Glycosidic bond formation in aqueous solution: On the oxocarbenium intermediate

被引：29
|
作者：
Stubbs, JM [1 ]
Marx, D [1 ]
机构：
[1] Ruhr Univ Bochum, Lehrstuhl Theoret Chem, D-44780 Bochum, Germany
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 36期
关键词：
D O I：
10.1021/ja035600n
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The mechanism of specific acid-catalyzed glycosidic bond formation between methanol and alpha-D-glucopyranoside in aqueous solution at 300 K was studied using Car-Parrinello molecular dynamics. The reaction was found to proceed through a non-solvent equilibrated oxocarbenium cation intermediate characterized by the loss of a hydrogen-bonding interaction between the ring oxygen and solvating water. The mechanism, which was found to be D-N*A(N) in nature, is discussed in detail.
引用
收藏
页码：10960 / 10962
页数：3
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