Issue 18, 2004

Ring-closing metathesis for the synthesis of side chain knotted pentapeptides inspired by vancomycin

Abstract

A versatile method for the synthesis of bicyclic side chain knotted peptides inspired by vancomycin is described. The synthetic approach is based on the incorporation of a central amino acid derivative 3 having two allylic groups—introduced by a Stille coupling—into pentapeptide 8 containing two allylated serine residues. Treatment of this bis-ring-closing metathesis precursor with 2nd generation Grubbs catalyst results in the formation of a bicyclic pentapeptide with the correct side chain to side chain connectivity pattern as observed in vancomycin: i − 2 → i, ii + 2. Modelling studies using MacroModel hint at a cavity-like structure of the bicyclic pentapeptide which may bind suitable ligands.

Graphical abstract: Ring-closing metathesis for the synthesis of side chain knotted pentapeptides inspired by vancomycin

Article information

Article type
Paper
Submitted
11 Jun 2004
Accepted
03 Aug 2004
First published
24 Aug 2004

Org. Biomol. Chem., 2004,2, 2658-2663

Ring-closing metathesis for the synthesis of side chain knotted pentapeptides inspired by vancomycin

H. T. ten Brink, D. T. S. Rijkers, J. Kemmink, H. W. Hilbers and R. M. J. Liskamp, Org. Biomol. Chem., 2004, 2, 2658 DOI: 10.1039/B408820D

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