title: Biocatalytic Michael-type additions of acetaldehyde to nitroolefins with the proline-based enzyme 4-oxalocrotonate tautomerase yielding enantioenriched γ-nitroaldehydes.
abstract: Call me Michaelase: The enzyme 4-oxalocrotonate tautomerase (4-OT) promiscuously catalyzes the Michael-type addition of acetaldehyde to a collection of aromatic and aliphatic nitroolefins with high stereoselectivity producing precursors of γ-aminobutyric acid (GABA) analogues.
authors.affiliation: Department of Pharmaceutical Biology, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen (The Netherlands).
authors.forename: Edzard M
authors.initials: EM
authors.lastname: Geertsema
authors.forename: Yufeng
authors.initials: Y
authors.lastname: Miao
authors.forename: Pieter G
authors.initials: PG
authors.lastname: Tepper
authors.forename: Pim
authors.initials: P
authors.lastname: de Haan
authors.forename: Ellen
authors.initials: E
authors.lastname: Zandvoort
authors.forename: Gerrit J
authors.initials: GJ
authors.lastname: Poelarends
mesh_terms: D000079:Acetaldehyde / Q000737:chemistry / Q000378:metabolism*; D000475:Alkenes / Q000737:chemistry / Q000378:metabolism*; D055162:Biocatalysis; D002244:Carbon / Q000737:chemistry; D007535:Isomerases / Q000378:metabolism*; D009574:Nitro Compounds / Q000737:chemistry*; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism; D005680:gamma-Aminobutyric Acid / Q000378:metabolism
chemical_list: D000475:Alkenes; D009574:Nitro Compounds; D005680:gamma-Aminobutyric Acid; D002244:Carbon; D011392:Proline; C021918:4-oxalocrotonate tautomerase; D007535:Isomerases; D000079:Acetaldehyde
keywords: C-C bond formation; Michael-type addition; aminobutyric acid; biocatalysis; enzymes