Issue 12, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Multicomponent synthesis of tripeptides containing pipecolic acid derivatives: selective induction of cis- and trans-imide bonds into peptide backbones

Wolfgang Maison,a   Arne Lützen,a   Marc Kosten,a   Imre Schlemminger,a   Ole Westerhoff,a   Wolfgang Saaka  and  Jürgen Martens*a  

* Corresponding authors

a Department of Chemistry, University of Oldenburg, Oldenburg, Germany

Abstract

A simple approach to several tripeptides consisting of two terminal glycine fragments and a central pipecolic acid derivative was found via a multicomponent reaction starting from tetrahydropyridines. The protected peptides 2a–g were formed in high yields and with different substitution patterns of the central heterocyclic amino acid. In cases where chiral imines were used the target compounds were obtained with remarkable diastereoselectivity. The influence of different substituents attached to the pipecolic acid fragment on N-terminal amide isomerism was investigated using X-ray crystallography and NMR spectroscopic methods.

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B002258F
Article type
Paper
Submitted
21 Mar 2000
Accepted
28 Apr 2000
First published
02 Jun 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 1867-1871

Permissions

Request permissions

Multicomponent synthesis of tripeptides containing pipecolic acid derivatives: selective induction of cis- and trans-imide bonds into peptide backbones

W. Maison, A. Lützen, M. Kosten, I. Schlemminger, O. Westerhoff, W. Saak and J. Martens, J. Chem. Soc., Perkin Trans. 1, 2000, 1867 DOI: 10.1039/B002258F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements