Synthesis of a tricyclic hexapeptide -via two consecutive ruthenium-catalyzed macrocyclization steps- with a constrained topology to mimic vancomycin's binding properties toward D-Ala-D-Ala dipeptide.

Bioorg Med Chem Lett

Division of Chemical Biology & Drug Discovery, Utrecht Institute for Pharmaceutical Sciences, Department of Pharmaceutical Sciences, Faculty of Science, Utrecht University, P. O. Box 80082, 3508 TB Utrecht, The Netherlands; School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ, United Kingdom; Maastricht University, Faculty of Medicine, Cardiovascular Research Institute Maastricht, Universiteitssingel 50, 6200 MD Maastricht, The Netherlands. Electronic address:

Published: October 2022

A ring-closing metathesis (RCM) - peptide coupling - ruthenium-catalyzed azide alkyne cycloaddition (RuAAC) strategy was developed to synthesize a tricyclic hexapeptide in which the side chain to side chain connectivity pattern resulted in a mimic with a topology that effectively mimics the bioactivity of vancomycin as a potent binder of the bacterial cell wall D-Ala-D-Ala dipeptide sequence and more importantly being an effective inhibitor of bacterial growth.

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http://dx.doi.org/10.1016/j.bmcl.2022.128887DOI Listing

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