Issue 28, 2013

An efficient chemical synthesis of carboxylate-isostere analogs of daptomycin

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

Supplementary files

Article information

Article type
Paper
Submitted
02 mei 2013
Accepted
28 mei 2013
First published
29 mei 2013

Org. Biomol. Chem., 2013,11, 4680-4685

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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