Synthesis of (beta-methyl-3H-)-benzylpenicillin and (beta-methyl-3H)-6-aminopenicillanic acid.
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.
D004926:Escherichia coli / Q000378:metabolism; D008722:Methods; D010397:Penicillanic Acid / Q000138:chemical synthesis* / Q000378:metabolism; D010400:Penicillin G / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism
D010397:Penicillanic Acid; D010400:Penicillin G