title: 1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics.
abstract: Since the discovery of Cu(I)-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.
authors.affiliation: Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS, Amsterdam, The Netherlands.
authors.forename: Victoria D
authors.initials: VD
authors.lastname: Bock
authors.forename: Dave
authors.initials: D
authors.lastname: Speijer
authors.forename: Henk
authors.initials: H
authors.lastname: Hiemstra
authors.forename: Jan H
authors.initials: JH
authors.lastname: van Maarseveen
mesh_terms: D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D014442:Monophenol Monooxygenase / Q000378:metabolism; D010456:Peptides, Cyclic / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*
chemical_list: D010456:Peptides, Cyclic; D014230:Triazoles; D014442:Monophenol Monooxygenase