1. Phenoxymethylpenicillin sulphoxide 4-methoxybenzyl ester was labelled with 3H in its 2-β-methyl group. Its specific radioactivity was 362 mCi/mmol. 2. Removal of the side chain of this compound yielded the corresponding ester of 6-aminopenicillanic acid sulphoxide and coupling of the latter with the appropriate protected α-aminoadipic acid gave 4-methoxybenzyloxycarbonylisopenicillin N sulphoxide di-4-methoxybenzyl ester or the corresponding derivative of penicillin N. 3. Removal of the protective groups by hydrogenolysis and reduction of the sulphoxide group yielded 3H-labelled isopenicillin N or penicillin N. 4. 3H-labelled phenoxymethylpenicillin sulphoxide was obtained by hydrogenolysis from its 4-methoxybenzyl ester. Reduction of its sulphoxide group and subsequent removal of the side chain gave 3H-labelled 6-aminopenicillanic acid.
Research Article|December 01 1975
Synthesis of tritium-labelled isopenicillin N, penicillin N and 6-aminopenicillanic acid
J J Usher;
Biochem J (1975) 151 (3): 729-739.
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J J Usher, B Loder, E P Abraham; Synthesis of tritium-labelled isopenicillin N, penicillin N and 6-aminopenicillanic acid. Biochem J 1 December 1975; 151 (3): 729–739. doi: https://doi.org/10.1042/bj1510729
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