Solid phase synthesis of vancomycin mimics

Christopher J. Arnusch, Roland J. Pieters

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

A solid phase synthesis of a model system of the DE ring system of vancomycin is described. The synthesis involved biocatalytic resolutions of unnatural amino acids, is compatible with conventional solid phase peptide synthesis and contains as the key step: an on-be.ad SNAr cyclization. Binding of a cyclic peptide to the carboxylate of N-Ac-D-Ala was demonstrated.

Original languageEnglish
Pages (from-to)3131-3138
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number16
DOIs
StatePublished - 11 Aug 2003
Externally publishedYes

Keywords

  • Antibiotics
  • Bioorganic chemistry
  • Cyclization
  • Peptides
  • Receptors

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