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Record number 541493
Title Biocatalytic C=C Bond Reduction through Carbon Nanodot-Sensitized Regeneration of NADH Analogues
Author(s) Kim, Jinhyun; Lee, Sahng Ha; Tieves, Florian; Choi, Da Som; Hollmann, Frank; Paul, Caroline E.; Park, Chan Beum
Source Angewandte Chemie-International Edition 57 (2018)42. - ISSN 1433-7851 - p. 13825 - 13828.
DOI https://doi.org/10.1002/anie.201804409
Department(s) Laboratory for Organic Chemistry
Publication type Refereed Article in a scientific journal
Publication year 2018
Keyword(s) alkene hydrogenation - asymmetric catalysis - carbon nanodot - NADH analogues - photobiocatalysis
Abstract

Light-driven activation of redox enzymes is an emerging route for sustainable chemical synthesis. Among redox enzymes, the family of Old Yellow Enzyme (OYE) dependent on the nicotinamide adenine dinucleotide cofactor (NADH) catalyzes the stereoselective reduction of α,β-unsaturated hydrocarbons. Here, we report OYE-catalyzed asymmetric hydrogenation through light-driven regeneration of NADH and its analogues (mNADHs) by N-doped carbon nanodots (N-CDs), a zero-dimensional photocatalyst. Our spectroscopic and photoelectrochemical analyses verified the transfer of photo-induced electrons from N-CDs to an organometallic electron mediator (M) for highly regioselective regeneration of cofactors. Light triggered the reduction of NAD+ and mNAD+s with the cooperation of N-CDs and M, and the reduction behaviors of cofactors were dependent on their own reduction peak potentials. The regenerated cofactors subsequently delivered hydrides to OYE for stereoselective conversions of a broad range of substrates with excellent biocatalytic efficiencies.

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