ISOLATION OF NOVEL ANTIBIOTICS X-14667A AND X-14667B FROM STREPTOMYCES CINNAMONENSIS SUBSP. URETHANOFACIENS AND THEIR CHARACTERIZATION AS 2-PHENETHYLURETHANES OF MONENSINS B AND A

• Published in: Journal of antibiotics Vol. 34; no. 10; pp. 1248 - 1252
• Main Authors: WESTLEY, JOHN W., EVANS, RALPH H., Jr, SELLO, LILIAN H., TROUPE, NELSON, LIU, CHAO-MIN, MILLER, PHILIP A.
• Format: Journal Article
• Language: English
• Published: Japan JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 1981
• Subjects: Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - metabolism; Chemical Phenomena; Chemistry; Furans - isolation & purification; Magnetic Resonance Spectroscopy; Mass Spectrometry; Monensin - analogs & derivatives; Monensin - chemical synthesis; Monensin - isolation & purification; Monensin - metabolism; Streptomyces cinnamonensis
• ISSN: 0021-8820; 1881-1469
• DOI: 10.7164/antibiotics.34.1248

Antibiotics X-14667A (1) and X-14667B (2) are novel monovalent polyether antibiotics of the spiroketal type isolated from fermented cultures of Streptomyces cinnamonensis subsp. urethanofaciens together with monensin (3), its lower homolog, factor B (4) and 1, 3-diphenethylurea (6). By a combination of microanalysis, mass spectrometry and 13C nmr, antibiotics X-14667A and B have been shown to be natural 2-phenethylurethanes of monensin B and A respectively. Both structures have been confirmed by reacting the appropriate monensin with 2-phenethylisocyanate to yield semi-synthetic compounds that are identical to the natural products.