Total synthesis of azumamide E and sugar amino acid-containing analogue

J Org Chem. 2009 Jan 2;74(1):401-4. doi: 10.1021/jo8020264.

Abstract

An efficient and practical total synthesis of marine cyclic tetrapeptide, natural product azumamide E (1) is achieved via high-yielding reactions. The strategy also allowed us to synthesize the azumamide E-SAA (sugar amino acid) analogue (2), whose solution-phase NMR and biological activity studies were also carried out.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Carbohydrates / chemistry*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry*
  • Stereoisomerism

Substances

  • Amino Acids
  • Carbohydrates
  • Peptides, Cyclic
  • azumamide E