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Total synthesis and examination of three key analogues of ramoplanin: a lipoglycodepsipeptide with potent antibiotic activity

Academic Article
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Overview

authors

  • Rew, Y.
  • Shin, D.
  • Hwang, I.
  • Boger, Dale

publication date

  • February 2004

journal

  • Journal of the American Chemical Society  Journal

abstract

  • The total synthesis and evaluation of three key ramoplanin aglycon analogues are detailed. The first (5a) represents replacement of the labile depsipeptide ester with a stable amide (HAsn2 --> Dap2) with removal of the HAsn pendant carboxamide, and it was found to be slightly more potent than the natural aglycon in antimicrobial assays providing a new lead structure with an improved profile and a more stable and accessible macrocyclic template on which to conduct structure-function studies. In contrast, a second amide analogue 5b which contains a single additional methylene relative to 5a (HAsn2 --> Dab2) was found to be inactive in antimicrobial assays (>100-fold loss in activity). The third key analogue 5c in which the Asn1 lipid side chain was replaced with an acetyl group revealed that it contributes significantly to the antimicrobial activity (16-fold) of the ramoplanins, but is not essential.

subject areas

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Depsipeptides
  • Glycopeptides
  • Microbial Sensitivity Tests
  • Peptides, Cyclic
  • Staphylococcus aureus
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja039671y

PubMed ID

  • 14746470
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Additional Document Info

start page

  • 1041

end page

  • 1043

volume

  • 126

issue

  • 4

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