Tetrahedron Asymmetry p. 1899 - 1916 (1998)
Update date:2022-08-11
Topics:
Beecher, Jean
Willetts, Andrew
Growth of the bacterium Pseudomonas putida NCIMB 10007 on racemic camphor induces two enantiocomplementary diketocamphane monooxygenase isofunctional enzymes (isozymes) both able to catalyse electrophilic biooxidation of a wide range of prochiral sulfoxides to the corresponding chiral sulfoxides. Active site models to explain and predict the stereoselectivity of the sulfoxidations catalysed by both isozymes are proposed. The models are based on restrictive space descriptors derived from the optimised outcomes obtained with 23 different phenyl alkyl, benzyl alkyl, methyl alkyl and ethyl alkyl sulfides: consistency was maximised by using the same enzyme preparations throughout. The models, which are consistent with the recognised stereoselectivities of diketocamphane monooxygenase catalysed nucleophilic biooxidations of ketones to lactones, are the first to provide insight into the active site topography of FMN plus NADH-dependent Baeyer- Villiger monooxygenases. In addition, they are unique in providing a direct comparison of the active sites of two enantiocomplimentary isofunctional proteins that have evolved in the same cell line.
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