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Incubation of [2-13C, 3-2H]penicillin N 1c and [4-2H]exomethylene cephalosporin C 5b with the enzyme deacetoxy-/deacetylcephalosporin C synthase (DAOC/DAC synthase) in 18O-labelled water gave oxygenated products showing significant incorporation of 18O; the observed levels of incorporation from 18O-labelled water are complementary to the previously reported incorporations which were achieved from molecular oxygen, and we believe this to be a first example of H218O incorporation into enzymic products catalysed by a non-haem iron, α-ketoglutarate dependent dioxygenase, and suggest structures for the exchanging intermediates.

Original publication




Journal article


Journal of the Chemical Society, Chemical Communications

Publication Date



105 - 108