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Total synthesis and structure of the ramoplanin A1 and A3 aglycons: two minor components of the ramoplanin complex

Academic Article
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Overview

authors

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

publication date

  • August 2004

journal

  • Proceedings of the National Academy of Sciences of the United States of America  Journal

abstract

  • Ramoplanin is a potent antibiotic, first disclosed in 1984, that acts by inhibiting bacterial cell-wall biosynthesis. The original ramoplanin complex was shown to consist of a mixture of three closely related compounds, ramoplanin A1-A3, of which ramoplanin A2 is the most abundant. The structure of ramoplanin A2 was unambiguously established first through a series of extensive spectroscopic studies, allowing complete stereochemical assignments and subsequently providing a minor reassignment of the side-chain double-bond stereochemistry and, most recently, through total synthesis of authentic material. Here we report the total syntheses of the aglycons of the minor components of the ramoplanin complex, A1 and A3, which unambiguously establish their structure and provide an expected structural revision for the lipid side-chain double-bond stereochemistry.

subject areas

  • Anti-Bacterial Agents
  • Chemistry, Organic
  • Depsipeptides
  • Molecular Structure
  • Peptides, Cyclic
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC514419

International Standard Serial Number (ISSN)

  • 0027-8424

Digital Object Identifier (DOI)

  • 10.1073/pnas.0401419101

PubMed ID

  • 15175429
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Additional Document Info

start page

  • 11977

end page

  • 11979

volume

  • 101

issue

  • 33

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