Structure of thioviridamide, a novel apoptosis inducer from Streptomyces olivoviridis

J Antibiot (Tokyo). 2006 Jan;59(1):6-10. doi: 10.1038/ja.2006.2.

Abstract

A novel apoptosis inducer, thioviridamide, was isolated from an actinomycete identified as Streptomyces olivoviridis. The molecular formula of thioviridamide was determined to be C56H93N14O10S7+ from high-resolution FAB-MS. The structure of thioviridamide was analyzed by NMR spectral analysis including a variety of two-dimensional techniques. COSY and HMBC experiments revealed the presence of a 2-hydroxy-2-methyl-4-oxopentanoyl group and eleven amino acid residues including two novel amino acids, beta-hydroxy-N1,N3-dimethylhistidinium and S-(2-aminovinyl)cysteine. 1H-13C long-range correlations observed in the HMBC, CT-HMBC and HMBC-HOHAHA spectra connected the partial structures with seven amide linkages and five thioamide linkages to establish the planar structure of thioviridamide as a unique cyclic peptide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / analysis
  • Antibiotics, Antineoplastic / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Peptides, Cyclic / chemistry*
  • Spectrometry, Mass, Fast Atom Bombardment
  • Thioamides / chemistry*

Substances

  • Amino Acids
  • Antibiotics, Antineoplastic
  • Peptides, Cyclic
  • Thioamides
  • thioviridamide