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- Title
Biocatalytic C=C Bond Reduction through Carbon Nanodot‐Sensitized Regeneration of NADH Analogues.
- Authors
Kim, Jinhyun; Lee, Sahng Ha; Tieves, Florian; Choi, Da Som; Hollmann, Frank; Paul, Caroline E.; Park, Chan Beum
- 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.
- Subjects
CARBON-carbon bonds; BIOCATALYSIS; NICOTINAMIDE adenine dinucleotide phosphate; HYDROGENATION; PHOTOSENSITIZERS
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 42, p14021
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201804409