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.

引用

页码：1726 / 1731

页数：6

共 36 条

[31] THE CONFORMATIONAL PROPERTIES OF THE GANGLIOSIDES GM2 AND GM1 BASED ON H-1 AND C-13 NUCLEAR MAGNETIC-RESONANCE STUDIES [J].