The Fe(II)- and 2-oxo-glutarate-dependent enzyme carbapenem synthase (CarC) inverts the configuration of carbon 5 of its substrate; this reaction is a key step in the biosynthesis of carbapenem antibiotics. The structure of CarC in complex with its substrate and biophysical dissection of its reaction by a combination of transient state biophysical methods reveal the mechanism of the stereoinversion. An Fe(IV)-oxo intermediate abstracts hydrogen from C5, and tyrosine 165, a residue not visualized in the published structures of CarC lacking bound substrate, donates a hydrogen atom to the opposite face of the resultant radical.

Mechanism of the C5 stereoinversion reaction catalyzed by the Fe(II)- and 2-oxoglutarate-dependent enzyme, CarC, in the biosynthesis of carbapenem antibiotics

248th National Meeting (2014)

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