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Synthesis of the chlorofusin cyclic peptide: assignment of the asparagine stereochemistry

Academic Article
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Overview

authors

  • Desai, P.
  • Pfeiffer, S. S.
  • Boger, Dale

publication date

  • December 2003

journal

  • Organic Letters  Journal

abstract

  • An efficient synthesis of two diastereomers of the chlorofusin cyclic peptide bearing either the l-Asn3/d-Asn-4 or d-Asn3/l-Asn4 stereochemistry is detailed. Four key subunits were prepared, sequentially coupled, and cyclized to provide the two diastereomeric macrocycles. The absolute stereochemistry at the asparagine residues 3 and 4 was assigned as l and d, respectively, by correlating the NMR data of the two diastereomers with that reported for the natural product. [structure: see text]

subject areas

  • Amino Acids
  • Asparagine
  • Cyclization
  • Magnetic Resonance Spectroscopy
  • Peptides, Cyclic
  • Protein Conformation
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol036083g

PubMed ID

  • 14682761
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Additional Document Info

start page

  • 5047

end page

  • 5050

volume

  • 5

issue

  • 26

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