Abstract

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.

Keywords

ThienamycinChemistryBeta-lactamHydrolysisNucleophileStreptomycesAmine gas treatingAntibioticsLactamStereochemistryChromatographyOrganic chemistryBacteriaBiologyBiochemistryCatalysis

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Publication Info

Year
1979
Type
article
Volume
32
Issue
1
Pages
1-12
Citations
505
Access
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Jean S. Kahan, Frederick M. Kahan, Robert T. Goegelman et al. (1979). Thienamycin, a new .BETA.-lactam antibiotic. I. Discovery, taxonomy, isolation and physical properties.. The Journal of Antibiotics , 32 (1) , 1-12. https://doi.org/10.7164/antibiotics.32.1

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DOI
10.7164/antibiotics.32.1