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Issue 28, 2013
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An efficient chemical synthesis of carboxylate-isostere analogs of daptomycin

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Abstract

Herein we report a direct and efficient method for the synthesis of four new carboxylate-isostere analogs of daptomycin. The side chain carboxylic acid moieties of the aspartic acids (Asp-3, Asp-7 and Asp-9) and β-methyl glutamic acid (MeGlu-12) were all converted into the corresponding carboxylate isosteres using direct synthetic procedures. The present study also describes an esterification protocol to overcome the possible backbone cyclization of the activated side chain carboxylic acid group of either Asp or Glu onto the backbone amide.

Graphical abstract: An efficient chemical synthesis of carboxylate-isostere analogs of daptomycin

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Publication details

The article was received on 02 May 2013, accepted on 28 May 2013 and first published on 29 May 2013


Article type: Paper
DOI: 10.1039/C3OB40924D
Citation: Org. Biomol. Chem., 2013,11, 4680-4685
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    An efficient chemical synthesis of carboxylate-isostere analogs of daptomycin

    S. Yoganathan, N. Yin, Y. He, M. F. Mesleh, Y. Gui Gu and S. J. Miller, Org. Biomol. Chem., 2013, 11, 4680
    DOI: 10.1039/C3OB40924D

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