title: Oxygenase-catalyzed desymmetrization of N,N-dialkyl-piperidine-4-carboxylic acids.
abstract: γ-Butyrobetaine hydroxylase (BBOX) is a 2-oxoglutarate dependent oxygenase that catalyzes the final hydroxylation step in the biosynthesis of carnitine. BBOX was shown to catalyze the oxidative desymmetrization of achiral N,N-dialkyl piperidine-4-carboxylates to give products with two or three stereogenic centers.
authors.affiliation: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA (UK).
authors.forename: Anna M
authors.initials: AM
authors.lastname: Rydzik
authors.forename: Ivanhoe K H
authors.initials: IK
authors.lastname: Leung
authors.forename: Grazyna T
authors.initials: GT
authors.lastname: Kochan
authors.forename: Michael A
authors.initials: MA
authors.lastname: McDonough
authors.forename: Timothy D W
authors.initials: TD
authors.lastname: Claridge
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Schofield
mesh_terms: D055162:Biocatalysis; D002264:Carboxylic Acids / Q000737:chemistry / Q000378:metabolism*; D002331:Carnitine / Q000096:biosynthesis / Q000737:chemistry; D020134:Catalytic Domain; D010084:Oxidation-Reduction; D010880:Piperidines / Q000737:chemistry; D013237:Stereoisomerism; D050563:gamma-Butyrobetaine Dioxygenase / Q000737:chemistry / Q000378:metabolism*
chemical_list: D002264:Carboxylic Acids; D010880:Piperidines; C032727:piperidine; D050563:gamma-Butyrobetaine Dioxygenase; D002331:Carnitine
keywords: C-H activation; biocatalysis; desymmetrisation; oxygenases; γ-butyrobetaine hydroxylase