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Issue 8, 2014
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Anti-bacterial glycosyl triazoles – identification of an N-acetylglucosamine derivative with bacteriostatic activity against Bacillus

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Abstract

N-Acetylglucosaminidases (GlcNAcases) play an important role in the remodeling and recycling of bacterial peptidoglycan. Inhibitors of bacterial GlcNAcases can serve as antibacterial agents and provide an opportunity for the development of new antibiotics. We report the synthesis of triazole derivatives of N-acetylglucosamine using a copper promoted azide–alkyne coupling reaction between 1-azido-N-acetylglucosamine and a small library of terminal alkynes prepared via the Ugi reaction. These compounds were evaluated for their ability to inhibit the growth of bacteria. Two compounds that show bacteriostatic activity against Bacillus were identified, with MIC values of approximately 60 μM in both cases. Bacillus subtilis cultured in the presence of sub-MIC amounts of the glycosyl triazole inhibitors exhibit an elongated phenotype characteristic of impaired cell division. This represents the first report of inhibitors of bacterial cell wall GlcNAcases that demonstrate inhibition of cell growth in whole cell assays.

Graphical abstract: Anti-bacterial glycosyl triazoles – identification of an N-acetylglucosamine derivative with bacteriostatic activity against Bacillus

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Publication details

The article was received on 18 Mar 2014, accepted on 07 May 2014 and first published on 08 May 2014


Article type: Concise Article
DOI: 10.1039/C4MD00127C
Citation: Med. Chem. Commun., 2014,5, 1213-1217
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    Anti-bacterial glycosyl triazoles – identification of an N-acetylglucosamine derivative with bacteriostatic activity against Bacillus

    H. Kuhn, D. Gutelius, E. Black, C. Nadolny, A. Basu and C. Reid, Med. Chem. Commun., 2014, 5, 1213
    DOI: 10.1039/C4MD00127C

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