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Amylose

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519:, or low-molecular-weight sugars can reduce the loss in stability. The ability to bind water can add substance to food, possibly serving as a fat replacement. For example, amylose is responsible for causing white sauce to thicken, but, upon cooling, the solid and the water will partly separate. Amylose is known for its good film-forming properties, useful in food packaging. Excellent film-forming behavior of amylose was studied already in 1950s. Amylose films are better for both barrier properties and mechanical properties when compared to the amylopectin films. 175: 125: 252: 2129: 453:(which has short, highly branched chains), high-amylose starch is more resistant to digestion. Unlike amylopectin, amylose is insoluble in water. It also reduces the crystallinity of amylopectin and how easily water can infiltrate the starch. The higher the amylose content, the less expansion potential and the lower the gel strength for the same starch concentration. This can be countered partially by increasing the granule size. 24: 303: 257: 256: 440:
Fiber X-ray diffraction analysis coupled with computer-based structure refinement has found A-, B-, and C- polymorphs of amylose. Each form corresponds to either the A-, the B-, or the C- starch forms. A- and B- structures have different helical crystal structures and water contents, whereas the C-
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Researchers have identified the Granule Bound Starch Synthase (GBSS) as the enzyme that specifically elongates amylose during starch biosynthesis in plants. The waxy locus in maize encodes for the GBSS protein. Mutants lacking the GBSS protein produce starch containing only
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Amylose is made up of α(1→4) bound glucose molecules. The carbon atoms on glucose are numbered, starting at the aldehyde (C=O) carbon, so, in amylose, the 1-carbon on one glucose molecule is linked to the 4-carbon on the next glucose molecule (α(1→4) bonds). The
465:; however, because of its helical structure, it takes up less space than amylopectin. As a result, it is the preferred starch for storage in plants. It makes up about 30% of the stored starch in plants, though the percentage varies by species and variety. 581:. In Arabidopsis leaves, another gene, encoding the Protein Targeting to STarch (PTST) protein, is required in addition to GBSS for amylose synthesis. Mutants lacking either protein produce starch without amylose. Genetically modified potato cultivar 855: 860:
A survey of 22 popular organic chemistry textbooks showed that only four correctly stated that of the two components of starch, amylopectin is the water-soluble, and amylose is the water-insoluble.
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Juliano, B. O.; Perez, C. M.; Komindr, S.; Banphotkasem, S. (December 1989). "Properties of Thai cooked rice and noodles differing in glycemic index in noninsulin-dependent diabetics".
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Zhong, Fang; Yokoyama, Wallace; Wang, Qian; Shoemaker, Charles F (2006). "Rice Starch, Amylopectin, and Amylose: Molecular Weight and Solubility in Dimethyl Sulfoxide-Based Solvents".
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structure, making it possible for hydrogen bonds to form between the oxygen atoms bound at the 2-carbon of one glucose molecule and the 3-carbon of the next glucose molecule.
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Rindlav-Westling, A˚sa; Stading, Mats; Hermansson, Anne-Marie; Gatenholm, Paul (July 1998). "Structure, mechanical and barrier properties of amylose and amylopectin films".
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Amylose is also an important thickener, water binder, emulsion stabilizer, and gelling agent in industrial and food-based contexts. Loose helical amylose chains have a
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There are three main forms of amylose chains can take. It can exist in a disordered amorphous conformation or two different helical forms. It can bind with itself in a
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for starch. If starch is mixed with a small amount of yellow iodine solution, a blue-black color will be observed. The intensity of the color can be tested with a
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Myllärinen, Päivi; Partanen, Riitta; Seppälä, Jukka; Forssell, Pirkko (December 2002). "Effect of glycerol on behaviour of amylose and amylopectin films".
1290:"PROTEIN TARGETING TO STARCH is Required for Localising GRANULE-BOUND STARCH SYNTHASE to Starch Granules and for Normal Amylose Synthesis in Arabidopsis" 316: 804:
Birt DF, Boylston T, Hendrich S, Jane JL, Hollis J, Li L, McClelland J, Moore S, Phillips GJ, Rowling M, Schalinske K, Scott MP, Whitley EM (2013).
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of amylose is pictured at right. The number of repeated glucose subunits (n) is usually in the range of 300 to 3000, but can be many thousands.
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Cohen, R.; Orlova, Y.; Kovalev, M.; Ungar, Y.; Shimoni, E. (2008). "Structural and Functional Properties of Amylose Complexes with Genistein".
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Chung, Hyun-Jung; Liu, Qiang (2009). "Impact of molecular structure of amylopectin and amylose on amylose chain association during cooling".
495:. The one problem with this is that, when it crystallizes or associates, it can lose some stability, often releasing water in the process ( 1153: 433:, but for the most part bound glucose ring oxygens lie on one side of the structure. The α(1→4) structure promotes the formation of a 273: 631:
Green, Mark M.; Blankenhorn, Glenn; Hart, Harold (November 1975). "Which Starch Fraction is Water-Soluble, Amylose or Amylopectin?".
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Wolff, Ivan A.; Davis, H. A.; Cluskey, J. E.; Gundrum, L. J.; Rist, Carl E. (April 1951). "Preparation of Films from Amylose".
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Green, Mark M; Blankenhorn, Glenn; Hart, Harold (1975). "Which starch fraction is water-soluble, amylose or amylopectin?".
499:). When amylose concentration is increased, gel stickiness decreases but firmness increases. When other things, including 752: 441:
structure is a mixture of A- and B- unit cells, resulting in an intermediate packing density between the two forms.
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structure, amylose is more resistant to digestion than other starch molecules and is therefore an important form of
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Nelson, David and Michael M. Cox. Principles of Biochemistry. 5th ed. New York: W. H. Freeman and Company , 2008.
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in titrations involving iodine reduction. It is also used in amylose magnetic beads and resin to separate
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Sarko, A; Wu, H.-C. H (1978). "The Crystal Structures of A-, B- and C-Polymorphs of Amylose and Starch".
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Seung, David; Soyk, Sebastian; Coiro, Mario; Maier, Benjamin A; Eicke, Simona; Zeeman, Samuel C (2015).
943:"Physicochemical, thermal and rheological properties of starches isolated from malting barley varieties" 909:"Relationships between thermal, rheological characteristics and swelling power for various starches" 2153: 1453: 170: 1946: 702: 547: 539: 2132: 1940: 1379: 908: 1934: 810: 610: 496: 36: 2073: 881: 640: 141: 66: 8: 1253:
Keeling, Peter L; Myers, Alan M (2010). "Biochemistry and Genetics of Starch Synthesis".
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forms exist as well. These provide an even larger space for the guest molecule to bind.
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Amylose is important in plant energy storage. It is less readily digested than
430: 339: 294: 958: 394:(A or B form), or it can bind with another hydrophobic guest molecule such as 2147: 2068: 1985: 1873: 1764: 1220: 790: 562: 469: 113: 1008: 1952: 1833: 1815: 1463: 1403: 1364: 1325: 1274: 1027: 976: 841: 735: 391: 1228: 1094: 823: 756: 279: 2110: 2098: 1970: 1881: 1629: 1624: 1564: 1371: 574: 535: 531: 516: 508: 500: 484: 473: 462: 450: 407: 1081: 449:
Because the long linear chains of amylose more readily crystallize than
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of amylose, binding with the starch polymer that absorbs certain known
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Wang, Juan; Hu, Pan; Chen, Zichun; Liu, Qiaoquan; Wei, Cunxu (2017).
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Pycia, K; Gałkowska, D; Juszczak, L; Fortuna, T; Witczak, T (2014).
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Except where otherwise noted, data are given for materials in their
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a visualisation with references to the literature is found here
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Amylose A is a parallel double-helix of linear chains of glucose
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Plant Foods for Human Nutrition (Dordrecht, Netherlands)
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interior that can bind to hydrophobic molecules such as
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This linear structure can have some rotation around the
713: 806:"Resistant starch: promise for improving human health" 561:, the less sticky long-grain rice, have a much lower 1248: 1246: 871: 657:... amylose is the water-insoluble starch component. 630: 1287: 1243: 747: 745: 522:In a laboratory setting, it can act as a marker. 2145: 254: 65: 742: 1387: 989: 1255:Annual Review of Food Science and Technology 1252: 797: 418:form, which has six glucose units a turn. V 350:units, bonded to each other through α(1→4) 1401: 1394: 1380: 1345:Journal of Agricultural and Food Chemistry 716:Journal of Agricultural and Food Chemistry 480:, which can be used as sources of energy. 173: 123: 1315: 1305: 1017: 1007: 966: 831: 406:. This is known as the V form and is how 140: 1040: 373: 776: 169: 2146: 1070:Industrial & Engineering Chemistry 947:Journal of Food Science and Technology 589:was developed to not produce amylose. 534:of light. Hence, a common test is the 444: 114: 1375: 1150:"Biochemistry Structure and Function" 983: 906: 507:can be affected, but incorporating κ- 410:binds to amylose in the structure of 354:. It is one of the two components of 85: 13: 1267:10.1146/annurev.food.102308.124214 472:breaks down starch molecules into 250: 14: 2170: 1336: 907:Li, Jeng-Yune; Yeh, An-I (2001). 552: 2128: 2127: 565:, which could be beneficial for 526:molecules fit neatly inside the 301: 22: 1281: 1192: 1167: 1142: 1115: 1088: 1061: 1034: 934: 900: 865: 297:(at 25 °C , 100 kPa). 848: 770: 707: 696: 687: 662: 624: 613:, high amylose potato cultivar 1: 1136:10.1016/S0144-8617(02)00042-5 1109:10.1016/S0144-8617(98)00025-3 1055:10.1016/j.carbpol.2009.03.004 928:10.1016/S0260-8774(00)00236-3 874:Journal of Chemical Education 633:Journal of Chemical Education 617: 1307:10.1371/journal.pbio.1002080 369: 7: 916:Journal of Food Engineering 607:, high amylose maize starch 592: 456: 10: 2175: 996:Frontiers in Plant Science 557:High-amylose varieties of 2123: 1961: 1918: 1900: 1872: 1814: 1807: 1775: 1747: 1640: 1575: 1537: 1504: 1481: 1472: 1441: 1410: 959:10.1007/s13197-014-1531-3 291: 232: 185: 49: 35: 30: 21: 1454:Cyclohexane conformation 791:10.1002/star.19780300302 1947:Isomaltooligosaccharide 1009:10.3389/fpls.2017.00469 548:maltose-binding protein 503:, bind to amylose, the 1941:Galactooligosaccharide 544:starch as an indicator 379: 261: 208:Variable 1935:Fructooligosaccharide 1124:Carbohydrate Polymers 1097:Carbohydrate Polymers 1043:Carbohydrate Polymers 824:10.3945/an.113.004325 811:Advances in Nutrition 611:Russet Burbank potato 468:The digestive enzyme 377: 260: 243:(fire diamond) 1082:10.1021/ie50496a039 886:1975JChEd..52..729G 645:1975JChEd..52..729G 445:Physical properties 223:Solubility in water 18: 1213:10.1007/bf01092074 670:"Resistant starch" 587:BASF Plant Science 493:aromatic compounds 431:phi and psi angles 385:structural formula 380: 324:Infobox references 262: 16: 2141: 2140: 2119: 2118: 1803: 1802: 1357:10.1021/jf051918i 894:10.1021/ed052p729 728:10.1021/jf800255c 722:(11): 4212–4218. 653:10.1021/ed052p729 528:helical structure 404:aromatic compound 345: 332:Chemical compound 330: 329: 154:CompTox Dashboard 43: 2166: 2131: 2130: 1922:oligosaccharides 1902:Tetrasaccharides 1812: 1811: 1527:Dihydroxyacetone 1479: 1478: 1396: 1389: 1382: 1373: 1372: 1368: 1351:(6): 2320–2326. 1330: 1329: 1319: 1309: 1285: 1279: 1278: 1250: 1241: 1240: 1196: 1190: 1189: 1187: 1186: 1177:. Archived from 1171: 1165: 1164: 1162: 1161: 1152:. Archived from 1146: 1140: 1139: 1119: 1113: 1112: 1103:(2–3): 217–224. 1092: 1086: 1085: 1065: 1059: 1058: 1038: 1032: 1031: 1021: 1011: 987: 981: 980: 970: 953:(8): 4797–4807. 938: 932: 931: 913: 904: 898: 897: 869: 863: 862: 852: 846: 845: 835: 801: 795: 794: 774: 768: 767: 765: 764: 755:. Archived from 749: 740: 739: 711: 705: 700: 694: 691: 685: 684: 682: 681: 672:. Archived from 666: 660: 659: 628: 364:resistant starch 352:glycosidic bonds 343: 314: 308: 305: 304: 282: 275: 268: 253: 193:Chemical formula 178: 177: 162: 160: 144: 127: 116: 89: 69: 41: 26: 19: 15: 2174: 2173: 2169: 2168: 2167: 2165: 2164: 2163: 2154:Polysaccharides 2144: 2143: 2142: 2137: 2115: 1976:Oat beta-glucan 1963:Polysaccharides 1957: 1920: 1914: 1896: 1868: 1799: 1793:Neuraminic acid 1771: 1743: 1636: 1571: 1533: 1500: 1474:Monosaccharides 1468: 1437: 1406: 1400: 1339: 1334: 1333: 1300:(2): e1002080. 1286: 1282: 1251: 1244: 1197: 1193: 1184: 1182: 1173: 1172: 1168: 1159: 1157: 1148: 1147: 1143: 1120: 1116: 1093: 1089: 1066: 1062: 1039: 1035: 988: 984: 939: 935: 911: 905: 901: 870: 866: 854: 853: 849: 802: 798: 779:Starch - Stärke 775: 771: 762: 760: 751: 750: 743: 712: 708: 701: 697: 692: 688: 679: 677: 668: 667: 663: 629: 625: 620: 595: 555: 459: 447: 425: 421: 417: 372: 333: 326: 321: 320: 319:  ?) 310: 306: 302: 298: 287: 286: 285: 284: 277: 270: 263: 259: 251: 225: 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Retrieved 674:the original 664: 656: 636: 632: 626: 571: 556: 521: 482: 467: 460: 448: 439: 428: 392:double helix 389: 381: 335: 334: 239: 50:Identifiers 2111:Xanthan gum 2099:Amylopectin 1971:Beta-glucan 1882:Maltotriose 1697:Ketohexoses 1650:Aldohexoses 1630:Deoxyribose 1565:Erythrulose 1523:Ketotriose 1513:Aldotriose 1261:: 271–303. 880:(11): 729. 639:(11): 729. 575:amylopectin 540:colorimeter 536:iodine test 532:wavelengths 517:xanthan gum 509:carrageenan 501:amylopectin 485:hydrophobic 474:maltotriose 463:amylopectin 451:amylopectin 408:amylopectin 213:Appearance 186:Properties 121:100.029.702 87:CHEBI:28102 2148:Categories 1887:Melezitose 1829:Isomaltose 1824:Cellobiose 1490:Aldodiose 1185:2010-05-25 1160:2010-05-25 763:2010-05-25 680:2010-07-02 618:References 605:Amylomaize 400:fatty acid 342:made of α- 228:Insoluble 204:Molar mass 142:7TDQ74Y18L 98:ChemSpider 57:CAS Number 37:IUPAC name 2041:Galactose 1996:Cellulose 1986:Sizofiran 1910:Stachyose 1892:Raffinose 1859:Trehalose 1844:Lactulose 1665:Galactose 1588:Arabinose 1550:Erythrose 1402:Types of 1237:189939655 1221:0921-9668 579:waxy corn 567:diabetics 505:viscosity 497:syneresis 470:α-amylase 370:Structure 67:9005-82-7 2133:Category 2062:Glycogen 2045:Galactan 2023:Fructose 2008:Chitosan 1981:Lentinan 1930:Acarbose 1864:Turanose 1808:Multiple 1749:Heptoses 1737:Rhamnose 1732:Fuculose 1717:Tagatose 1702:Fructose 1618:Xylulose 1613:Ribulose 1577:Pentoses 1539:Tetroses 1442:Geometry 1433:Pyranose 1428:Furanose 1365:16536614 1326:25710501 1275:22129338 1028:28421099 977:26243900 842:24228189 753:"Starch" 736:18489110 593:See also 513:alginate 457:Function 402:, or an 240:NFPA 704 233:Hazards 40:(1→4)-α- 17:Amylose 2104:Amylose 2052:Glucose 2027:Fructan 2017:Dextran 2013:Dextrin 1991:Zymosan 1854:Sucrose 1849:Maltose 1839:Lactose 1788:Nonoses 1783:Octoses 1776:Above 7 1712:Sorbose 1707:Psicose 1685:Mannose 1670:Glucose 1660:Altrose 1642:Hexoses 1555:Threose 1506:Trioses 1411:General 1317:4339375 1229:2631091 1019:5379859 1002:: 469. 968:4519444 882:Bibcode 833:3823506 641:Bibcode 599:Amflora 583:Amflora 478:maltose 360:helical 348:glucose 336:Amylose 317:what is 315: ( 2159:Starch 2094:Starch 2089:Pectin 2084:Mannan 2079:Lignin 2056:Glucan 2033:Inulin 2001:Chitin 1727:Fucose 1690:Talose 1675:Gulose 1655:Allose 1603:Xylose 1598:Ribose 1593:Lyxose 1483:Dioses 1459:Epimer 1449:Anomer 1423:Ketose 1418:Aldose 1363:  1324:  1314:  1273:  1235:  1227:  1219:  1026:  1016:  975:  965:  840:  830:  734:  524:Iodine 489:lipids 412:starch 396:iodine 356:starch 312:verify 309:  31:Names 1949:(IMO) 1943:(GOS) 1937:(FOS) 1919:Other 1680:Idose 1233:S2CID 912:(PDF) 435:helix 338:is a 78:ChEBI 1361:PMID 1322:PMID 1271:PMID 1225:PMID 1217:ISSN 1024:PMID 973:PMID 838:PMID 732:PMID 559:rice 491:and 476:and 398:, a 133:UNII 105:None 1353:doi 1312:PMC 1302:doi 1263:doi 1209:doi 1132:doi 1105:doi 1078:doi 1051:doi 1014:PMC 1004:doi 963:PMC 955:doi 924:doi 890:doi 828:PMC 820:doi 787:doi 724:doi 649:doi 585:by 159:EPA 2150:: 2054:/ 2043:/ 2025:/ 2015:/ 1359:. 1349:54 1347:. 1320:. 1310:. 1298:13 1296:. 1292:. 1269:. 1257:. 1245:^ 1231:. 1223:. 1215:. 1205:39 1203:. 1128:50 1126:. 1101:36 1099:. 1074:43 1072:. 1047:77 1045:. 1022:. 1012:. 998:. 994:. 971:. 961:. 951:52 949:. 945:. 920:50 918:. 914:. 888:. 878:52 876:. 858:. 836:. 826:. 814:. 808:. 783:30 781:. 744:^ 730:. 720:56 718:. 655:. 647:. 637:52 635:. 569:. 515:, 511:, 366:. 1395:e 1388:t 1381:v 1367:. 1355:: 1328:. 1304:: 1277:. 1265:: 1259:1 1239:. 1211:: 1188:. 1163:. 1138:. 1134:: 1111:. 1107:: 1084:. 1080:: 1057:. 1053:: 1030:. 1006:: 1000:8 979:. 957:: 930:. 926:: 896:. 892:: 884:: 844:. 822:: 816:4 793:. 789:: 766:. 738:. 726:: 683:. 651:: 643:: 424:7 420:8 416:6 346:- 344:D 307:N 281:0 274:1 267:1 161:) 157:( 42:D

Index


IUPAC name
CAS Number
9005-82-7
ChEBI
CHEBI:28102
ChemSpider
ECHA InfoCard
100.029.702
Edit this at Wikidata
UNII
7TDQ74Y18L
CompTox Dashboard
DTXSID8093813
Edit this at Wikidata
Chemical formula
Molar mass
Solubility in water
NFPA 704
1
1
0
standard state
verify
what is
Infobox references
polysaccharide
glucose
glycosidic bonds
starch

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