PREFERRED CONFORMATION ABOUT THE C5-C6 BOND OF N-ACETYLNEURAMINYL(2-6)-D-GALACTOPYRANOSIDES AND N-ACETYLNEURAMINYL(2-6)-D-GLUCOPYRANOSIDES IN SOLUTION

被引：37

作者：

OHRUI, H

NISHIDA, Y

ITOH, H

MEGURO, H

机构：

[1] Department of Food Chemistry, Faculty of Agriculture, Tohoku University, Aoba-Ku, Sendai 981

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 05期

关键词：

D O I：

10.1021/jo00005a015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoselective deuteration and H-1 NMR spectroscopy were applied in a conformational study of the C5-C6 bond in four stereoisomeric methyl N-acetylneuraminyl(2-6)-beta-D-hexopyranosides [NeuNAc-alpha(2-6)Gal, NeuNAc-beta-(2-6)Gal, NeuNAc-alpha-(2-6)Glc, and NeuNAc-beta-(2-6)Glc]. In aqueous solution, NeuNAc-alpha-(2-6)Gal prefers a gt conformer (gg:gt:tg = ca. 20:60:20), NeuNAc(2-6)Glc isomers prefer a gg (gg:gt:tg = ca. 60:40:0), and NeuNAc-beta-(2-6)Gal exists equally in the three conformers.

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页码：1726 / 1731

页数：6

相关论文

共 36 条

[1] STRUCTURAL AND CONFORMATIONAL-ANALYSIS OF SIALYLOLIGOSACCHARIDES USING C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY [J].

BERMAN, E .

BIOCHEMISTRY, 1984, 23 (16) :3754-3759

[2]

BOCK K, 1982, CAN J CHEM, V60, P44

[3] CONFORMATIONAL-ANALYSIS OF THE SIALYL-ALPHA-(2-]3/6)N-ACETYLLACTOSAMINE STRUCTURAL ELEMENT OCCURRING IN GLYCOPROTEINS, BY TWO-DIMENSIONAL NOE H-1-NMR SPECTROSCOPY IN COMBINATION WITH ENERGY CALCULATIONS BY HARD-SPHERE EXO-ANOMERIC AND MOLECULAR MECHANICS FORCE-FIELD WITH HYDROGEN-BONDING POTENTIAL [J].

BREG, J ;

KROONBATENBURG, LMJ ;

STRECKER, G ;

MONTREUIL, J ;

VLIEGENTHART, JFG .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1989, 178 (03) :727-739

[4] ON THE SIDE-CHAIN CONFORMATION OF N-ACETYLNEURAMINIC ACID AND ITS EPIMERS AT C-7, C-8, AND C-7,8 [J].

CHRISTIAN, R ;

SCHULZ, G ;

BRANDSTETTER, HH ;

ZBIRAL, E .

CARBOHYDRATE RESEARCH, 1987, 162 (01) :1-11

[5]

DABROWSKI U, 1979, TETRAHEDRON LETT, P4637

[6]

FURUHATA K, 1986, CHEM PHARM BULL, V34, P2725

[7]

FURUHATA K, 1984, YUKI GOUSEI KYOUKAIS, V42, P536

[8] THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION [J].

HAASNOOT, CAG ;

DELEEUW, FAAM ;

ALTONA, C .

TETRAHEDRON, 1980, 36 (19) :2783-2792

[9] TUMOR-ASSOCIATED CARBOHYDRATE ANTIGENS [J].

HAKOMORI, S .

ANNUAL REVIEW OF IMMUNOLOGY, 1984, 2 :103-126

[10] CHIRAL DEUTERATION AT C-6 OF 1,6-ANHYDROHEXOSE DERIVATIVES [J].

HORI, H ;

NAKAJIMA, T ;

NISHIDA, Y ;

OHRUI, H ;

MEGURO, H .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1986, 5 (04) :585-600

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