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合成受体类似物：通过核磁共振和计算方法确定的4-O-α-D-吡喃半乳糖基-β-D-吡喃半乳糖苷甲酯（β-D-半乳糖二糖苷甲酯）及相关衍生物的构象

Synthetic receptor analogues: the conformation of methyl 4-O-alpha-D-galactopyranosyl-beta-D-galactopyranoside (methyl beta-D-galabioside) and related derivatives, determined by n.m.r. and computational methods.

作者信息

Bock K, Frejd T, Kihlberg J, Magnusson G

机构信息

Department of Organic Chemistry, Technical University of Denmark, Lyngby.

出版信息

Carbohydr Res. 1988 May 15;176(2):253-70. doi: 10.1016/0008-6215(88)80137-x.

DOI:10.1016/0008-6215(88)80137-x
PMID:3416320
Abstract

The conformations of galabiose and its methyl and ethyl beta-glycosides as well as the 3-deoxy, 3-O-methyl, 3-deoxy-3-C-methyl, 3-deoxy-3-C-ethyl, and 6-deoxy analogues were investigated by n.m.r. (1H, 13C, n.O.e.) and computational (HSEA) methods. A good correlation was found between the computational data and the n.m.r. data for aqueous solutions. The conformations in aqueous solution were similar, whereas crystalline galabiose or methyl beta-D-galabioside in solution in methyl sulfoxide adopted different conformations that showed intramolecular hydrogen bonds (O-5'. . . O-3 and O-2'. . . O-6, respectively).

摘要

通过核磁共振（¹H、¹³C、核Overhauser效应）和计算（HSEA）方法研究了半乳糖二糖及其甲基和乙基β-糖苷以及3-脱氧、3-O-甲基、3-脱氧-3-C-甲基、3-脱氧-3-C-乙基和6-脱氧类似物的构象。发现计算数据与水溶液的核磁共振数据之间具有良好的相关性。水溶液中的构象相似，而结晶半乳糖二糖或甲基亚砜溶液中的甲基β-D-半乳糖二糖苷采用不同的构象，分别显示出分子内氢键（O-5'...O-3和O-2'...O-6）。

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1
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