biostudies-literatureGuo XSwiss National Science Foundation5052-5056https://www.ebi.ac.uk/biostudies/studies/S-EPMC5994792biostudies-literatureUnknown9(22)Visible light-driven reduction of imines to enantioenriched amines in aqueous solution is demonstrated for the first time. Excitation of a new water-soluble variant of the widely used [Ir(ppy)₃] (ppy = 2-phenylpyridine) photosensitizer in the presence of a cyclic imine affords a highly reactive α-amino alkyl radical that is intercepted by hydrogen atom transfer (HAT) from ascorbate or thiol donors to afford the corresponding amine. The enzyme monoamine oxidase (MAO-N-9) selectively catalyzes the oxidation of one of the enantiomers to the corresponding imine. Upon combining the photoredox and biocatalytic processes under continuous photo-irradiation, enantioenriched amines are obtained in excellent yields. To the best of our knowledge, this is the first demonstration of a concurrent photoredox- and enzymatic catalysis leading to a light-driven asymmetric synthesis of amines.Chemical scienceEnantioselective synthesis of amines by combining photoredox and enzymatic catalysis in a cyclic reaction network.PMC5994792NCCR Molecular Systems EngineeringOkamoto YGuo XWard TRWenger OSSchreier MRfalseEnantioselective synthesis of amines by combining photoredox and enzymatic catalysis in a cyclic reaction network.Visible light-driven reduction of imines to enantioenriched amines in aqueous solution is demonstrated for the first time. Excitation of a new water-soluble variant of the widely used [Ir(ppy)₃] (ppy = 2-phenylpyridine) photosensitizer in the presence of a cyclic imine affords a highly reactive α-amino alkyl radical that is intercepted by hydrogen atom transfer (HAT) from ascorbate or thiol donors to afford the corresponding amine. The enzyme monoamine oxidase (MAO-N-9) selectively catalyzes the oxidation of one of the enantiomers to the corresponding imine. Upon combining the photoredox and biocatalytic processes under continuous photo-irradiation, enantioenriched amines are obtained in excellent yields. To the best of our knowledge, this is the first demonstration of a concurrent photoredox- and enzymatic catalysis leading to a light-driven asymmetric synthesis of amines.2018-01-01T00:00:00Z2018 Jun2025-04-04T09:38:49.737Z2019-03-26T23:43:27ZS-EPMC59947922993803510.1039/c8sc01561a