Streptocidins A-D, novel cyclic decapeptide antibiotics produced by Streptomyces sp. Tü 6071. II. Structure elucidation

J Antibiot (Tokyo). 2001 May;54(5):434-40. doi: 10.7164/antibiotics.54.434.


The structures of the new antibiotics streptocidins A approximately D were elucidated as cyclic decapeptides cyclo[L-Val1-L-Orn2-L-Leu3-D-Phe4-L-Pro5-L-Leu6-X7-L-Asn8-L-Gln9-X10] with X7=D-Trp (A, B, C) or D-Phe (D) and X10=L-Tyr (A), L-Trp (B, D), or D-Trp (C). The amino acid composition (including the configuration) of the substances was determined by chiral-phase GC-MS of the hydrolysates. The sequences were established by EDMAN degradation following linearisation of the cyclic peptides upon treatment with LiAlH4. NMR spectroscopic studies of streptocidins C and D confirmed the proposed sequences and provided conformational data which indicate a molecular topology of streptocidins C and D similar to those of tyrocidine A and gramicidin S.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Amino Acids / analysis
  • Anti-Bacterial Agents / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Magnetic Resonance Spectroscopy
  • Peptides, Cyclic / chemistry*
  • Peptides, Cyclic / isolation & purification*
  • Peptides, Cyclic / pharmacology*
  • Protein Structure, Secondary
  • Sequence Analysis, Protein
  • Spectrometry, Mass, Electrospray Ionization
  • Streptomyces / chemistry*
  • Streptomyces / metabolism


  • Amino Acids
  • Anti-Bacterial Agents
  • Peptides, Cyclic
  • streptocidin A
  • streptocidin B
  • streptocidin C
  • streptocidin D