Rhodopeptins, novel cyclic tetrapeptides with antifungal activities from Rhodococcus sp. II. Structure elucidation

The structures of rhodopeptins, novel antifungal peptides, were determined on the basis of physico-chemical analyses of the intact molecules and their acid hydrolysates. The structures of rhodopeptins C1, C2, C3, C4 and B5 were determined to be cyclo (-Gly-L-Orn-L-Val-3-amino-10-methyldodecanoyl-),...

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Bibliographic Details
Published in:Journal of antibiotics 1999-08, Vol.52 (8), p.700-709
Main Authors: CHIBA, H, AGEMATU, H, DOBASHI, K, YOSHIOKA, T
Format: Article
Language:English
Subjects:
Amino Acid Sequence
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antifungal agents
Antifungal Agents - chemistry
Biological and medical sciences
Magnetic Resonance Spectroscopy
Medical sciences
Molecular Structure
Peptides, Cyclic - chemistry
Peptides, Cyclic - isolation & purification
Peptides, Cyclic - pharmacology
Pharmacology. Drug treatments
Rhodococcus
Rhodococcus - metabolism
rhodopeptin B5
rhodopeptin C1
rhodopeptin C2
rhodopeptin C3
rhodopeptin C4
Spectrometry, Mass, Fast Atom Bombardment
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Summary:The structures of rhodopeptins, novel antifungal peptides, were determined on the basis of physico-chemical analyses of the intact molecules and their acid hydrolysates. The structures of rhodopeptins C1, C2, C3, C4 and B5 were determined to be cyclo (-Gly-L-Orn-L-Val-3-amino-10-methyldodecanoyl-), cyclo (-Gly-L-Orn-L-Ile-3-amino-10-methyldodecanoyl-), cyclo (-Gly-L-Orn-L-Val-3-amino-12-methyltridecanoyl-), cyclo (-Gly-L-Orn-L-Val-3-amino- 12-methyltetradecanoyl-) and cyclo (-Gly-L-Lys-L-Val-3-amino-13-methyltetradecanoyl-), respectively. They are novel cyclic tetrapeptides containing a lipophilic beta-amino acid.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.52.700