A novel cis-peptide bond motif inducing beta-turn type VI. The synthesis of enkephalin analogues modified with 4-aminopyroglutamic acid.

K Kaczmarek; M Kaleta; N N Chung; P W Schiller; J Zabrocki

doi:10.18388/abp.2001_3884

A novel cis-peptide bond motif inducing beta-turn type VI. The synthesis of enkephalin analogues modified with 4-aminopyroglutamic acid.

K Kaczmarek Institute of Organic Chemistry, Technical University of Lódź, Poland.;
M Kaleta
N N Chung
P W Schiller
J Zabrocki

DOI: https://doi.org/10.18388/abp.2001_3884

Abstract

A new pathway leading to a mixture of four isomers of 4-aminopyroglutamic acid is described. Michael type addition of Z-deltaAla-OMe to enolates prepared from acylaminomalonates, followed by hydrolysis and decarboxylation give protected 4-aminopyroglutamic acid with the cis:trans ratio approximately 3:2. This mixture was incorporated into Leu-enkephalin (position 2-3). After separation of peptides it appeared that all analogues were essentially inactive in guinea pig ileum and mouse vas deferens bioassays.

Published

2001-12-31

Issue

Vol. 48 No. 4 (2001)

Section

Articles

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