The synthesis and structure of the derivatives of 2-deoxy-2-hydroxyimino-D-lyxo-hexopyranosyl-L-cysteine and -thiophenol

被引：6
|
作者：
Liberek, B
Konitz, A
Frankowski, R
Smiatacz, Z
机构：
[1] Univ Gdansk, Fac Chem, PL-80952 Gdansk, Poland
[2] Gdansk Tech Univ, Dept Inorgan Chem, PL-80952 Gdansk, Poland
来源：
CARBOHYDRATE RESEARCH | 2000年 / 326卷 / 02期
关键词：
thioglycosides; L-cysteine and thiophenol derivatives; 2-deoxy-2-hydroxyimino sugars; conformation and configuration; X-ray diffraction;
D O I：
10.1016/S0008-6215(00)00035-5
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
3,4,6-Tri-O-acetyl-2-deoxy-2-hydroxyimino-beta and -alpha-D-lyxo-hexopyranosides of thiophenol (3, 4) and the methyl ester of N-benzoyl-L-cysteine have been synthesised by condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-alpha-D- galactopyranosyl chloride with thiophenol and the L-cysteine derivative, respectively. The conformation of the sugar residue and configuration of the anomeric centre as well as of the hydroxyimino group were established on the basis of the H-1 NMR (DQF-COSY, ROESY, TOCSY) spectrometric techniques and polarimetric data. Additionally, the structure of S-[3,4,6-tri-O-acetyl-2-deoxy-2-(Z)-hydroxyimino-beta-D-lyxo-hexopyranosyl]-thiophenol (3) was supported by X-ray diffraction data. (C) 2000 Elsevier Science Ltd. All rights reserved.
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页码：151 / 158
页数：8
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