Aspartame analogues containing 1-amino-2-phenylcyclohexanecarboxylic acids (c6Phe)

被引：4

作者：

Avenoza, A

París, M

Peregrina, JM

Alías, M

López, MP

García, JI

Cativiela, C ^{[1
]}

机构：

[1] Univ Zaragoza, CSIC, Fac Ciencias, Inst Ciencia Mat Aragon,Dept Quim Organ, E-50009 Zaragoza, Spain

[2] Univ La Rioja, CSIC, UA, Grp Sistesis Quim La Rioja,Dept Quim, Logrono 26006, Spain

来源：

TETRAHEDRON | 2002年 / 58卷 / 24期

关键词：

Diels-Alder reactions; cyclohexanes; resolution; chromatography; peptide analogues/mimetics; conformation; computer-assisted methods;

D O I：

10.1016/S0040-4020(02)00435-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This report describes the synthesis and the conformational analysis of the optically pure dipeptides analogues of aspartame: H-(S)-Asp-(1R,2R)-c(6)Phe-OMe and H-(S)-Asp-(1S,2S)-c(6)Phe-OMe, in which the Phe residue of aspartame has been replaced by a restricted Phe with a cyclohexane skeleton: 1-amino-2-phenylcyclohexanecarboxylic acid (c(6)Phe). Of these, only the dipeptide that incorporates (1R,2R)-c(6)Phe is sweet, whereas that incorporates (1S,2S)-c(6)Phe is bitter. This relationship between the absolute configuration of the dipeptides and the properties is explained through the different conformational behaviour displayed by each molecule, based on molecular mechanics and molecular dynamics calculations, including solvent effects. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：4899 / 4905

页数：7

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2-U

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