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Streptocidins A-D, Novel Cyclic Decapeptide Antibiotics Produced by Streptomyces sp. Tue 6071. II. Structure Elucidation.
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- HÖLTZEL ALEXANDRA
- Institut für Organische Chemie, Universität Tübingen
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- JACK RALPH W.
- Institut für Organische Chemie, Universität Tübingen EMC Microcollections GmbH Present address: Department of Biology and Chemistry, Centre for Coastal Pollution and Conservation, The City University of Hong Kong
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- NICHOLSON GRAEME J.
- Institut für Organische Chemie, Universität Tübingen
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- JUNG GÜNTHER
- Institut für Organische Chemie, Universität Tübingen
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- GEBHARDT KLAUS
- Mikrobio logisches Institut, Universität Tübingen
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- FIEDLER HANS-PETER
- Mikrobio logisches Institut, Universität Tübingen
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- SÜSSMUTH RODERICH D.
- Institut für Organische Chemie, Universität Tübingen
Bibliographic Information
- Other Title
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- II. Structure Elucidation
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Description
The structures of the new antibiotics Streptocidins A-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 (G). The amino acid composition (including the configuration) of the substances was determined by chiralphase GC-MS of the hydrolysates. The sequences were established by EDMAN degradation following linearisation of the cyclic peptides upon treatment with LiAIH4. 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.
Journal
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- The Journal of Antibiotics
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The Journal of Antibiotics 54 (5), 434-440, 2001
JAPAN ANTIBIOTICS RESEARCH ASSOCIATION