Structure-activity relationship of daptomycin analogues with substitution at (2S, 3R) 3-methyl glutamic acid position.
Autor: | Lin D; Department of Chemistry, State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Hong Kong Special Administrative Region., Lam HY; Department of Chemistry, State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Hong Kong Special Administrative Region., Han W; Department of Chemistry, State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Hong Kong Special Administrative Region., Cotroneo N; Cubist Pharmaceutical, Inc., 65 Hayden Avenue, Lexington, MA 02421, United States., Pandya BA; Cubist Pharmaceutical, Inc., 65 Hayden Avenue, Lexington, MA 02421, United States. Electronic address: pandya.bhaumik@gmail.com., Li X; Department of Chemistry, State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Hong Kong Special Administrative Region. Electronic address: xuechenl@hku.hk. |
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Jazyk: | angličtina |
Zdroj: | Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2017 Feb 01; Vol. 27 (3), pp. 456-459. Date of Electronic Publication: 2016 Dec 18. |
DOI: | 10.1016/j.bmcl.2016.12.046 |
Abstrakt: | Daptomycin is a highly effective lipopeptide antibiotic against Gram-positive pathogens. The presence of (2S, 3R) 3-methyl glutamic acid (mGlu) in daptomycin has been found to be important to the antibacterial activity. However the role of (2S, 3R) mGlu is yet to be revealed. Herein, we reported the syntheses of three daptomycin analogues with (2S, 3R) mGlu substituted by (2S, 3R) methyl glutamine (mGln), dimethyl glutamic acid and (2S, 3R) ethyl glutamic acid (eGlu), respectively, and their antibacterial activities. The detailed synthesis of dimethyl glutamic acid was also reported. (Copyright © 2016 Elsevier Ltd. All rights reserved.) |
Databáze: | MEDLINE |
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