Issue 6, 2007

1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics

Abstract

Since the discovery of CuI-catalysed click chemistry, the field of peptidomimetics has expanded to include 1,4-connected 1,2,3-triazoles as useful peptide bond isosteres. Here, we report the synthesis of triazole-containing analogues of the naturally occurring tyrosinase inhibitor cyclo-[Pro-Val-Pro-Tyr] and show that the analogues retain enzyme inhibitory activity, demonstrating the effectiveness of a 1,4-connected 1,2,3-triazole as a trans peptide bond isostere.

Graphical abstract: 1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics

Supplementary files

Article information

Article type
Paper
Submitted
15 Nov 2006
Accepted
30 Jan 2007
First published
06 Feb 2007

Org. Biomol. Chem., 2007,5, 971-975

1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics

V. D. Bock, D. Speijer, H. Hiemstra and J. H. van Maarseveen, Org. Biomol. Chem., 2007, 5, 971 DOI: 10.1039/B616751A

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