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Issue 6, 2007
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1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics

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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

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Publication details

The article was received on 15 Nov 2006, accepted on 30 Jan 2007 and first published on 06 Feb 2007


Article type: Paper
DOI: 10.1039/B616751A
Org. Biomol. Chem., 2007,5, 971-975

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    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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