1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics
Bock, Victoria D.; Speijer, Dave; Hiemstra, Henk; van Maarseveen, Jan H.; Bock Victoria D.; Van't Hoff Institute for Molecular Sciences, University of Amsterdam; Speijer Dave; Department of Medical Biochemistry, Academic Medical Center, University of Amsterdam; Hiemstra Henk; Van't Hoff Institute for Molecular Sciences, University of Amsterdam; van Maarseveen Jan H.; Van't Hoff Institute for Molecular Sciences, University of Amsterdam
Журнал:
Organic & Biomolecular Chemistry
Дата:
2007
Аннотация:
Since the discovery of Cu<sup>I</sup>-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.
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