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Title

Solid- and Solution-Phase Synthesis of Vancomycin and Vancomycin Analogues with Activity against Vancomycin-Resistant Bacteria

Authors
Nicolaou, K. C.
Cho, Suk Young
Hughes, Robert
Smethurst, Christian
Labischinski, Harald
Endermann, Rainer
Published in Chemistry - A European Journal. 2001, vol. 7, no. 17, p. 3798-3823
Abstract Vancomycin, the prototypical member of the glycopeptide family of antibiotics, is a clinically used antibiotic employed against a variety of drug-resistant bacterial strains including methicillin-resistant Staphylococcus aureus (MRSA). The recent emergence of vancomycin resistance, viewed as a growing threat to public health, prompted us to initiate a program aimed at restoring the potency of this important antibiotic through chemical manipulation of the vancomycin structure. Herein, we describe the development of synthetic technology based on the design of a novel selenium safety catch linker, application of this technology to a solid-phase semisynthesis of vancomycin, and the solid- and solution-phase synthesis of vancomycin libraries. Biological evaluation of these compound libraries led to the identification of a number of in vitro highly potent antibacterial agents effective against vancomycin-resistant bacteria. In addition to aiding these investigations, the solid-phase chemistry described herein is expected to enhance the power of combinatorial chemistry and facilitate chemical biology and medicinal chemistry studies.
Keywords antibioticsbiological evaluationcombinatorial synthesissynthesis designvancomycin
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NICOLAOU, K. C. et al. Solid- and Solution-Phase Synthesis of Vancomycin and Vancomycin Analogues with Activity against Vancomycin-Resistant Bacteria. In: Chemistry - A European Journal, 2001, vol. 7, n° 17, p. 3798-3823. https://archive-ouverte.unige.ch/unige:24520

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Deposited on : 2012-12-12

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