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198 showed that when isopenicillin N (1), labelled with 3H in the 3-fi-methyl group, was incubated with extracts of P. chrysogenum in the presence of phenyl acetyl-coenzyme A, eH]-penicillin G (8) was produced. These workers went on to show that, in the absence of phenylacetyl-coenzyme A, when cell-free extracts from P. chrysogenum were incubated with isopenicillin N (1), 6-APA (7) was produced. 199,200 The soluble fractions that catalysed the acyl-coenzyme A: isopenicillin N (1) acyl-transfer and isopenicillin N (1) amidohydrolase activities were also shown to catalyse acyl-coenzyme A : 6-APA (7) acyl transfer with approximately equal efficiency.

38 ~)=(~ . 39 the chemistry of DAOCSIDACS bears a strong similarity to that of IPNS. A major difference is in the stoichiometry of dioxygen utilisation by the two enzymes. For lPNS, an overall four electron oxidation of ACV (2) is achieved, with conversion of one molecule of dioxygen into water. In the case of DAOCSIDACS, for each consecutive step, only a two electron oxidation of the f3-lactam substrate is achieved from each molecule of dioxygen used up, since, in each step, one molecule of a-ketoglutorate is transformed into carbon dioxide and succinate.

A major difference is in the stoichiometry of dioxygen utilisation by the two enzymes. For lPNS, an overall four electron oxidation of ACV (2) is achieved, with conversion of one molecule of dioxygen into water. In the case of DAOCSIDACS, for each consecutive step, only a two electron oxidation of the f3-lactam substrate is achieved from each molecule of dioxygen used up, since, in each step, one molecule of a-ketoglutorate is transformed into carbon dioxide and succinate. 41). The hydroxy cepham (74) results from a reductive elimination process occurring after the rearrangement.

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A textbook of inorganic chemistry vol.X The metal-amines


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