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Open Access Design and Synthesis of 16-Membered Cyclopeptides Active Against Vancomycin-resistant Enterococci (VRE)

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The design, synthesis and antibiotic activities of the modified carboxylate binding pocket (D-O-E ring) of vancomycin (1) are summarized in this short account. The preliminary structure–activity relationship (SAR) studies indicated that both the structure of the 16-membered macrocycle including the absolute configuration of the modified AA4 unit and the presence of a hydrophobic chain were important for anti-VRE activities of these series of synthetic analogues. Compounds 9c and 9d in which the central amino acid (AA4) of vancomycin was replaced by (2R,3R)-α-hydroxy-β-amino acid and (2R,3R)-α,β-diamino acid, respectively, were found to be useful templates in searching for active compounds against both vancomycin-sensitive and -resistant strains. Two of these compounds (16d and 16n) having an elongated peptide chain at the C-terminal were found to be active against a broad spectrum of both vancomycin-sensitive (Staphylococcus aureus) and -resistant strains (E. faecium, E. faecalis).

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Keywords: ANTIBIOTIC; CYCLOPEPTIDE; MACROCYCLE; SNAR REACTION; VANCOMYCIN

Document Type: Research Article

Affiliations: Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, CH-1015 Lausanne, Switzerland

Publication date: December 1, 2013

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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