title: Promiscuous catalysis of asymmetric Michael-type additions of linear aldehydes to β-nitrostyrene by the proline-based enzyme 4-oxalocrotonate tautomerase.
abstract: Exploiting catalytic promiscuity: The proline-based enzyme 4-oxalocrotonate tautomerase (4-OT) promiscuously catalyzes asymmetric Michael-type additions of linear aldehydes--ranging from acetaldehyde to octanal--to trans-β-nitrostyrene in aqueous solvent. The presence of 1.4 mol% of 4-OT effected formation of the anticipated γ-nitroaldehydes in fair to good yields with dr values of up to 93:7 and ee values of up to 81 %.
authors.affiliation: Department of Pharmaceutical Biology, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen, The Netherlands.
authors.forename: Yufeng
authors.initials: Y
authors.lastname: Miao
authors.forename: Edzard M
authors.initials: EM
authors.lastname: Geertsema
authors.forename: Pieter G
authors.initials: PG
authors.lastname: Tepper
authors.forename: Ellen
authors.initials: E
authors.lastname: Zandvoort
authors.forename: Gerrit J
authors.initials: GJ
authors.lastname: Poelarends
mesh_terms: D000447:Aldehydes / Q000737:chemistry / Q000378:metabolism*; D002384:Catalysis; D007535:Isomerases / Q000737:chemistry / Q000378:metabolism*; D008958:Models, Molecular; D011392:Proline / Q000737:chemistry / Q000378:metabolism; D013343:Styrenes / Q000737:chemistry / Q000378:metabolism*
chemical_list: D000447:Aldehydes; D013343:Styrenes; C011955:beta-nitrostyrene; D011392:Proline; C021918:4-oxalocrotonate tautomerase; D007535:Isomerases