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.2022.128887 | DOI Listing |
Bioorg Med Chem Lett
October 2022
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:
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.
View Article and Find Full Text PDFBiosci Biotechnol Biochem
July 2007
Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya, Japan.
Bacillus mojavensis strain RO-H-1 produces a posttranslationally modified hexapeptide, the ComX(RO-H-1) pheromone, that stimulates natural genetic competence controlled by quorum sensing. LC/ESI-MS analysis of partially purification of the ComX(RO-H-1) pheromone suggested a precise modification in its tryptophan residue. The corresponding ComX(RO-H-1) pheromone prepared by solid-phase synthesis was identical to the natural pheromone, and showed significant biological activity.
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