PNEUMOCANDINS FROM Zalerion arboricola: III. STRUCTURE ELUCIDATION

• Published in: Journal of antibiotics 1992/12/25, Vol.45(12), pp.1875-1885
• Main Authors: HENSENS, OTTO D., LIESCH, JERROLD M., ZINK, DEBORAH L., SMITH, JACK L., WICHMANN, CAROL F., SCHWARTZ, ROBERT E.
• Format: Article
• Language: English
• Subjects: Anti-Bacterial Agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antifungal agents; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Antiviral Agents - chemistry; Biological and medical sciences; Candida albicans - drug effects; Crystallography; Echinocandins; Magnetic Resonance Spectroscopy; Medical sciences; Mitosporic Fungi - chemistry; Peptides; Peptides, Cyclic - chemistry; Peptides, Cyclic - pharmacology; Pharmacology. Drug treatments; Pneumocystis - drug effects; Stereoisomerism; Structure-Activity Relationship
• ISSN: 0021-8820; 1881-1469
• DOI: 10.7164/antibiotics.45.1875

Pneumocandin B0 (6) and six related lipopeptides are antifungal and anti-Pneumocystis carinii agents from mutants of Zalerion arboricola, whose structures were determined mainly on the basis of spectroscopic analysis. They belong, along with pneumocandin A0 (L-671, 329) previously isolated from these laboratories, 1) to the echinocandin class of antifungal agents. The product from base-catalyzed ring opening involving the hemiaminal position of the dihydroxyornithine residue of B0, has been clearly defined as 6b. Modifications were limited to the 3-hydroxy-4-methylproline, 3, 4-dihydroxyhomotyrosine and 4, 5-dihydroxyornithine residues of pneumocandin A0.