Density functional theory study, of the stereoselectivity in small peptide-catalyzed intermolecular aldol reactions

被引：13

作者：

Hammar, Peter ^{[2
]}

Cordova, Armando ^{[1
]}

Himo, Fahmi ^{[2
]}

机构：

[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden

[2] Royal Inst Technol, Dept Theoret Chem, Sch Biotechnol, SE-10691 Stockholm, Sweden

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 13期

关键词：

D O I：

10.1016/j.tetasy.2008.06.014

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The origins of the stereoselection of the dipeptide-catalyzed intermolecular aldol reaction are explored by means of hybrid density functional theory. Transition states were located for the (S)-ala-(S)-ala-catalyzed aldol reaction with cyclohexanone as the donor and benzaldehyde as the acceptor. The calculations reproduce the experimental trends very satisfactorily. It is demonstrated that the main Source of stereoselectivity is the interaction of the N-terminal amino acid side chain of the dipeptide with the cyclohexene ring. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：1617 / 1621

页数：5

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