Cyclopropane analogue of valine:: influence of side chain orientation on peptide folding

被引：16

作者：

Jiménez, AI

Marraud, M

Cativiela, C

机构：

[1] Univ Zaragoza, CSIC, ICMA, Dept Organ Chem, Zaragoza 50009, Spain

[2] ENSIC, CNRS, UMR 7568, INPL,Lab Macromol Phys Chem, F-54001 Nancy, France

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 15期

关键词：

2,3-methanovaline; constrained amino acid; cyclopropane amino acid; X-ray diffraction; crystal structure; peptide conformation; peptide structure; peptide turn; beta-turn; gamma-turn;

D O I：

10.1016/S0040-4039(03)00514-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyclopropane analogue of valine (1-amino-2,2-dimethylcyclopropanecarboxylic acid, c(3)Val) has been synthesised and incorporated into the model peptides 'BuCO-L-Pro-L-c(3)Val-NH'Pr and 'BUCO-L-Pro-D-c(3)Val-NH'Pr. In the solid state, both dipeptides accommodate a type II beta-turn stabilised by an (NHPr)-Pr-i to 'BuCO hydrogen bond. Remarkably, the peptide incorporating L-c(3)Val also exhibits a distorted gamma-turn around the cyclopropane residue, with Pro-CO and (NHPr)-Pr-i intramolecularly hydrogenbonded. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：3147 / 3150

页数：4

共 28 条

[1] PAPQMD parametrization of molecular systems with cyclopropyl rings: Conformational study of homopeptides constituted by l-aminocyclopropane-l-carboxylic acid [J].