Thienamycin, a new beta-lactam antibiotic. I. Discovery, taxonomy, isolation and physical properties.
A new beta-lactam antibiotic, named thienamycin, was discovered in culture broths of Streptomyces MA4297. The producing organism, subsequently determined to be a hitherto unrecognized species, is designated Streptomyces cattleya (NRRL 8057). The antibiotic was isolated by adsorption on Dowex 50, passage through Dowex 1, further chromatography on Dowex 50 and Bio-Gel P2, and final purification and desalting on XAD-2. Thienamycin is zwitterionic, has the elemental composition C11H16N2O4S (M.W. = 272.18) and possesses a distinctive UV absorption (lambda max = 297 nm, epsilon = 7,900). Its beta-lactam is unusually sensitive to hydrolysis above pH8 and to reaction with nucleophiles such as hydroxylamine, cysteine and, to a lesser degree, the primary amine of the antibiotic itself. The latter reaction results in accelerated inactivation at high antibiotic concentrations.
D000900:Anti-Bacterial Agents / Q000096:biosynthesis* / Q000302:isolation & purification; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004355:Drug Stability; D005285:Fermentation; D013302:Streptomyces / Q000145:classification / Q000378:metabolism*; D047090:beta-Lactams / Q000096:biosynthesis / Q000302:isolation & purification
D000900:Anti-Bacterial Agents; D047090:beta-Lactams