Kettapeptin: Isolation, structure elucidation and activity of a new hexadepsipeptide antibiotic from a terrestrial Streptomyces sp

• Published in: Journal of antibiotics Vol. 59; no. 5; pp. 309 - 314
• Main Authors: Maskey, Rajendra P., Fotso, Serge, Sevvana, Madhumati, Uson, Isabel, Gruen-Wollny, Iris, Laatsch, Hartmut
• Format: Journal Article
• Language: English
• Published: TOKYO Japan Antibiotics Research Assoc 01.05.2006; Nature Publishing Group
• Subjects: Anti-Infective Agents - chemistry; Anti-Infective Agents - isolation & purification; Anti-Infective Agents - pharmacology; Antibiotics, Antineoplastic - chemistry; Antibiotics, Antineoplastic - isolation & purification; Antibiotics, Antineoplastic - pharmacology; Biotechnology & Applied Microbiology; Cell Line, Tumor; Crystallography, X-Ray; Depsipeptides - chemistry; Depsipeptides - isolation & purification; Depsipeptides - pharmacology; Humans; Immunology; Life Sciences & Biomedicine; Microbial Sensitivity Tests; Microbiology; Models, Molecular; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Optical Rotation; Peptides, Cyclic - chemistry; Peptides, Cyclic - isolation & purification; Peptides, Cyclic - pharmacology; Pharmacology & Pharmacy; Science & Technology; Spectrometry, Mass, Electrospray Ionization; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet; Streptomyces; Streptomyces - chemistry; antibiotic; A83586C; azinothricin; GE3; peptide lactone; DEPSIPEPTIDE ANTIBIOTICS; CITROPEPTIN; cytotoxic; kettapeptin
• ISSN: 0021-8820; 1881-1469
• DOI: 10.1038/ja.2006.44

The ethyl acetate extract of the Streptomyces sp. isolate GW99/1572 exhibited significant biological activity against Grain-positive bacteria and delivered kettapeptin (1), a new hexadepsipeptide antibiotic of the azinothricin type. The structure was elucidated by various 1D and 2D NMR techniques, mass spectrometry and by comparison of the NMR data with those of closely related antibiotics. The absolute configuration of the compound was derived by crystal structure analysis and by comparison with the optical rotation data of related compounds.