Streptocidins A-D, novel cyclic decapeptide antibiotics produced by Streptomyces sp. Tü 6071. II. Structure elucidation.
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.
Höltzel
A
A
Institut für Organische Chemie, Universität Tübingen, Germany.
Jack
R W
RW
Nicholson
G J
GJ
Jung
G
G
Gebhardt
K
K
Fiedler
H P
HP
Süssmuth
R D
RD
D000595:Amino Acid Sequence; D000596:Amino Acids / Q000032:analysis; D000900:Anti-Bacterial Agents / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D010456:Peptides, Cyclic / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology*; D017433:Protein Structure, Secondary; D020539:Sequence Analysis, Protein; D021241:Spectrometry, Mass, Electrospray Ionization; D013302:Streptomyces / Q000737:chemistry* / Q000378:metabolism
D000596:Amino Acids; D000900:Anti-Bacterial Agents; D010456:Peptides, Cyclic; C433010:streptocidin A; C433011:streptocidin B; C433009:streptocidin C; C433008:streptocidin D