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Silver(I)-promoted conversion of thioamides to amidines: divergent synthesis of a key series of vancomycin aglycon residue 4 amidines that clarify binding behavior to model ligands

Academic Article
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Overview

related to degree

  • James, Robert C., Ph.D. in Biophysics, Scripps Research 2006 - 2012

authors

  • Okano, Akinori
  • James, Robert C.
  • Pierce, J. G.
  • Xie, J.
  • Boger, Dale

publication date

  • May 2012

journal

  • Journal of the American Chemical Society  Journal

abstract

  • Development of a general Ag(I)-promoted reaction for the conversion of thioamides to amidines is disclosed. This reaction was employed to prepare a key series of vancomycin aglycon residue 4 substituted amidines that were used to clarify their interaction with model ligands of peptidoglycan precursors and explore their resulting impact on antimicrobial properties.

subject areas

  • Amidines
  • Anti-Bacterial Agents
  • Bacterial Proteins
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Drug Design
  • Drug Resistance, Bacterial
  • Enterococcus faecalis
  • Ligands
  • Peptidoglycan
  • Silver
  • Thioamides
  • Vancomycin
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Identity

PubMed Central ID

  • PMC3365631

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja302808p

PubMed ID

  • 22568755
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Additional Document Info

start page

  • 8790

end page

  • 8793

volume

  • 134

issue

  • 21

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