Structural determination of stevastelins, novel depsipeptides from Penicillium sp

J Antibiot (Tokyo). 1996 Jun;49(6):564-8. doi: 10.7164/antibiotics.49.564.

Abstract

Structures of novel immunosuppressants, stevastelin A, B and B3(1) were determined by their spectroscopic and chemical studies. Three stevastelins were shown to be cyclic depsipeptides composed of a fatty acid and three amino acid moieties. The sequence of these moieties was determined to be as 3,5-dihydroxy-2,4-dimethylstearylvalylthreonyl (or O-sulfonylthreonyl in stevastelin A)-O-acetylserine. Cyclic structures were shown to be formed by ester linkages between the carboxylic group of the O-acetylserine moiety and the 5-hydroxy group of the fatty acid moiety in stevastelin A and B, and the 3-hydroxy group of the fatty acid moiety in stevastelin B3.

Publication types

  • Comparative Study

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Depsipeptides*
  • Fungal Proteins*
  • Immunosuppressive Agents / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Penicillium
  • Peptides*

Substances

  • Anti-Bacterial Agents
  • Depsipeptides
  • Fungal Proteins
  • Immunosuppressive Agents
  • Peptides
  • stevastelin B
  • stevastelin B3
  • stevastelin A