Chemistry of vinyl sulfones.: Approach to novel conformationally restricted analogues of glutamic acid

被引：17

作者：

Díez, D

García, P

Marcos, IS

Garrido, NM

Basabe, P

Broughton, HB

Urones, JG

机构：

[1] Univ Salamanca, Fac Ciencias Quim, Dept Quim Organ, E-37008 Salamanca, Spain

[2] Lilly SA, Madrid 28108, Spain

来源：

TETRAHEDRON | 2005年 / 61卷 / 03期

关键词：

D O I：

10.1016/j.tet.2004.10.072

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A totally different approach to conformationally restricted glutamic acid analogues is described, in which one of the acid functions is replaced by a cyclopropanol. The reactivity of cyclopropanol vinyl sulfones toward addition of lithiated Schollkopf bislactim ether provides a facile synthesis of a-amino acid diastereoisomers. Conformational analysis of these analogues, incorporating solvation effects, and docking to a glutamate receptor model, are used to show the relevance of the conformational restrictions employed. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：699 / 707

页数：9

共 24 条

[11]

Halgren TA, 1996, J COMPUT CHEM, V17, P490, DOI [10.1002/(SICI)1096-987X(199604)17:5/6<490::AID-JCC1>3.0.CO

[12]

2-P, 10.1002/(SICI)1096-987X(199604)17:5/6<616::AID-JCC5>3.0.CO

[13]

2-X]

[14] Conformationally constrained 7-azabicyclo[2.2.1]heptane amino acids. Synthesis of a glutamic acid analogue [J].