Stereospecific synthesis of methyl 2-amino-2-deoxy-(6S)-deuterio-α,β-D-glucopyranoside and methyl 2,6-diamino-2,6-dideoxy-(6R)deuterio-α,β-D-glucopyranoside: Side chain conformations of the 2amino-2-deoxy and 2,6-diamino-2,6-dideoxyglucopyranosides

被引：11

作者：

Kato, Takayuki ^{[1
]}

Vasella, Andrea ^{[2
]}

Crich, David ^{[1
]}

机构：

[1] Wayne State Univ, Dept Chem, 5101 Cass Ave, Detroit, MI 48202 USA

[2] Swiss Fed Inst Technol, Organ Chem Lab, CH-8093 Zurich, Switzerland

来源：

CARBOHYDRATE RESEARCH | 2017年 / 448卷

关键词：

Side chain conformation; Deuterium labelling; Conformational analysis; Aminosugars; PREFERRED ROTAMERS; C5-C6; BOND; DERIVATIVES; NMR; ASSIGNMENT; INHIBITORS; H-1-NMR; HEXOSES; SUGARS;

D O I：

10.1016/j.carres.2017.05.015

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：

The stereospecifically labeled 6-monodeuterio methyl 2,6-diamino-2,6-dideoxy-alpha- and beta- o-glucopyranosides were synthesized with a view to determining their side chain conformations. NMR studies in D2O at pH 5 and pH 11 reveal both anomers to adopt very predominantly the gt conformation consistent with the gauche conformation of 2-aminoethanol and its acetate salt. In contrast, as also revealed with the help of stereospecifically-labelled monodeuterio isotopomers, the methyl 2-amino-2-deoxy-alpha- and beta- D-glucopyranosides are an approximately 1:1 mixture of gg and gt conformers as is found in glucopyranose itself. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：10 / 17

页数：8

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