The synthesis of benzylpenicillin and 6-aminopenicillanic acid, labeled with tritium in the beta-methyl group, is described. Benzylpenicillin S-sulfoxide benzyl ester is refluxed in benzene and tritiated water and is successively debenzylated and deoxygenated to (beta-methyl-3H)-benzylpenicillin. Removal of the side chain with a bacterial acylase gives (beta-methyl-3H)-6-aminopenicillanic acid.
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Meesschaert et al. (1976) studied this question.
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