704:
700:
696:
692:
688:
684:
680:
677:referring to
672:
668:
664:
660:
656:
652:
648:
645:
642:
641:
640:
638:
634:
629:
627:
623:
612:
610:
609:
555:
542:
537:
531:
518:
513:
507:
494:
489:
483:
470:
465:
459:
446:
441:
435:
422:
417:
411:
398:
393:
387:
374:
369:
368:
367:
365:
355:
351:
350:stereoisomers
347:
342:
340:
332:
317:
311:
282:
278:
274:
269:
267:
263:
259:
249:
245:
229:
225:
224:stereoisomers
220:
218:
216:
211:
207:
203:
199:
195:
191:
186:
184:
180:
176:
172:
168:
164:
160:
156:
152:
147:
145:
141:
137:
133:
129:
124:
119:–C(=O)–(CHOH)
116:
109:
107:
91:
87:
83:
79:
69:
59:
47:
38:
26:
2636:
2625:
2607:
2539:Maltodextrin
2420:Isomaltulose
2227:
2211:Deoxy sugars
2147:Ketotetrose
2050:Mutarotation
1910:
1905:
1890:
1867:
1862:
1851:. Retrieved
1847:
1823:. Retrieved
1819:
1789:. Retrieved
1785:
1761:. Retrieved
1757:
1741:
1720:
1712:
1687:
1672:
1647:
1624:. Retrieved
1620:
1606:
1587:
1555:
1413:
1409:
1399:
1390:Deoxyhexoses
1357:
1326:
1313:
1296:
1294:
1290:
1281:mutarotation
1278:
1274:
1260:
1154:
1143:
1128:cyclic ether
1126:, after the
1121:
1113:ether bridge
1110:
1103:
1100:Cyclic forms
1083:
1080:
1075:
1071:
1063:
1050:In 1897, an
1049:
1038:
844:
745:
742:
731:
711:
706:
702:
698:
694:
690:
686:
682:
678:
676:
670:
666:
662:
658:
654:
650:
646:
643:
633:Emil Fischer
631:The chemist
630:
613:
606:
562:
343:
328:
309:
273:deoxyhexoses
272:
270:
221:
214:
213:
205:
193:
190:formyl group
187:
151:biochemistry
148:
127:
122:
114:
110:
104:, and their
81:
75:
2697:Xanthan gum
2685:Amylopectin
2557:Beta-glucan
2468:Maltotriose
2283:Ketohexoses
2236:Aldohexoses
2216:Deoxyribose
2151:Erythrulose
2109:Ketotriose
2099:Aldotriose
1952:Ketohexoses
1940:Aldohexoses
1430:-galactose)
1396:Deoxy sugar
1304:aldohexoses
1086:-3-hexulose
1068:portmanteau
728:Ketohexoses
354:enantiomers
325:Aldohexoses
258:metabolized
217:-ketohexose
136:single bond
2734:Categories
2473:Melezitose
2415:Isomaltose
2410:Cellobiose
2076:Aldodiose
1853:2018-04-26
1844:"Tagatose"
1825:2018-04-26
1810:"Sorbose,
1791:2018-04-26
1782:"Fructose"
1763:2018-04-26
1626:2018-04-26
1531:References
1489:-tagatose)
1458:sulfolipid
1450:-Quinovose
1394:See also:
1146:hemiacetal
581:-glucose,
275:, such as
206:ketohexose
194:aldohexose
171:glycosides
126:–H, where
2627:Galactose
2582:Cellulose
2572:Sizofiran
2496:Stachyose
2478:Raffinose
2445:Trehalose
2430:Lactulose
2251:Galactose
2174:Arabinose
2136:Erythrose
1988:Types of
1842:Pubchem.
1808:Pubchem.
1780:Pubchem.
1754:-Psicose"
1746:Pubchem.
1725:. Wiley.
1617:-Psicose"
1611:Pubchem.
1485:(6-deoxy-
1483:-Fuculose
1472:(6-deoxy-
1470:-Pneumose
1452:(6-deoxy-
1443:-mannose)
1439:(6-deoxy-
1437:-Rhamnose
1426:(6-deoxy-
1402:hydroxyls
1355:-isomer.
1150:hemiketal
563:Of these
530:Galactose
262:fermented
167:cellulose
78:chemistry
2719:Category
2648:Glycogen
2631:Galactan
2609:Fructose
2594:Chitosan
2567:Lentinan
2516:Acarbose
2450:Turanose
2394:Multiple
2335:Heptoses
2323:Rhamnose
2318:Fuculose
2303:Tagatose
2288:Fructose
2204:Xylulose
2199:Ribulose
2163:Pentoses
2125:Tetroses
2028:Geometry
2019:Pyranose
2014:Furanose
1554:(2007).
1494:See also
1476:-talose)
1406:hydrogen
1380:Fructose
1337:tagatose
1333:fructose
1135:furanose
1124:pyranose
1076:fructose
1027:Tagatose
983:Fructose
937:Tagatose
893:Fructose
838:Tagatose
794:Fructose
738:fructose
705:actose,
637:mnemonic
331:aldehyde
281:rhamnose
175:dihexose
159:fructose
144:hydrogen
140:carbonyl
132:hydroxyl
112:H–(CHOH)
58:Fructose
2740:Hexoses
2690:Amylose
2638:Glucose
2613:Fructan
2603:Dextran
2599:Dextrin
2577:Zymosan
2440:Sucrose
2435:Maltose
2425:Lactose
2374:Nonoses
2369:Octoses
2362:Above 7
2298:Sorbose
2293:Psicose
2271:Mannose
2256:Glucose
2246:Altrose
2228:Hexoses
2141:Threose
2092:Trioses
1997:General
1520:Heptose
1515:Pentose
1510:Tetrose
1424:-Fucose
1384:sucrose
1347:sorbose
1329:psicose
1322:glucose
1072:glucose
1064:glutose
1005:Sorbose
961:Psicose
915:Sorbose
871:Psicose
816:Sorbose
772:Psicose
693:nnose,
689:ucose,
458:Mannose
434:Glucose
410:Altrose
339:glucose
236:-" or "
179:sucrose
155:glucose
37:Glucose
2680:Starch
2675:Pectin
2670:Mannan
2665:Lignin
2642:Glucan
2619:Inulin
2587:Chitin
2313:Fucose
2276:Talose
2261:Gulose
2241:Allose
2189:Xylose
2184:Ribose
2179:Lyxose
2069:Dioses
2045:Epimer
2035:Anomer
2009:Ketose
2004:Aldose
1729:
1705:
1654:
1594:
1562:
1525:Octose
1505:Triose
1463:(SQDG)
1117:oxygen
734:ketone
709:lose.
701:dose,
697:lose,
649:uists
554:Talose
482:Gulose
386:Allose
366:, are
277:fucose
266:yeasts
210:ketose
202:ketone
198:aldose
177:(like
169:, and
163:starch
90:carbon
82:hexose
2535:(IMO)
2529:(GOS)
2523:(FOS)
2505:Other
2266:Idose
1500:Diose
1056:bases
685:ose,
681:ose,
653:adly
506:Idose
84:is a
1727:ISBN
1652:ISBN
1592:ISBN
1560:ISBN
1335:and
1092:and
1084:xylo
1074:and
1066:, a
683:altr
673:nks.
669:lon
647:altr
626:bits
279:and
157:and
80:, a
1915:doi
1895:doi
1872:doi
1677:doi
1070:of
703:gal
679:all
667:gal
657:ke
644:All
557:111
533:110
509:101
485:100
461:011
437:010
413:001
389:000
264:by
76:In
2736::
2640:/
2629:/
2611:/
2601:/
1882:^
1846:.
1834:^
1818:.
1816:-"
1800:^
1784:.
1772:^
1756:.
1662:^
1635:^
1619:.
1574:^
1539:^
1331:,
1283:.
1227:β-
1209:α-
1191:β-
1173:α-
1096:.
740:.
707:ta
695:gu
691:ma
687:gl
671:ta
665:n
661:m
659:gu
655:ma
651:gl
611:.
341:.
308:6-
299:12
268:.
185:.
165:,
121:6−
117:−1
98:12
1981:e
1974:t
1967:v
1917::
1897::
1874::
1856:.
1828:.
1813:D
1794:.
1766:.
1751:D
1748:"
1735:.
1698:L
1679::
1629:.
1615:D
1613:"
1600:.
1568:.
1487:L
1481:L
1474:L
1468:L
1454:D
1448:D
1441:L
1435:L
1428:L
1422:L
1414:x
1410:x
1378:-
1375:D
1369:D
1360:D
1352:L
1342:D
1320:-
1317:D
1300:a
1297:K
1265:D
1255:.
1248:D
1242:D
1230:D
1212:D
1194:D
1176:D
1045:3
1041:2
1025:-
1022:L
1003:-
1000:L
981:-
978:L
959:-
956:L
935:-
932:D
913:-
910:D
891:-
888:D
869:-
866:D
848:L
836:-
833:D
814:-
811:D
792:-
789:D
770:-
767:D
749:D
721:D
715:L
699:i
663:i
617:D
602:L
596:L
590:D
584:D
578:D
572:D
566:D
552:-
549:D
528:-
525:D
504:-
501:D
480:-
477:D
456:-
453:D
432:-
429:D
408:-
405:D
384:-
381:D
359:D
335:5
310:y
303:O
294:H
290:6
285:C
253:D
239:L
233:D
215:n
128:n
123:n
115:n
102:6
100:O
96:H
94:6
70:.
60:.
56:-
53:D
39:.
35:-
32:D
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
