1659:
643:
661:
371:
323:
545:
527:
389:
561:
511:
437:
421:
355:
339:
405:
141:
Like some other monosaccharides, pentoses exist in two forms, open-chain (linear) or closed-chain (cyclic), that easily convert into each other in water solutions. The linear form of a pentose, which usually exists only in solutions, has an open-chain backbone of five carbons. Four of these
621:, which may have any of two configurations, depending on the position of the new hydroxyl. Therefore, each linear form can produce two distinct closed forms, identified by prefixes "α" and "β".
503:
The 2-ketopentoses have two chiral centers; therefore, four (2) different stereoisomers are possible. The 3-ketopentoses are rare.
923:
603:
molecule, with a ring consisting of one oxygen atom and usually four carbon atoms; the cyclic compounds are then called
862:
222:
that can be described as derived from pentoses by replacement of one or more hydroxyl groups with hydrogen atoms.
889:
710:
The most important tests for pentoses rely on converting the pentose to furfural, which then reacts with a
916:
17:
470:
115:
234:
are a subclass of the pentoses which, in the linear form, have the carbonyl at carbon 1, forming an
983:
266:–H (3-ketopentose). The latter is not known to occur in nature and are difficult to synthesize.
1476:
596:
1662:
1470:
909:
813:
879:
852:
1464:
482:
131:
1603:
735:
273:
that differ in the spatial position of the hydroxyl groups. These forms occur in pairs of
8:
719:
486:
474:
119:
746:. In each of these tests, pentoses react much more strongly and quickly than hexoses.
1683:
885:
858:
833:
775:
762:
1056:
825:
715:
290:
146:
84:
50:
1505:
1451:
1431:
1322:
611:
600:
111:
1492:
1289:
1046:
1023:
1003:
739:
731:
723:
584:
274:
39:
1677:
1598:
1515:
1403:
1294:
837:
829:
670:
308:
150:
1482:
1363:
1345:
993:
933:
618:
312:
270:
127:
91:
157:
group (C=O). The remaining bonds of the carbon atoms are satisfied by six
1640:
1628:
1500:
1411:
1159:
1154:
1094:
901:
851:
Seager, Spencer L.; Slabaugh, Michael R.; Hansen, Maren S. (2016-12-05).
795:
711:
652:
630:
592:
462:
247:
231:
186:
135:
103:
591:
in another carbon, turning the carbonyl into a hydroxyl and creating an
269:
In the open form, there are eight aldopentoses and four 2-ketopentoses,
153:, and one has an oxygen atom connected by a double bond (=O), forming a
1416:
1358:
1353:
1226:
1179:
478:
123:
660:
642:
1574:
1570:
1525:
1439:
1421:
1388:
1373:
1194:
1117:
1079:
881:
Introduction to
Organic Laboratory Techniques: A Small Scale Approach
684:
398:
332:
31:
1591:
1552:
1537:
1510:
1459:
1393:
1266:
1261:
1246:
1231:
1147:
1142:
962:
957:
727:
699:
604:
588:
570:
554:
536:
520:
235:
158:
154:
143:
1633:
1613:
1581:
1556:
1546:
1542:
1520:
1383:
1378:
1368:
1278:
1241:
1236:
1214:
1199:
1189:
1084:
1068:
743:
695:
370:
1623:
1618:
1608:
1585:
1562:
1530:
1317:
1312:
1256:
1219:
1204:
1184:
1171:
1132:
1127:
1122:
1035:
988:
978:
952:
947:
688:
498:
454:
446:
430:
414:
380:
364:
348:
302:
251:
243:
95:
43:
322:
1209:
1012:
608:
544:
526:
388:
583:
The closed or cyclic form of a pentose is created when the
560:
510:
436:
420:
354:
338:
46:
466:
458:
404:
250:
instead have the carbonyl at positions 2 or 3, forming a
161:
atoms. Thus the structure of the linear form is H–(CHOH)
107:
99:
469:. Phosphorylated pentoses are important products of the
783:". PubChem compound webpage, accessed on 2010-02-06.
850:
181:The term "pentose" sometimes is assumed to include
635:The one deoxypentose has two total stereoisomers.
134:(E4P), which is used in the synthesis of aromatic
796:Morrison, Robert Thornton; Boyd, Robert Neilson.
1675:
289:" by conventional rules (independently of their
814:"Ueber Spectral‐Reactionen des Methylfurfurols"
768:
818:Berichte der Deutschen Chemischen Gesellschaft
917:
811:
718:’ test for pentoses (not to be confused with
617:The closure turns the carboxyl carbon into a
254:derivative with structure H–CHOH–C(=O)–(CHOH)
931:
924:
910:
812:Oshima, Kintaro; Tollens, B. (May 1901).
485:(E4P), which is used in the synthesis of
477:(R5P), which is used in the synthesis of
122:(R5P), which is used in the synthesis of
238:derivative with structure H–C(=O)–(CHOH)
698:composed of pentose sugars is called a
114:pentoses are important products of the
14:
1676:
734:to produce a colored compound; in the
905:
877:
791:
789:
705:
802:Library of Congress catalog 66-25695
683:In the cell, pentoses have a higher
854:Safety Scale Laboratory Experiments
607:, for having the same rings as the
595:–O– between the two carbons. This
242:–H. The most important example is
24:
786:
149:(–OH) each, connected by a single
25:
1695:
884:. Cengage Learning. p. 447.
857:. Cengage Learning. p. 358.
311:; therefore, eight (2) different
225:
189:: compounds with general formula
1658:
1657:
800:(2nd ed.). Allyn and Bacon.
659:
641:
624:
559:
543:
525:
509:
435:
419:
403:
387:
369:
353:
337:
321:
492:
296:
90:Pentoses are very important in
871:
844:
805:
756:
578:
258:–H (2-ketopentose) or H–(CHOH)
13:
1:
749:
738:with aniline acetate; and in
678:
657:
639:
541:
507:
461:, and the related molecule,
385:
319:
307:The aldopentoses have three
102:, and the related molecule,
7:
720:Tollens' silver-mirror test
10:
1700:
628:
496:
300:
1653:
1491:
1448:
1430:
1402:
1344:
1337:
1305:
1277:
1170:
1105:
1067:
1034:
1011:
1002:
971:
940:
878:Pavia, Donald L. (2005).
471:pentose phosphate pathway
116:pentose phosphate pathway
42:(simple sugar) with five
984:Cyclohexane conformation
830:10.1002/cber.19010340212
1477:Isomaltooligosaccharide
597:intramolecular reaction
481:and nucleic acids, and
1471:Galactooligosaccharide
465:, is a constituent of
277:, generally labelled "
106:, is a constituent of
1465:Fructooligosaccharide
483:erythrose 4-phosphate
132:erythrose 4-phosphate
27:5-Carbon simple sugar
736:aniline acetate test
487:aromatic amino acids
457:is a constituent of
98:is a constituent of
53:of many pentoses is
473:, most importantly
118:, most importantly
706:Tests for pentoses
475:ribose 5-phosphate
120:ribose 5-phosphate
1671:
1670:
1649:
1648:
1333:
1332:
798:Organic Chemistry
765:, Merriam-Webster
730:ring reacts with
676:
675:
668:
650:
587:interacts with a
576:
575:
568:
552:
534:
518:
452:
451:
444:
428:
412:
396:
378:
362:
346:
330:
142:carbons have one
87:is 150.13 g/mol.
16:(Redirected from
1691:
1661:
1660:
1452:oligosaccharides
1432:Tetrasaccharides
1342:
1341:
1057:Dihydroxyacetone
1009:
1008:
926:
919:
912:
903:
902:
896:
895:
875:
869:
868:
848:
842:
841:
824:(2): 1425–1426.
809:
803:
801:
793:
784:
780:
779:
772:
766:
760:
666:
663:
648:
645:
638:
637:
566:
563:
550:
547:
532:
529:
516:
513:
506:
505:
442:
439:
426:
423:
410:
407:
394:
391:
376:
373:
360:
357:
344:
341:
328:
325:
318:
317:
291:optical activity
288:
287:
282:
281:
221:
220:
219:
208:
207:
199:
198:
147:functional group
85:molecular weight
82:
81:
80:
72:
71:
63:
62:
51:chemical formula
21:
1699:
1698:
1694:
1693:
1692:
1690:
1689:
1688:
1674:
1673:
1672:
1667:
1645:
1506:Oat beta-glucan
1493:Polysaccharides
1487:
1450:
1444:
1426:
1398:
1329:
1323:Neuraminic acid
1301:
1273:
1166:
1101:
1063:
1030:
1004:Monosaccharides
998:
967:
936:
930:
900:
899:
892:
876:
872:
865:
849:
845:
810:
806:
794:
787:
777:
776:
773:
769:
761:
757:
752:
724:reducing sugars
708:
687:stability than
681:
665:
664:
647:
646:
633:
627:
612:tetrahydrofuran
581:
565:
564:
549:
548:
531:
530:
515:
514:
501:
495:
441:
440:
425:
424:
409:
408:
393:
392:
375:
374:
359:
358:
343:
342:
327:
326:
305:
299:
285:
284:
279:
278:
275:optical isomers
265:
261:
257:
241:
228:
218:
212:
211:
210:
206:
203:
202:
201:
197:
194:
193:
192:
190:
178:is 0, 1, or 2.
173:
166:
79:
76:
75:
74:
70:
67:
66:
65:
61:
58:
57:
56:
54:
28:
23:
22:
15:
12:
11:
5:
1697:
1687:
1686:
1669:
1668:
1666:
1665:
1654:
1651:
1650:
1647:
1646:
1644:
1643:
1638:
1637:
1636:
1631:
1621:
1616:
1611:
1606:
1604:Levan beta 2→6
1601:
1596:
1595:
1594:
1578:
1567:
1566:
1565:
1549:
1540:
1535:
1534:
1533:
1528:
1523:
1518:
1513:
1508:
1497:
1495:
1489:
1488:
1486:
1485:
1480:
1474:
1468:
1462:
1456:
1454:
1446:
1445:
1443:
1442:
1436:
1434:
1428:
1427:
1425:
1424:
1419:
1414:
1408:
1406:
1404:Trisaccharides
1400:
1399:
1397:
1396:
1391:
1386:
1381:
1376:
1371:
1366:
1361:
1356:
1350:
1348:
1339:
1335:
1334:
1331:
1330:
1328:
1327:
1326:
1325:
1315:
1309:
1307:
1303:
1302:
1300:
1299:
1298:
1297:
1292:
1290:Mannoheptulose
1283:
1281:
1275:
1274:
1272:
1271:
1270:
1269:
1264:
1259:
1251:
1250:
1249:
1244:
1239:
1234:
1224:
1223:
1222:
1217:
1212:
1207:
1202:
1197:
1192:
1187:
1176:
1174:
1168:
1167:
1165:
1164:
1163:
1162:
1152:
1151:
1150:
1145:
1137:
1136:
1135:
1130:
1125:
1120:
1111:
1109:
1103:
1102:
1100:
1099:
1098:
1097:
1089:
1088:
1087:
1082:
1073:
1071:
1065:
1064:
1062:
1061:
1060:
1059:
1051:
1050:
1049:
1047:Glyceraldehyde
1040:
1038:
1032:
1031:
1029:
1028:
1027:
1026:
1024:Glycolaldehyde
1017:
1015:
1006:
1000:
999:
997:
996:
991:
986:
981:
975:
973:
969:
968:
966:
965:
960:
955:
950:
944:
942:
938:
937:
929:
928:
921:
914:
906:
898:
897:
890:
870:
863:
843:
804:
785:
767:
754:
753:
751:
748:
732:phloroglucinol
707:
704:
680:
677:
674:
673:
656:
655:
626:
623:
585:carbonyl group
580:
577:
574:
573:
557:
540:
539:
523:
494:
491:
450:
449:
433:
417:
401:
384:
383:
367:
351:
335:
315:are possible.
309:chiral centers
298:
295:
263:
259:
255:
239:
227:
226:Classification
224:
213:
204:
195:
168:
162:
112:Phosphorylated
77:
68:
59:
40:monosaccharide
26:
9:
6:
4:
3:
2:
1696:
1685:
1682:
1681:
1679:
1664:
1656:
1655:
1652:
1642:
1639:
1635:
1632:
1630:
1627:
1626:
1625:
1622:
1620:
1617:
1615:
1612:
1610:
1607:
1605:
1602:
1600:
1599:Hemicellulose
1597:
1593:
1590:
1589:
1588:
1587:
1583:
1579:
1577:
1576:
1572:
1568:
1564:
1561:
1560:
1559:
1558:
1554:
1550:
1548:
1544:
1541:
1539:
1536:
1532:
1529:
1527:
1524:
1522:
1519:
1517:
1514:
1512:
1509:
1507:
1504:
1503:
1502:
1499:
1498:
1496:
1494:
1490:
1484:
1481:
1478:
1475:
1472:
1469:
1466:
1463:
1461:
1458:
1457:
1455:
1453:
1447:
1441:
1438:
1437:
1435:
1433:
1429:
1423:
1420:
1418:
1415:
1413:
1410:
1409:
1407:
1405:
1401:
1395:
1392:
1390:
1387:
1385:
1382:
1380:
1377:
1375:
1372:
1370:
1367:
1365:
1362:
1360:
1357:
1355:
1352:
1351:
1349:
1347:
1346:Disaccharides
1343:
1340:
1336:
1324:
1321:
1320:
1319:
1316:
1314:
1311:
1310:
1308:
1304:
1296:
1295:Sedoheptulose
1293:
1291:
1288:
1287:
1286:Ketoheptoses
1285:
1284:
1282:
1280:
1276:
1268:
1265:
1263:
1260:
1258:
1255:
1254:
1253:Deoxy sugars
1252:
1248:
1245:
1243:
1240:
1238:
1235:
1233:
1230:
1229:
1228:
1225:
1221:
1218:
1216:
1213:
1211:
1208:
1206:
1203:
1201:
1198:
1196:
1193:
1191:
1188:
1186:
1183:
1182:
1181:
1178:
1177:
1175:
1173:
1169:
1161:
1158:
1157:
1156:
1153:
1149:
1146:
1144:
1141:
1140:
1139:Ketopentoses
1138:
1134:
1131:
1129:
1126:
1124:
1121:
1119:
1116:
1115:
1114:Aldopentoses
1113:
1112:
1110:
1108:
1104:
1096:
1093:
1092:
1090:
1086:
1083:
1081:
1078:
1077:
1076:Aldotetroses
1075:
1074:
1072:
1070:
1066:
1058:
1055:
1054:
1052:
1048:
1045:
1044:
1042:
1041:
1039:
1037:
1033:
1025:
1022:
1021:
1019:
1018:
1016:
1014:
1010:
1007:
1005:
1001:
995:
992:
990:
987:
985:
982:
980:
977:
976:
974:
970:
964:
961:
959:
956:
954:
951:
949:
946:
945:
943:
939:
935:
934:carbohydrates
927:
922:
920:
915:
913:
908:
907:
904:
893:
887:
883:
882:
874:
866:
864:9781337517140
860:
856:
855:
847:
839:
835:
831:
827:
823:
819:
815:
808:
799:
792:
790:
782:
771:
764:
759:
755:
747:
745:
741:
737:
733:
729:
725:
721:
717:
713:
703:
701:
697:
692:
690:
686:
672:
662:
658:
654:
644:
640:
636:
632:
625:Deoxypentoses
622:
620:
619:chiral center
615:
613:
610:
606:
602:
598:
594:
590:
586:
572:
562:
558:
556:
546:
542:
538:
528:
524:
522:
512:
508:
504:
500:
490:
488:
484:
480:
476:
472:
468:
464:
460:
456:
448:
438:
434:
432:
422:
418:
416:
406:
402:
400:
390:
386:
382:
372:
368:
366:
356:
352:
350:
340:
336:
334:
324:
320:
316:
314:
313:stereoisomers
310:
304:
294:
292:
276:
272:
271:stereoisomers
267:
262:–C(=O)–(CHOH)
253:
249:
245:
237:
233:
223:
217:
188:
184:
183:deoxypentoses
179:
177:
172:
167:–C(=O)–(CHOH)
165:
160:
156:
152:
148:
145:
139:
137:
133:
129:
128:nucleic acids
125:
121:
117:
113:
109:
105:
101:
97:
93:
88:
86:
52:
48:
45:
41:
37:
33:
19:
1580:
1569:
1551:
1483:Maltodextrin
1364:Isomaltulose
1155:Deoxy sugars
1106:
1091:Ketotetrose
994:Mutarotation
880:
873:
853:
846:
821:
817:
807:
797:
770:
758:
709:
693:
682:
634:
616:
609:cyclic ether
593:ether bridge
582:
502:
493:Ketopentoses
453:
306:
297:Aldopentoses
268:
248:ketopentoses
232:aldopentoses
229:
215:
182:
180:
175:
170:
163:
140:
92:biochemistry
89:
83:, and their
35:
29:
1641:Xanthan gum
1629:Amylopectin
1501:Beta-glucan
1412:Maltotriose
1227:Ketohexoses
1180:Aldohexoses
1160:Deoxyribose
1095:Erythrulose
1053:Ketotriose
1043:Aldotriose
740:Bial's test
712:chromophore
671:Deoxyribose
653:Deoxyribose
631:Deoxy sugar
579:Cyclic form
479:nucleotides
463:deoxyribose
187:deoxyribose
136:amino acids
124:nucleotides
104:deoxyribose
18:Aldopentose
1417:Melezitose
1359:Isomaltose
1354:Cellobiose
1020:Aldodiose
891:0534408338
750:References
679:Properties
629:See also:
497:See also:
301:See also:
185:, such as
174:–H, where
1571:Galactose
1526:Cellulose
1516:Sizofiran
1440:Stachyose
1422:Raffinose
1389:Trehalose
1374:Lactulose
1195:Galactose
1118:Arabinose
1080:Erythrose
932:Types of
838:0365-9496
685:metabolic
605:furanoses
599:yields a
399:Arabinose
333:Arabinose
32:chemistry
1684:Pentoses
1678:Category
1663:Category
1592:Glycogen
1575:Galactan
1553:Fructose
1538:Chitosan
1511:Lentinan
1460:Acarbose
1394:Turanose
1338:Multiple
1279:Heptoses
1267:Rhamnose
1262:Fuculose
1247:Tagatose
1232:Fructose
1148:Xylulose
1143:Ribulose
1107:Pentoses
1069:Tetroses
972:Geometry
963:Pyranose
958:Furanose
728:furfural
700:pentosan
589:hydroxyl
571:Xylulose
555:Ribulose
537:Xylulose
521:Ribulose
236:aldehyde
159:hydrogen
155:carbonyl
144:hydroxyl
1634:Amylose
1582:Glucose
1557:Fructan
1547:Dextran
1543:Dextrin
1521:Zymosan
1384:Sucrose
1379:Maltose
1369:Lactose
1318:Nonoses
1313:Octoses
1306:Above 7
1242:Sorbose
1237:Psicose
1215:Mannose
1200:Glucose
1190:Altrose
1172:Hexoses
1085:Threose
1036:Trioses
941:General
781:-Ribose
763:Pentose
744:orcinol
742:, with
726:), the
716:Tollens
696:polymer
689:hexoses
246:. The
49:. The
36:pentose
1624:Starch
1619:Pectin
1614:Mannan
1609:Lignin
1586:Glucan
1563:Inulin
1531:Chitin
1257:Fucose
1220:Talose
1205:Gulose
1185:Allose
1133:Xylose
1128:Ribose
1123:Lyxose
1013:Dioses
989:Epimer
979:Anomer
953:Ketose
948:Aldose
888:
861:
836:
601:cyclic
499:ketose
455:Ribose
447:Xylose
431:Ribose
415:Lyxose
381:Xylose
365:Ribose
349:Lyxose
303:aldose
283:" or "
252:ketone
244:ribose
130:, and
96:Ribose
44:carbon
1479:(IMO)
1473:(GOS)
1467:(FOS)
1449:Other
1210:Idose
714:. In
47:atoms
38:is a
886:ISBN
859:ISBN
834:ISSN
722:for
230:The
151:bond
126:and
34:, a
826:doi
467:DNA
459:RNA
293:).
108:DNA
100:RNA
30:In
1680::
1584:/
1573:/
1555:/
1545:/
832:.
822:34
820:.
816:.
788:^
702:.
694:A
691:.
614:.
489:.
214:5-
205:10
169:4-
138:.
110:.
94:.
69:10
925:e
918:t
911:v
894:.
867:.
840:.
828::
778:D
774:"
669:-
667:L
651:-
649:D
569:-
567:L
553:-
551:L
535:-
533:D
519:-
517:D
445:-
443:L
429:-
427:L
413:-
411:L
397:-
395:L
379:-
377:D
363:-
361:D
347:-
345:D
331:-
329:D
286:L
280:D
264:2
260:2
256:3
240:4
216:y
209:O
200:H
196:5
191:C
176:x
171:x
164:x
78:5
73:O
64:H
60:5
55:C
20:)
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