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  • Title: Chromatographic separation and chemical analysis of polymers formed by penicillin G.
    Author: Ueno H, Nishikawa M, Suzuki S, Muranaka M.
    Journal: J Chromatogr; 1984 Apr 20; 288(1):117-26. PubMed ID: 6725468.
    Abstract:
    To elucidate the chemical structures of penicillin polymers that may elicit an allergic reaction, a 25% aqueous solution of penicillin G potassium was kept standing in the dark at room temperature for 14 days and was then separated by gel filtration chromatography on Sephadex G-25. The fractions of Kav 0.0-0.3, 0.3-0.55 and 0.55-0.75 were designated fractions A, B and C, respectively. Chemical and spectral data indicated that fractions A and B had almost similar chemical structures, but differed in molecular weight. They consisted of equimolar phenylacetyl and thiazolidine moieties and showed a C:N:S ratio almost equal to that of penicillin G. Their degrees of polymerization were 10 for A and 3.2 for B. Comparison of 1H NMR and IR spectra and thin-layer chromatographic RF values with those of authentic standards showed that the main components of fraction C were N- formylpenicillamine , benzylpenilloic acid, benzylpenicilloic acid and benzylpenillic acid.
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