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Alanine scan of [L-Dap2]ramoplanin A2 aglycon:  Assessment of the importance of each residue

Academic Article
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Overview

authors

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

publication date

  • July 2007

journal

  • Journal of the American Chemical Society  Journal

abstract

  • In efforts that define the importance of each residue and that identify key regions of the molecule, an alanine scan of the ramoplanin A2 aglycon, a potent antibiotic that inhibits bacterial cell wall biosynthesis, is detailed. As a consequence of both its increased stability (lactam vs lactone) and its "relative" ease of synthesis, the alanine scan was conducted on [Dap2]ramoplanin A2 aglycon, which possesses antimicrobial activity equal to or slightly more potent than that of ramoplanin A2 or its aglycon. Thus, 14 key analogues of the ramoplanin A2 aglycon, representing a scan of residues 3-13, 15, and 17, were prepared enlisting a convergent solution-phase total synthesis that consolidated the effort to a manageable level. The antimicrobial activity of the resulting library of analogues provides insight into the importance and potential role of each residue of this complex glycopeptide antibiotic.

subject areas

  • Alanine
  • Amino Acids
  • Anti-Bacterial Agents
  • Depsipeptides
  • Glycoproteins
  • Mutagenesis, Site-Directed
  • Peptide Library
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Identity

PubMed Central ID

  • PMC2593884

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja068573k

PubMed ID

  • 17592838
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Additional Document Info

start page

  • 8747

end page

  • 8755

volume

  • 129

issue

  • 28

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