Synthesis of microcin SF608

J Org Chem. 2002 Jul 12;67(14):4945-50. doi: 10.1021/jo025709y.

Abstract

The first total synthesis of aquatic peptide microcin SF608 is described. Coupling of L-Hpla with the dipeptide L-Phe-L-Choi followed by coupling with agmatine and a deprotection step gave microcin SF608. In addition, the levorotatory character of L-Hpla (5) was thoroughly established, and the conformational analysis of L-Choi containing peptides 1 and 8-10 was performed using NMR spectroscopy to examine the cis-trans isomer equilibrium of the L-Phe-L-Choi amide bond.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology
  • Bacteriocins / chemistry
  • Catalysis
  • Indoles / chemistry
  • Leucine / analogs & derivatives*
  • Leucine / chemistry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides*
  • Stereoisomerism
  • Trypsin Inhibitors / chemical synthesis*
  • Trypsin Inhibitors / pharmacology

Substances

  • Anti-Bacterial Agents
  • Bacteriocins
  • Indoles
  • Peptides
  • Trypsin Inhibitors
  • aeruginosin 298-A
  • aeruginosin 298-B
  • microcin SF608
  • microcin
  • Leucine