Conversion of nocathiacin I to nocathiacin acid by a mild and selective cleavage of dehydroalanine. Academic Article uri icon

Overview

abstract

  • Thiazolyl peptide antibiotic nocathiacin I (1) was converted to nocathiacin acid (4) in high yield by treatment with trifluoroacetic anhydride and pyridine in THF at room temperature. Two equipotent water-soluble amide analogues of nocathiacin I were readily prepared from this important and versatile carboxylic acid intermediate under mild peptide coupling conditions. The present method is useful for chemical derivatization of complex natural products that contain C-terminal dehydroalanine.

publication date

  • August 18, 2007

Research

keywords

  • Alanine
  • Carboxylic Acids
  • Peptides
  • Peptides, Cyclic
  • Thiazoles

Identity

Scopus Document Identifier

  • 34548780205

Digital Object Identifier (DOI)

  • 10.1021/jo071115p

PubMed ID

  • 17705543

Additional Document Info

volume

  • 72

issue

  • 19