Sanglifehrins A, B, C and D, Novel Cyclophilin-Binding Compounds Isolated From Streptomyces Sp. A92-308110. II. Structure Elucidation, Stereochemistry and Physico-Chemical Properties

J Antibiot (Tokyo). 1999 May;52(5):474-9. doi: 10.7164/antibiotics.52.474.

Abstract

A novel class of macrolides, the sanglifehrins, was discovered by screening of actinomycete strains with a cyclophilin-binding assay. The chemical structures and absolute stereochemistries of the sanglifehrins A, B, C and D were determined unambiguously by NMR-techniques and by X-ray crystallography of the complex with cyclophilin A. Sanglifehrin A consists of a 22-membered macrocycle containing a tripeptide subunit and features in position 23 a chain of nine carbon atoms bearing a spirocyclic substituent. Sanglifehrins A and B are genuine metabolites whereas sanglifehrins C and D are artefacts.

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / metabolism
  • Crystallography, X-Ray
  • Immunosuppressive Agents / chemistry*
  • Immunosuppressive Agents / isolation & purification
  • Immunosuppressive Agents / metabolism
  • Lactones / chemistry
  • Macrolides
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Molecular Structure
  • Peptidylprolyl Isomerase / metabolism
  • Spiro Compounds / chemistry
  • Streptomyces / metabolism*

Substances

  • Anti-Bacterial Agents
  • Immunosuppressive Agents
  • Lactones
  • Macrolides
  • Spiro Compounds
  • sanglifehrin A
  • sanglifehrin B
  • sanglifehrin C
  • sanglifehrin D
  • Peptidylprolyl Isomerase