(a) Penicillin-resistant strains of bacteria contain β-lactamases, enzymes that catalyze the hydrolysis of a penicillin before the penicillin can acylate transpeptidase. Suggest a reasonable structure for the product C16H20N2O5S formed by β-lactamase-catalyzed hydrolysis of penicillin G.
(b) 6-Aminopenicillanic acid (C8H12N2O3S), a key compound in the preparation of “semisynthetic” penicillins, is prepared from penicillin G by penicillin acyl transferase-catalyzed hydrolysis. Suggest a reasonable structure for 6-aminopenicillanic acid.
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