A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art

被引：102

作者：

Bohe, Luis ^{[1
]}

Crich, David ^{[2
]}

机构：

[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France

[2] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

来源：

CARBOHYDRATE RESEARCH | 2015年 / 403卷

关键词：

Oxocarbenium ions; Counter ions; Hydrogen bonding; Kinetics; PROTECTING GROUPS; OLIGOSACCHARIDE SYNTHESIS; BETA-ARABINOFURANOSIDES; GLYCOSIDATION REACTIONS; BOND FORMATION; TWIST-BOAT; DONORS; REACTIVITY; CHEMISTRY; STEREOSELECTIVITY;

D O I：

10.1016/j.carres.2014.06.020

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：

An overview of recent advances in glycosylation with particular emphasis on mechanism is presented. The mounting evidence for both the existence of glycosyl oxocarbenium ions as fleeting intermediates in some reactions, and the crucial role of the associated counterion in others is discussed. The extremes of the S(N)1 and S(N)2 manifolds for the glycosylation reaction are bridged by a continuum of mechanisms in which it appears likely that most examples are located. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：48 / 59

页数：12

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