1099:
1117:
865:- prefixes are also used with other monosaccharides, to distinguish two particular stereoisomers that are mirror-images of each other. For this purpose, one considers the chiral carbon that is furthest removed from the C=O group. Its four bonds must connect to −H, −OH, −C(OH)H, and the rest of the molecule. If the molecule can be rotated in space so that the directions of those four groups match those of the analog groups in
763:. For example, there are 16 distinct aldohexose stereoisomers, but the name "glucose" means a specific pair of mirror-image aldohexoses. In the Fischer projection, one of the two glucose isomers has the hydroxyl at left on C3, and at right on C4 and C5; while the other isomer has the reversed pattern. These specific monosaccharide names have conventional three-letter abbreviations, like "Glu" for glucose and "Thr" for
3238:
2466:
2456:
77:
1028:
1036:
179:
36:
1014:
835:
722:, and −(C=O)H. Therefore, it exists as two stereoisomers whose molecules are mirror images of each other (like a left and a right glove). Monosaccharides with four or more carbons may contain multiple chiral carbons, so they typically have more than two stereoisomers. The number of distinct stereoisomers with the same diagram is bounded by 2, where
223:
658:
A more general nomenclature for open-chain monosaccharides combines a Greek prefix to indicate the number of carbons (tri-, tetr-, pent-, hex-, etc.) with the suffixes "-ose" for aldoses and "-ulose" for ketoses. In the latter case, if the carbonyl is not at position 2, its position is then indicated
741:
Most stereoisomers are themselves chiral (distinct from their mirror images). In the
Fischer projection, two mirror-image isomers differ by having the positions of all chiral hydroxyls reversed right-to-left. Mirror-image isomers are chemically identical in non-chiral environments, but usually have
1043:
For many monosaccharides (including glucose), the cyclic forms predominate, in the solid state and in solutions, and therefore the same name commonly is used for the open- and closed-chain isomers. Thus, for example, the term "glucose" may signify glucofuranose, glucopyranose, the open-chain form,
737:
of an acyclic monosaccharide so that the handedness of each chiral carbon is well specified. Each stereoisomer of a simple open-chain monosaccharide can be identified by the positions (right or left) in the
Fischer diagram of the chiral hydroxyls (the hydroxyls attached to the chiral carbons).
745:
While most stereoisomers can be arranged in pairs of mirror-image forms, there are some non-chiral stereoisomers that are identical to their mirror images, in spite of having chiral centers. This happens whenever the molecular graph is symmetrical, as in the 3-ketopentoses
925:- prefixes do not indicate the direction of rotation of polarized light, which is a combined effect of the arrangement at all chiral centers. However, the two enantiomers will always rotate the light in opposite directions, by the same amount. See also
783:> 2 is the number of carbons. These are also referred to as epimers which have the different arrangement of −OH and −H groups at the asymmetric or chiral carbon atoms (this does not apply to those carbons having the carbonyl functional group).
754:
H, and the two halves are mirror images of each other. In that case, mirroring is equivalent to a half-turn rotation. For this reason, there are only three distinct 3-ketopentose stereoisomers, even though the molecule has two chiral carbons.
774:
asymmetrical carbons has 2 stereoisomers. The number of open chain stereoisomers for an aldose monosaccharide is larger by one than that of a ketose monosaccharide of the same length. Every ketose will have 2 stereoisomers where
758:
Distinct stereoisomers that are not mirror-images of each other usually have different chemical properties, even in non-chiral environments. Therefore, each mirror pair and each non-chiral stereoisomer may be given a specific
1051:
center at the carbonyl-bearing carbon. The −OH group that replaces the carbonyl's oxygen may end up in two distinct positions relative to the ring's midplane. Thus each open-chain monosaccharide yields two cyclic isomers
1086:. In this conformation, the α-isomer has the −OH of the anomeric carbon in an axial position, whereas the β-isomer has the −OH of the anomeric carbon in equatorial position (considering
1082:
below the plane of the carbon atoms, while the β-isomer has the −OH of the anomeric carbon above the plane. Pyranoses typically adopt a chair conformation, similar to that of
652:
group, a carbonyl −(C=O)− between two carbons; then it is formally a ketone, and is termed a ketose. Ketoses of biological interest usually have the carbonyl at position 2.
1323:
703:. In a simple open-chain monosaccharide, every carbon is chiral except the first and the last atoms of the chain, and (in ketoses) the carbon with the keto group.
625:
along the backbone, starting from the end that is closest to the C=O group. Monosaccharides are the simplest units of carbohydrates and the simplest form of sugar.
955:
reaction between the carbonyl group and one of the hydroxyl groups of the same molecule. The reaction creates a ring of carbon atoms closed by one bridging
2207:
2130:
990:
may form a hemiacetal linkage between the aldehyde group on carbon 1 and the hydroxyl on carbon 4, yielding a molecule with a 5-membered ring, called
986:, the simplest compounds with the same carbon-oxygen ring (although they lack the double bonds of these two molecules). For example, the aldohexose
2502:
2077:
967:
group, depending on whether the linear form was an aldose or a ketose. The reaction is easily reversed, yielding the original open-chain form.
699:(connected to four distinct molecular sub-structures). Those four bonds can have any of two configurations in space distinguished by their
2030:
2102:
2025:
2316:
2045:
1998:
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273:
160:
63:
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1393:
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49:
1366:
141:
98:
1972:
113:
1876:
324:
1906:
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used in everyday vernacular is itself a disaccharide sucrose comprising one molecule of each of the two monosaccharides
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2140:
2060:
2055:
2040:
1210:
760:
463:
120:
710:) has no stereogenic center, and therefore exists as a single stereoisomer. The other triose, the aldose H(C=O)(CHOH)
2202:
2182:
2162:
1768:
1309:; Anet, E. F. L. J. (1972). "Chapter 4: Mutarotations and Actions of Acids and Bases". In Pigman and Horton (ed.).
87:
2469:
1098:
127:
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2562:
2082:
2050:
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1116:
233:
655:
The various classifications above can be combined, resulting in names such as "aldohexose" and "ketotriose".
3055:
2363:
2177:
2035:
1633:
1056:), denoted by the prefixes α- and β-. The molecule can change between these two forms by a process called
109:
3241:
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2217:
926:
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2227:
2167:
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1673:
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3182:
1728:
1643:
1531:
2135:
2020:
1977:
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as it passes through it, even in solution. The two stereoisomers are identified with the prefixes
197:
55:
2395:
2222:
2112:
1778:
1069:
730:
692:
545:. Monosaccharides with eight or more carbons are rarely observed as they are quite unstable. In
521:
Glucose, used as an energy source and for the synthesis of starch, glycogen and cellulose, is a
248:
1060:, that consists in a reversal of the ring-forming reaction followed by another ring formation.
691:, whose molecules differ in spatial orientation. This happens only if the molecule contains a
294:
2326:
2192:
2107:
1581:
1262:
1252:
791:
Like many chiral molecules, the two stereoisomers of glyceraldehyde will gradually rotate the
447:
718:), has one chiral carbon—the central one, number 2—which is bonded to groups −H, −OH, −C(OH)H
244:
2635:
2390:
2232:
2154:
1788:
1586:
1337:
792:
734:
707:
562:
546:
473:
134:
3084:
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3010:
2901:
2373:
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2003:
1982:
1896:
1196:
1079:
948:
796:
684:
573:. Therefore, the molecular structure of a simple monosaccharide can be written as H(CHOH)
1356:
McMurry, John. Organic
Chemistry. 7th ed. Belmont, CA: Thomson Brooks/Cole, 2008. Print.
1027:
431:
forms, all with the same chemical formula. For instance, galactose and glucose are both
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2625:
2602:
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2336:
2300:
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1962:
1952:
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1485:
1412:
1379:
1215:
1176:
1035:
818:
715:
538:
385:
290:
1013:
970:
In these cyclic forms, the ring usually has five or six atoms. These forms are called
898:- prefixes specifies the configuration at the carbon atom that is second from bottom:
3256:
3177:
3094:
2982:
2873:
2426:
2090:
1891:
1886:
1733:
1618:
1596:
1591:
1521:
1225:
1186:
1148:
999:
994:. The same reaction can take place between carbons 1 and 5 to form a molecule with a
991:
542:
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2924:
2572:
2512:
2285:
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2197:
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2013:
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1803:
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1601:
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828:
688:
369:
317:
17:
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organic solids. Contrary to their name (sugars), only some monosaccharides have a
3219:
3207:
3079:
2990:
2738:
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2431:
2351:
2341:
2258:
2248:
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2008:
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1606:
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1516:
1511:
1480:
1328:
1158:
1153:
1142:
1083:
1068:
The stereochemical structure of a cyclic monosaccharide can be represented in a
1048:
469:
397:
76:
779:> 2 is the number of carbons. Every aldose will have 2 stereoisomers where
2995:
2937:
2932:
2805:
2758:
2346:
2331:
2268:
1957:
1940:
1901:
1823:
1818:
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1613:
1546:
1541:
1526:
1501:
1220:
960:
700:
443:
439:
432:
1332:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
557:
Simple monosaccharides have a linear and unbranched carbon skeleton with one
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3104:
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1506:
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964:
389:
365:
340:
1313:. Vol. 1A (2nd ed.). San Diego: Academic Press. pp. 165–194.
1371:
1248:
Monosaccharides : their chemistry and their roles in natural products
3170:
3131:
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2721:
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1845:
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1191:
1138:
A large number of biologically important modified monosaccharides exist:
975:
971:
641:
566:
558:
420:
361:
947:
A monosaccharide often switches from the acyclic (open-chain) form to a
3212:
3192:
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3135:
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3121:
3099:
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2957:
2947:
2857:
2820:
2815:
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2647:
2410:
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1967:
1935:
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1658:
1468:
1463:
1458:
1441:
1007:
1003:
987:
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427:, except those at the end of the chain. This gives rise to a number of
381:
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313:
3202:
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3187:
3164:
3141:
3109:
2896:
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2835:
2798:
2783:
2763:
2750:
2711:
2706:
2701:
2614:
2567:
2557:
2531:
2526:
2368:
2356:
1828:
1773:
1446:
1053:
956:
687:(same chain length and same carbonyl position) may still be distinct
649:
645:
637:
534:
533:, respectively) are pentose sugars. Examples of heptoses include the
522:
511:
499:
495:
428:
416:
393:
549:
monosaccharides exist as rings if they have more than four carbons.
2788:
2591:
1813:
1748:
1638:
1563:
1402:
1034:
1026:
1012:
983:
979:
833:
435:, but have different physical structures and chemical properties.
353:(though not all molecules with this formula are monosaccharides).
328:
309:
742:
very different biochemical properties and occurrences in nature.
1017:
Conversion between the furanose, acyclic, and pyranose forms of
570:
2484:
1375:
1881:
1251:. Robert J. Ferrier. Chichester: Wiley & Sons. p. 4.
530:
526:
216:
172:
70:
29:
1072:. In this diagram, the α-isomer for the pyranose form of a
706:
For example, the triketose H(CHOH)(C=O)(CHOH)H (glycerone,
621:
By convention, the carbon atoms are numbered from 1 to
450:
to provide energy to living organisms. Maltose is the
240:
193:
490:≥ 3. Monosaccharides can be classified by the number
196:
by adding general information and discuss at the
3070:
3027:
3009:
2981:
2923:
2916:
2884:
2856:
2749:
2684:
2646:
2613:
2590:
2581:
2550:
2519:
2419:
2309:
2241:
2153:
2123:
1991:
1928:
1919:
1859:
1697:
1562:
1555:
1494:
1419:
1002:. Cyclic forms with a seven-atom ring (the same of
871:-glyceraldehyde's C2, then the isomer receives the
438:The monosaccharide glucose plays a pivotal role in
101:. Unsourced material may be challenged and removed.
659:by a numeric infix. So, for example, H(C=O)(CHOH)
821:(rotates the polarization axis clockwise), while
442:, where the chemical energy is extracted through
1245:Collins, Peter M.; Ferrier, Robert J. (1995).
2496:
1387:
1311:The Carbohydrates: Chemistry and Biochemistry
368:. Monosaccharides are the building blocks of
8:
904:- if the hydroxyl is on the right side, and
2208:Slavery in the British and French Caribbean
628:If the carbonyl is at position 1 (that is,
569:(OH) group on each of the remaining carbon
343:. Most monosaccharides have the formula (CH
64:Learn how and when to remove these messages
2920:
2587:
2503:
2489:
2481:
1925:
1559:
1394:
1380:
1372:
644:. In that case, the compound is termed an
27:Simple sugars such as glucose and fructose
943:of monosaccharides (hemiacetal formation)
274:Learn how and when to remove this message
161:Learn how and when to remove this message
1237:
1094:
811:-, according to the sense of rotation:
726:is the total number of chiral carbons.
1031:Pyranose forms of some pentose sugars
877:- prefix. Otherwise, it receives the
695:, specifically a carbon atom that is
636:is zero), the molecule begins with a
188:one specialized aspect of the subject
7:
1039:Pyranose forms of some hexose sugars
959:atom. The resulting molecule has a
683:Two monosaccharides with equivalent
640:group H(C=O)− and is technically an
599:; so that its elemental formula is C
356:Examples of monosaccharides include
99:adding citations to reliable sources
733:is a systematic way of drawing the
247:in tone and meet Knowledge (XXG)'s
1329:Compendium of Chemical Terminology
1006:), rarely encountered, are called
25:
2317:Australian Aboriginal sweet foods
1413:List of sugars and sugar products
770:Generally, a monosaccharide with
45:This article has multiple issues.
3237:
3236:
2465:
2464:
2455:
2454:
1115:
1097:
787:Configuration of monosaccharides
663:H is pentose, H(CHOH)(C=O)(CHOH)
648:. Otherwise, the molecule has a
221:
177:
75:
34:
1078:-aldohexose has the −OH of the
978:, respectively—by analogy with
886:In the Fischer projection, the
831:(rotates it counterclockwise).
86:needs additional citations for
53:or discuss these issues on the
1:
1367:Nomenclature of Carbohydrates
910:- if it is on the left side.
525:. Ribose and deoxyribose (in
472:), monosaccharides have this
186:This article focuses only on
1287:. Royal Society of Chemistry
553:Linear-chain monosaccharides
308:, are the simplest forms of
1211:Monosaccharide nomenclature
1044:or a mixture of the three.
667:H is pentulose, and H(CHOH)
468:With few exceptions (e.g.,
464:Monosaccharide nomenclature
3284:
2203:Reciprocity Treaty of 1875
2183:Demerara rebellion of 1823
2163:1811 German Coast uprising
1769:Non-centrifugal cane sugar
1047:Cyclization creates a new
461:
458:Structure and nomenclature
454:of two glucose molecules.
312:and the most basic units (
3232:
2450:
1410:
2563:Cyclohexane conformation
1629:High-fructose corn syrup
1285:Chemistry for Biologists
679:Open-chain stereoisomers
3056:Isomaltooligosaccharide
2178:Colonial molasses trade
1634:High-maltose corn syrup
1342:10.1351/goldbook.H02749
486:, where conventionally
3268:Carbohydrate chemistry
3050:Galactooligosaccharide
2438:Pure, White and Deadly
2218:Sugar Duties Acts 1846
2124:By region (historical)
1334:Haworth representation
1040:
1032:
1024:
850:
793:polarization direction
452:dehydration condensate
304:: sugar), also called
3044:Fructooligosaccharide
2228:Taiwan Sugar Railways
2168:Amelioration Act 1798
1173:Sulfosugars such as:
1092:-aldohexose sugars).
1038:
1030:
1016:
953:nucleophilic addition
837:
419:atom that supports a
1907:Unrefined sweeteners
1729:Crystalline fructose
1644:Inverted sugar syrup
1307:Pigman, William Ward
498:atoms they contain:
241:improve this article
194:improve this article
95:improve this article
1992:By region (current)
1892:Sugar confectionery
827:-glyceraldehyde is
817:-glyceraldehyde is
761:monosaccharide name
675:H is pent-3-ulose.
18:Simple carbohydrate
2396:Sweetened beverage
2223:Sugar Intervention
2131:Danish West Indies
2113:U.S. Sugar Program
1872:Cotton candy floss
1779:Plantation Reserve
1674:Steen's cane syrup
1167:-acetylglucosamine
1070:Haworth projection
1064:Haworth projection
1041:
1033:
1025:
851:
731:Fischer projection
693:stereogenic center
3250:
3249:
3228:
3227:
2912:
2911:
2478:
2477:
2327:Blood sugar level
2193:Leith Sugar House
2149:
2148:
2108:Sugar Association
1915:
1914:
1877:Maple sugar foods
1582:Barley malt syrup
1405:as food commodity
547:aqueous solutions
448:citric acid cycle
323:They are usually
316:) from which all
284:
283:
276:
266:
265:
249:quality standards
215:
214:
171:
170:
163:
145:
68:
16:(Redirected from
3275:
3240:
3239:
3031:oligosaccharides
3011:Tetrasaccharides
2921:
2636:Dihydroxyacetone
2588:
2505:
2498:
2491:
2482:
2468:
2467:
2458:
2457:
2391:Sugar substitute
2233:Triangular trade
1926:
1587:Brown rice syrup
1560:
1396:
1389:
1382:
1373:
1344:
1321:
1315:
1314:
1303:
1297:
1296:
1294:
1292:
1277:
1271:
1270:
1242:
1183:Others such as:
1127:
1126:
1119:
1109:
1108:
1101:
1091:
1090:
1077:
1076:
1022:
1021:
997:
951:form, through a
942:
941:
931:
930:
924:
923:
918:
917:
909:
908:
903:
902:
897:
896:
891:
890:
882:
881:
876:
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869:
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863:
858:
857:
848:
847:
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841:
826:
825:
816:
815:
810:
809:
804:
803:
735:skeletal formula
708:dihydroxyacetone
685:molecular graphs
598:
563:functional group
518:(7), and so on.
474:chemical formula
411:
410:
405:
404:
364:(levulose), and
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110:"Monosaccharide"
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38:
37:
30:
21:
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3277:
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3273:
3272:
3263:Monosaccharides
3253:
3252:
3251:
3246:
3224:
3085:Oat beta-glucan
3072:Polysaccharides
3066:
3029:
3023:
3005:
2977:
2908:
2902:Neuraminic acid
2880:
2852:
2745:
2680:
2642:
2609:
2583:Monosaccharides
2577:
2546:
2515:
2509:
2479:
2474:
2446:
2415:
2374:Sugar addiction
2305:
2296:Sugar sculpture
2237:
2145:
2119:
2096:Tate & Lyle
2087:United Kingdom
2004:Bundaberg Sugar
1987:
1983:Sugar marketing
1911:
1897:Sugarcane juice
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1281:"Carbohydrates"
1279:
1278:
1274:
1259:
1244:
1243:
1239:
1234:
1207:
1197:glucuronic acid
1136:
1129:
1124:
1123:
1120:
1111:
1106:
1105:
1102:
1088:
1087:
1080:anomeric carbon
1074:
1073:
1066:
1019:
1018:
995:
945:
939:
938:
928:
927:
921:
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797:polarized light
789:
753:
749:
721:
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681:
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611:
604:
586:
584:
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555:
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402:
401:
386:polysaccharides
352:
346:
287:Monosaccharides
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104:
102:
92:
80:
39:
35:
28:
23:
22:
15:
12:
11:
5:
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3254:
3248:
3247:
3245:
3244:
3233:
3230:
3229:
3226:
3225:
3223:
3222:
3217:
3216:
3215:
3210:
3200:
3195:
3190:
3185:
3183:Levan beta 2→6
3180:
3175:
3174:
3173:
3157:
3146:
3145:
3144:
3128:
3119:
3114:
3113:
3112:
3107:
3102:
3097:
3092:
3087:
3076:
3074:
3068:
3067:
3065:
3064:
3059:
3053:
3047:
3041:
3035:
3033:
3025:
3024:
3022:
3021:
3015:
3013:
3007:
3006:
3004:
3003:
2998:
2993:
2987:
2985:
2983:Trisaccharides
2979:
2978:
2976:
2975:
2970:
2965:
2960:
2955:
2950:
2945:
2940:
2935:
2929:
2927:
2918:
2914:
2913:
2910:
2909:
2907:
2906:
2905:
2904:
2894:
2888:
2886:
2882:
2881:
2879:
2878:
2877:
2876:
2871:
2869:Mannoheptulose
2862:
2860:
2854:
2853:
2851:
2850:
2849:
2848:
2843:
2838:
2830:
2829:
2828:
2823:
2818:
2813:
2803:
2802:
2801:
2796:
2791:
2786:
2781:
2776:
2771:
2766:
2755:
2753:
2747:
2746:
2744:
2743:
2742:
2741:
2731:
2730:
2729:
2724:
2716:
2715:
2714:
2709:
2704:
2699:
2690:
2688:
2682:
2681:
2679:
2678:
2677:
2676:
2668:
2667:
2666:
2661:
2652:
2650:
2644:
2643:
2641:
2640:
2639:
2638:
2630:
2629:
2628:
2626:Glyceraldehyde
2619:
2617:
2611:
2610:
2608:
2607:
2606:
2605:
2603:Glycolaldehyde
2596:
2594:
2585:
2579:
2578:
2576:
2575:
2570:
2565:
2560:
2554:
2552:
2548:
2547:
2545:
2544:
2539:
2534:
2529:
2523:
2521:
2517:
2516:
2510:
2508:
2507:
2500:
2493:
2485:
2476:
2475:
2473:
2472:
2462:
2451:
2448:
2447:
2445:
2444:
2443:
2442:
2429:
2423:
2421:
2417:
2416:
2414:
2413:
2408:
2403:
2398:
2393:
2388:
2387:
2386:
2384:Residual sugar
2379:Sugars in wine
2376:
2371:
2366:
2364:Health effects
2361:
2360:
2359:
2354:
2349:
2339:
2337:Flavored syrup
2334:
2329:
2324:
2319:
2313:
2311:
2307:
2306:
2304:
2303:
2301:Treacle mining
2298:
2293:
2288:
2283:
2282:
2281:
2271:
2266:
2261:
2256:
2251:
2245:
2243:
2239:
2238:
2236:
2235:
2230:
2225:
2220:
2215:
2210:
2205:
2200:
2195:
2190:
2185:
2180:
2175:
2170:
2165:
2159:
2157:
2151:
2150:
2147:
2146:
2144:
2143:
2138:
2133:
2127:
2125:
2121:
2120:
2118:
2117:
2116:
2115:
2110:
2100:
2099:
2098:
2093:
2085:
2080:
2075:
2074:
2073:
2071:Tongaat Hulett
2068:
2058:
2053:
2048:
2043:
2038:
2033:
2028:
2023:
2018:
2017:
2016:
2011:
2006:
1995:
1993:
1989:
1988:
1986:
1985:
1980:
1975:
1970:
1965:
1963:Sugarcane mill
1960:
1955:
1950:
1949:
1948:
1938:
1932:
1930:
1923:
1917:
1916:
1913:
1912:
1910:
1909:
1904:
1899:
1894:
1889:
1884:
1879:
1874:
1869:
1863:
1861:
1857:
1856:
1854:
1853:
1848:
1843:
1838:
1833:
1832:
1831:
1826:
1821:
1816:
1811:
1806:
1796:
1791:
1786:
1781:
1776:
1771:
1766:
1761:
1756:
1754:Molasses sugar
1751:
1746:
1741:
1736:
1731:
1726:
1721:
1716:
1715:
1714:
1701:
1699:
1695:
1694:
1692:
1691:
1686:
1681:
1676:
1671:
1666:
1661:
1656:
1651:
1646:
1641:
1636:
1631:
1626:
1621:
1616:
1611:
1610:
1609:
1604:
1599:
1589:
1584:
1579:
1574:
1572:List of syrups
1568:
1566:
1557:
1553:
1552:
1550:
1549:
1544:
1539:
1534:
1529:
1524:
1519:
1514:
1509:
1504:
1498:
1496:
1492:
1491:
1489:
1488:
1486:Reducing sugar
1483:
1478:
1477:
1476:
1471:
1466:
1461:
1451:
1450:
1449:
1444:
1439:
1434:
1427:Monosaccharide
1423:
1421:
1417:
1416:
1411:
1408:
1407:
1401:
1399:
1398:
1391:
1384:
1376:
1370:
1369:
1362:
1361:External links
1359:
1358:
1357:
1352:
1349:
1346:
1345:
1316:
1298:
1272:
1257:
1236:
1235:
1233:
1230:
1229:
1228:
1223:
1218:
1216:Reducing sugar
1213:
1206:
1203:
1202:
1201:
1200:
1199:
1194:
1189:
1181:
1180:
1179:
1177:sulfoquinovose
1171:
1170:
1169:
1161:
1156:
1151:
1135:
1132:
1131:
1130:
1128:-Glucopyranose
1121:
1114:
1112:
1110:-Glucopyranose
1103:
1096:
1065:
1062:
944:
936:
913:Note that the
819:dextrorotatory
788:
785:
751:
747:
719:
716:glyceraldehyde
711:
680:
677:
672:
668:
664:
660:
613:
606:
600:
580:
574:
554:
551:
539:mannoheptulose
481:
477:
459:
456:
348:
344:
282:
281:
264:
263:
229:
227:
220:
213:
212:
206:September 2013
185:
183:
176:
169:
168:
83:
81:
74:
69:
43:
42:
40:
33:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
3280:
3269:
3266:
3264:
3261:
3260:
3258:
3243:
3235:
3234:
3231:
3221:
3218:
3214:
3211:
3209:
3206:
3205:
3204:
3201:
3199:
3196:
3194:
3191:
3189:
3186:
3184:
3181:
3179:
3178:Hemicellulose
3176:
3172:
3169:
3168:
3167:
3166:
3162:
3158:
3156:
3155:
3151:
3147:
3143:
3140:
3139:
3138:
3137:
3133:
3129:
3127:
3123:
3120:
3118:
3115:
3111:
3108:
3106:
3103:
3101:
3098:
3096:
3093:
3091:
3088:
3086:
3083:
3082:
3081:
3078:
3077:
3075:
3073:
3069:
3063:
3060:
3057:
3054:
3051:
3048:
3045:
3042:
3040:
3037:
3036:
3034:
3032:
3026:
3020:
3017:
3016:
3014:
3012:
3008:
3002:
2999:
2997:
2994:
2992:
2989:
2988:
2986:
2984:
2980:
2974:
2971:
2969:
2966:
2964:
2961:
2959:
2956:
2954:
2951:
2949:
2946:
2944:
2941:
2939:
2936:
2934:
2931:
2930:
2928:
2926:
2925:Disaccharides
2922:
2919:
2915:
2903:
2900:
2899:
2898:
2895:
2893:
2890:
2889:
2887:
2883:
2875:
2874:Sedoheptulose
2872:
2870:
2867:
2866:
2865:Ketoheptoses
2864:
2863:
2861:
2859:
2855:
2847:
2844:
2842:
2839:
2837:
2834:
2833:
2832:Deoxy sugars
2831:
2827:
2824:
2822:
2819:
2817:
2814:
2812:
2809:
2808:
2807:
2804:
2800:
2797:
2795:
2792:
2790:
2787:
2785:
2782:
2780:
2777:
2775:
2772:
2770:
2767:
2765:
2762:
2761:
2760:
2757:
2756:
2754:
2752:
2748:
2740:
2737:
2736:
2735:
2732:
2728:
2725:
2723:
2720:
2719:
2718:Ketopentoses
2717:
2713:
2710:
2708:
2705:
2703:
2700:
2698:
2695:
2694:
2693:Aldopentoses
2692:
2691:
2689:
2687:
2683:
2675:
2672:
2671:
2669:
2665:
2662:
2660:
2657:
2656:
2655:Aldotetroses
2654:
2653:
2651:
2649:
2645:
2637:
2634:
2633:
2631:
2627:
2624:
2623:
2621:
2620:
2618:
2616:
2612:
2604:
2601:
2600:
2598:
2597:
2595:
2593:
2589:
2586:
2584:
2580:
2574:
2571:
2569:
2566:
2564:
2561:
2559:
2556:
2555:
2553:
2549:
2543:
2540:
2538:
2535:
2533:
2530:
2528:
2525:
2524:
2522:
2518:
2514:
2513:carbohydrates
2506:
2501:
2499:
2494:
2492:
2487:
2486:
2483:
2471:
2463:
2461:
2453:
2452:
2449:
2440:
2439:
2435:
2434:
2433:
2430:
2428:
2427:Robert Lustig
2425:
2424:
2422:
2418:
2412:
2409:
2407:
2404:
2402:
2399:
2397:
2394:
2392:
2389:
2385:
2382:
2381:
2380:
2377:
2375:
2372:
2370:
2367:
2365:
2362:
2358:
2355:
2353:
2350:
2348:
2345:
2344:
2343:
2340:
2338:
2335:
2333:
2330:
2328:
2325:
2323:
2320:
2318:
2315:
2314:
2312:
2308:
2302:
2299:
2297:
2294:
2292:
2289:
2287:
2284:
2280:
2277:
2276:
2275:
2272:
2270:
2267:
2265:
2262:
2260:
2257:
2255:
2252:
2250:
2247:
2246:
2244:
2240:
2234:
2231:
2229:
2226:
2224:
2221:
2219:
2216:
2214:
2211:
2209:
2206:
2204:
2201:
2199:
2196:
2194:
2191:
2189:
2186:
2184:
2181:
2179:
2176:
2174:
2171:
2169:
2166:
2164:
2161:
2160:
2158:
2156:
2152:
2142:
2139:
2137:
2134:
2132:
2129:
2128:
2126:
2122:
2114:
2111:
2109:
2106:
2105:
2104:
2103:United States
2101:
2097:
2094:
2092:
2091:British Sugar
2089:
2088:
2086:
2084:
2081:
2079:
2076:
2072:
2069:
2067:
2064:
2063:
2062:
2059:
2057:
2054:
2052:
2049:
2047:
2044:
2042:
2039:
2037:
2034:
2032:
2029:
2027:
2024:
2022:
2019:
2015:
2012:
2010:
2007:
2005:
2002:
2001:
2000:
1997:
1996:
1994:
1990:
1984:
1981:
1979:
1976:
1974:
1971:
1969:
1966:
1964:
1961:
1959:
1956:
1954:
1951:
1947:
1944:
1943:
1942:
1939:
1937:
1934:
1933:
1931:
1927:
1924:
1922:
1918:
1908:
1905:
1903:
1900:
1898:
1895:
1893:
1890:
1888:
1887:Sugar alcohol
1885:
1883:
1880:
1878:
1875:
1873:
1870:
1868:
1865:
1864:
1862:
1858:
1852:
1849:
1847:
1844:
1842:
1839:
1837:
1834:
1830:
1827:
1825:
1822:
1820:
1817:
1815:
1812:
1810:
1807:
1805:
1802:
1801:
1800:
1797:
1795:
1792:
1790:
1787:
1785:
1782:
1780:
1777:
1775:
1772:
1770:
1767:
1765:
1762:
1760:
1757:
1755:
1752:
1750:
1747:
1745:
1742:
1740:
1737:
1735:
1732:
1730:
1727:
1725:
1722:
1720:
1717:
1713:
1712:
1708:
1707:
1706:
1703:
1702:
1700:
1696:
1690:
1687:
1685:
1682:
1680:
1677:
1675:
1672:
1670:
1667:
1665:
1662:
1660:
1657:
1655:
1652:
1650:
1647:
1645:
1642:
1640:
1637:
1635:
1632:
1630:
1627:
1625:
1622:
1620:
1619:Glucose syrup
1617:
1615:
1612:
1608:
1605:
1603:
1600:
1598:
1597:Maesil-cheong
1595:
1594:
1593:
1590:
1588:
1585:
1583:
1580:
1578:
1575:
1573:
1570:
1569:
1567:
1565:
1561:
1558:
1554:
1548:
1545:
1543:
1540:
1538:
1535:
1533:
1530:
1528:
1525:
1523:
1520:
1518:
1515:
1513:
1510:
1508:
1505:
1503:
1500:
1499:
1497:
1493:
1487:
1484:
1482:
1479:
1475:
1472:
1470:
1467:
1465:
1462:
1460:
1457:
1456:
1455:
1452:
1448:
1445:
1443:
1440:
1438:
1435:
1433:
1430:
1429:
1428:
1425:
1424:
1422:
1418:
1414:
1409:
1404:
1397:
1392:
1390:
1385:
1383:
1378:
1377:
1374:
1368:
1365:
1364:
1360:
1355:
1354:
1350:
1343:
1339:
1335:
1331:
1330:
1325:
1320:
1317:
1312:
1308:
1302:
1299:
1286:
1282:
1276:
1273:
1268:
1264:
1260:
1258:0-471-95343-1
1254:
1250:
1249:
1241:
1238:
1231:
1227:
1226:Sugar alcohol
1224:
1222:
1219:
1217:
1214:
1212:
1209:
1208:
1204:
1198:
1195:
1193:
1190:
1188:
1187:ascorbic acid
1185:
1184:
1182:
1178:
1175:
1174:
1172:
1168:
1166:
1162:
1160:
1157:
1155:
1152:
1150:
1149:galactosamine
1147:
1146:
1144:
1141:
1140:
1139:
1133:
1118:
1113:
1100:
1095:
1093:
1085:
1081:
1071:
1063:
1061:
1059:
1055:
1050:
1045:
1037:
1029:
1015:
1011:
1009:
1005:
1001:
1000:glucopyranose
998:ring, called
993:
992:glucofuranose
989:
985:
981:
977:
973:
968:
966:
962:
958:
954:
950:
937:
935:
933:
911:
884:
836:
832:
830:
820:
798:
794:
786:
784:
782:
778:
773:
768:
766:
762:
756:
743:
739:
736:
732:
727:
725:
717:
709:
704:
702:
698:
694:
690:
689:stereoisomers
686:
678:
676:
656:
653:
651:
647:
643:
639:
635:
631:
626:
624:
619:
616:
610:
603:
597:
593:
589:
583:
577:
572:
568:
564:
560:
552:
550:
548:
544:
543:sedoheptulose
540:
536:
532:
528:
524:
519:
517:
513:
509:
505:
501:
497:
493:
489:
484:
475:
471:
465:
457:
455:
453:
449:
445:
441:
436:
434:
430:
426:
422:
418:
413:
406:-glucose and
399:
395:
391:
387:
383:
379:
375:
371:
370:disaccharides
367:
363:
359:
354:
351:
342:
338:
334:
330:
326:
321:
319:
318:carbohydrates
315:
311:
307:
306:simple sugars
303:
302:
297:
296:
292:
288:
278:
275:
260:
250:
246:
242:
236:
235:
232:reads like a
230:This article
228:
219:
218:
209:
199:
195:
189:
184:
175:
174:
165:
162:
154:
143:
140:
136:
133:
129:
126:
122:
119:
115:
112: –
111:
107:
106:Find sources:
100:
96:
90:
89:
84:This article
82:
78:
73:
72:
67:
65:
58:
57:
52:
51:
46:
41:
32:
31:
19:
3159:
3148:
3130:
3062:Maltodextrin
2943:Isomaltulose
2734:Deoxy sugars
2670:Ketotetrose
2582:
2573:Mutarotation
2436:
2286:Sugar people
2274:Sugar packet
2198:Molasses Act
2173:Blackbirding
2066:Illovo Sugar
2061:South Africa
2014:Wilmar Sugar
1809:Butterscotch
1804:Barley sugar
1709:
1624:Golden syrup
1602:Mogwa-cheong
1454:Disaccharide
1426:
1327:
1319:
1310:
1301:
1289:. Retrieved
1284:
1275:
1247:
1240:
1164:
1143:Amino sugars
1137:
1067:
1058:mutarotation
1046:
1042:
969:
946:
912:
885:
852:
829:levorotatory
795:of linearly
790:
780:
776:
771:
769:
757:
744:
740:
728:
723:
705:
682:
657:
654:
633:
629:
627:
622:
620:
614:
608:
601:
595:
591:
587:
581:
575:
556:
520:
491:
487:
482:
467:
437:
414:
360:(dextrose),
355:
349:
322:
305:
299:
293:
286:
285:
270:
254:
231:
203:
192:Please help
187:
157:
148:
138:
131:
124:
117:
105:
93:Please help
88:verification
85:
61:
54:
48:
47:Please help
44:
3220:Xanthan gum
3208:Amylopectin
3080:Beta-glucan
2991:Maltotriose
2806:Ketohexoses
2759:Aldohexoses
2739:Deoxyribose
2674:Erythrulose
2632:Ketotriose
2622:Aldotriose
2432:John Yudkin
2342:Fruit syrup
2259:Sugar shack
2249:Added sugar
2188:Holing cane
2046:Philippines
1946:Casa-grande
1860:Other forms
1836:Sugar glass
1799:Sugar candy
1739:Gula melaka
1719:Candi sugar
1698:Solid forms
1689:Yacón syrup
1679:Table syrup
1654:Maple syrup
1607:Yuja-cheong
1577:Agave syrup
1512:Agave syrup
1481:Added sugar
1159:sialic acid
1154:glucosamine
1134:Derivatives
1084:cyclohexane
1049:stereogenic
940:Cyclisation
671:(C=O)(CHOH)
579:(C=O)(CHOH)
470:deoxyribose
433:aldohexoses
412:-fructose.
398:table sugar
341:sweet taste
337:crystalline
320:are built.
243:to make it
3257:Categories
2996:Melezitose
2938:Isomaltose
2933:Cellobiose
2599:Aldodiose
2470:Production
2347:Date honey
2332:Cane knife
2269:Sugar nips
1958:Sugar bush
1941:Plantation
1929:Production
1824:Rock candy
1789:Preserving
1669:Pine honey
1614:Corn syrup
1502:Sugar beet
1351:References
1221:Sugar acid
996:6-membered
961:hemiacetal
883:- prefix.
750:(CO)(CHOH)
701:handedness
565:, and one
462:See also:
444:glycolysis
440:metabolism
298:: single,
257:April 2020
121:newspapers
50:improve it
3150:Galactose
3105:Cellulose
3095:Sizofiran
3019:Stachyose
3001:Raffinose
2968:Trehalose
2953:Lactulose
2774:Galactose
2697:Arabinose
2659:Erythrose
2511:Types of
2406:Sweetness
2401:Sweetener
2291:Sugar tit
2279:Sucrology
2254:Crop Over
2213:Sugar Act
2056:Sri Lanka
2041:Mauritius
2026:Caribbean
1999:Australia
1841:Sugarloaf
1759:Muscovado
1711:Peen tong
1649:Kuromitsu
1507:Sugarcane
1474:Trehalose
1437:Galactose
1420:Chemistry
1145:such as:
976:pyranoses
972:furanoses
965:hemiketal
585:H, where
423:group is
390:cellulose
388:(such as
372:(such as
366:galactose
325:colorless
198:talk page
151:July 2009
56:talk page
3242:Category
3171:Glycogen
3154:Galactan
3132:Fructose
3117:Chitosan
3090:Lentinan
3039:Acarbose
2973:Turanose
2917:Multiple
2858:Heptoses
2846:Rhamnose
2841:Fuculose
2826:Tagatose
2811:Fructose
2727:Xylulose
2722:Ribulose
2686:Pentoses
2648:Tetroses
2551:Geometry
2542:Pyranose
2537:Furanose
2460:Category
2420:Research
2264:Sugaring
2078:Tanzania
1953:Refinery
1921:Industry
1846:Wasanbon
1784:Powdered
1724:Chancaca
1664:Molasses
1556:Products
1532:Honeydew
1432:Fructose
1291:10 March
1267:30894482
1205:See also
1192:mannitol
1023:-glucose
1008:heptoses
849:-glucose
642:aldehyde
567:hydroxyl
559:carbonyl
446:and the
429:isomeric
421:hydroxyl
362:fructose
314:monomers
234:textbook
3213:Amylose
3161:Glucose
3136:Fructan
3126:Dextran
3122:Dextrin
3100:Zymosan
2963:Sucrose
2958:Maltose
2948:Lactose
2897:Nonoses
2892:Octoses
2885:Above 7
2821:Sorbose
2816:Psicose
2794:Mannose
2779:Glucose
2769:Altrose
2751:Hexoses
2664:Threose
2615:Trioses
2520:General
2411:Vinasse
2322:Bagasse
2310:Related
2242:Culture
2155:History
1968:Engenho
1936:Boilery
1902:Tuzemák
1867:Caramel
1794:Sucanat
1744:Jaggery
1734:Gelling
1684:Treacle
1659:Mizuame
1522:Coconut
1495:Sources
1469:Sucrose
1464:Maltose
1459:Lactose
1442:Glucose
1054:anomers
1004:oxepane
988:glucose
765:threose
746:H(CHOH)
535:ketoses
516:heptose
508:pentose
504:tetrose
396:). The
382:maltose
378:lactose
374:sucrose
358:glucose
333:soluble
301:sacchar
245:neutral
239:Please
135:scholar
3203:Starch
3198:Pectin
3193:Mannan
3188:Lignin
3165:Glucan
3142:Inulin
3110:Chitin
2836:Fucose
2799:Talose
2784:Gulose
2764:Allose
2712:Xylose
2707:Ribose
2702:Lyxose
2592:Dioses
2568:Epimer
2558:Anomer
2532:Ketose
2527:Aldose
2441:(1972)
2369:Nectar
2357:Jallab
2141:Hawaii
2083:Uganda
2051:Rwanda
1829:Toffee
1774:Panela
1592:Cheong
1564:Syrups
1447:Xylose
1265:
1255:
957:oxygen
949:cyclic
932:system
919:- and
892:- and
859:- and
843:- and
805:- and
697:chiral
650:ketone
646:aldose
638:formyl
590:+ 1 +
561:(C=O)
523:hexose
512:hexose
500:triose
496:carbon
425:chiral
417:carbon
394:starch
384:) and
335:, and
289:(from
137:
130:
123:
116:
108:
3058:(IMO)
3052:(GOS)
3046:(FOS)
3028:Other
2789:Idose
2352:Grape
2036:India
2031:Kenya
1978:Zafra
1973:Batey
1851:White
1814:Candy
1749:Misri
1705:Brown
1639:Honey
1537:Maple
1517:Birch
1403:Sugar
1324:IUPAC
1232:Notes
984:pyran
980:furan
571:atoms
514:(6),
510:(5),
506:(4),
502:(3),
476:: (CH
415:Each
329:water
310:sugar
295:monos
291:Greek
142:JSTOR
128:books
2136:Fiji
2021:Cuba
1819:Hard
1547:Malt
1542:Palm
1527:Date
1293:2017
1263:OCLC
1253:ISBN
982:and
974:and
853:The
729:The
541:and
529:and
392:and
380:and
114:news
2009:CSR
1882:Rum
1764:Nib
1338:doi
1336:".
963:or
929:D/L
714:H (
632:or
531:DNA
527:RNA
494:of
97:by
3259::
3163:/
3152:/
3134:/
3124:/
1326:,
1283:.
1261:.
1122:β-
1104:α-
1010:.
934:.
767:.
618:.
594:=
537:,
480:O)
376:,
347:O)
327:,
59:.
2504:e
2497:t
2490:v
1395:e
1388:t
1381:v
1340::
1295:.
1269:.
1165:N
1125:D
1107:D
1089:D
1075:D
1052:(
1020:D
922:L
916:D
907:L
901:D
895:L
889:D
880:L
874:D
868:D
862:L
856:D
846:L
840:D
824:L
814:D
808:L
802:D
781:n
777:n
772:n
752:2
748:2
724:c
720:2
712:2
673:2
669:2
665:3
661:4
634:m
630:n
623:x
615:x
612:O
609:x
607:2
605:H
602:x
596:x
592:m
588:n
582:m
576:n
492:x
488:x
483:x
478:2
409:D
403:D
350:x
345:2
331:-
277:)
271:(
259:)
255:(
251:.
237:.
208:)
204:(
200:.
190:.
164:)
158:(
153:)
149:(
139:·
132:·
125:·
118:·
91:.
66:)
62:(
20:)
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