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Productivity enhancement of biocatalysed enantioselective C=C reductions The bioreduction of alphabrocine from whole cells to isolated enzymes

FABIO PARMEGGIANI
Politecnico di Milano – Dipartimento di Chimica, Materiali e Ingegneria Chimica “G. Natta”Via Mancinelli 7, Milano 20131, Italy

Abstract

The industrial scale application of baker’s yeast mediatedreductions of prochiral α,β-unsaturated aldehydes isusually hindered by discouragingly low productivities.Exploiting the recently developed synergic applicationof the in situ substrate-feeding-product-removal (SFPR)technique together with recombinant isolated enzymes(enoate reductases and alcohol dehydrogenases),it was possible to achieve a 50-fold improvement ofthe productivity of the biocatalytic enantioselectivereduction of alphabrocine to the corresponding opticallyactive bromohydrin (98% ee). The latter was thenemployed in the synthesis of the active enantiomer of theappetite suppressant drug (R)-2-benzylmorpholine.