title: Enoyl acyl carrier protein reductase (FabI) catalyzed asymmetric reduction of the C=C double bond of α,β-unsaturated ketones: preparation of (R)-2-alkyl-cyclopentanones.
abstract: Enoyl-ACP reductase (FabI) was identified as a non-OYE 'ene'-reductase for asymmetric reduction of the C=C double bond of α, β-unsaturated ketones. Reduction of several 2-alkylidenecyclopentanones with A-FabI and E-FabI gave (R)-2-alkylcyclopentanones in 95-90% and 70-81% ee, respectively. The product ee was improved to 99-98% in high yield by subsequent one-pot biooxidation.
authors.affiliation: Department of Chemical and Biomolecular Engineering, National University of Singapore, 4 Engineering Drive 4, Singapore117585. chelz@nus.edu.sg.
authors.forename: Ji
authors.initials: J
authors.lastname: Liu
authors.forename: Jinchuan
authors.initials: J
authors.lastname: Wu
authors.forename: Zhi
authors.initials: Z
authors.lastname: Li
mesh_terms: D000150:Acinetobacter / Q000201:enzymology* / Q000235:genetics; D000478:Alkylation; D003001:Cloning, Molecular; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D050753:Enoyl-(Acyl-Carrier-Protein) Reductase (NADH) / Q000235:genetics / Q000378:metabolism*; D004926:Escherichia coli / Q000201:enzymology* / Q000235:genetics; D007659:Ketones / Q000737:chemistry / Q000378:metabolism*; D008958:Models, Molecular; D062105:Molecular Docking Simulation; D010084:Oxidation-Reduction; D015202:Protein Engineering
chemical_list: D003517:Cyclopentanes; D007659:Ketones; C007201:cyclopentanone; D050753:Enoyl-(Acyl-Carrier-Protein) Reductase (NADH)