The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
THIENAMYCIN, A NEW β-LACTAM ANTIBIOTIC I. DISCOVERY, TAXONOMY, ISOLATION AND PHYSICAL PROPERTIES
J. S. KAHANF. M. KAHANR. GOEGELMANS. A. CURRIEM. JACKSONE. O. STAPLEYT. W. MILLERA. K. MILLERD. HENDLINS. MOCHALESS. HERNANDEZH. B. WOODRUFFJ. BIRNBAUM
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1979 Volume 32 Issue 1 Pages 1-12

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Abstract

A new β-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 (λmax=297 nm, ε=7, 900). Its β-lactam is unusually sensitive to hydrolysis above pH 8 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.

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