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N-acetyl-N'-methylamide derivative of (2S,3S)-1-amino-2,3-diphenylcyclopropanecarboxylic acid: theoretical analysis of the conformational impact produced by the incorporation of the second phenyl group to the cyclopropane analogue of phenylalanine.

作者信息

Casanovas Jordi, Jiménez Ana I, Cativiela Carlos, Pérez Juan J, Alemán Carlos

机构信息

Departament de Química, Escola Universitària Politècnica, Universitat de Lleida, c/Jaume II No. 69, 25001 Lleida, Spain.

出版信息

J Org Chem. 2003 Sep 5;68(18):7088-91. doi: 10.1021/jo034720a.

DOI:10.1021/jo034720a
PMID:12946154
Abstract

The intrinsic conformational preferences of (2S,3S)-1-amino-2,3-diphenylcyclopropanecarboxylic acid, a phenylalanine cyclopropane analogue bearing two phenyl substituents, have been examined theoretically. For this purpose, its N-acetyl-N'-methylamide derivative, Ac-(2S,3S)c(3)diPhe-NHMe, has been investigated by using ab initio HF and DFT methods. Results have been compared with those previously reported for other cyclopropane analogues of phenylalanine, and with experimental data available for c(3)diPhe-containing peptides.

摘要

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