New cyclic depsipeptide antibiotics, clavariopsins A and B, produced by an aquatic hyphomycetes, Clavariopsis aquatica. 2. Structure analysis

The structures of new cyclic decadepsipeptides, clavariopsins A and B, were determined to be cyclo[-(R)-2-hydroxyisovaleryl-L-pipecoyl-L-MeVal-L-Val-L-MeAsp-L-MeIle-L-MeIle-Gly L-MeVal-L-Tyr(OMe)-] and cyclo[-(R)-2-hydroxyisovaleryl-L-pipecolyl-L-Val-L-Val-L-MeAsp-L-Melle-L-MeIle-Gly-L-MeVal-L-Tyr(O...

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Bibliographic Details
Published in:Journal of antibiotics 2001-01, Vol.54 (1), p.22-28
Main Authors: SUZUKI, Yoshihiro, OJIKA, Makoto, SAKAGAMI, Youji, KAIDA, Kenichi, FUDOU, Ryosuke, KAMEYAMA, Toshiyuki
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemistry
Antibiotics (antibacterial agents, antifungal agents)
Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents
Applied microbiology
Biological and medical sciences
Chromatography, High Pressure Liquid
Fundamental and applied biological sciences. Psychology
Magnetic Resonance Spectroscopy
Microbiology
Mitosporic Fungi - metabolism
Molecular Conformation
Molecular Structure
Peptides
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Summary:The structures of new cyclic decadepsipeptides, clavariopsins A and B, were determined to be cyclo[-(R)-2-hydroxyisovaleryl-L-pipecoyl-L-MeVal-L-Val-L-MeAsp-L-MeIle-L-MeIle-Gly L-MeVal-L-Tyr(OMe)-] and cyclo[-(R)-2-hydroxyisovaleryl-L-pipecolyl-L-Val-L-Val-L-MeAsp-L-Melle-L-MeIle-Gly-L-MeVal-L-Tyr(OMe)-], respectively, by spectroscopic analyses, especially using 2D NMR techniques. The absolute stereochemistry was elucidated by the advanced Marfey's method and chiral HPLC analysis.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.54.22