Biocatalytic C=C Bond Reduction through Carbon Nanodot-Sensitized Regeneration of NADH Analogues

Jinhyun Kim, Sahng Ha Lee, Florian Tieves, Da Som Choi, Frank Hollmann, Caroline E. Paul*, Chan Beum Park

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

30 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)13825-13828
JournalAngewandte Chemie - International Edition
Volume57
Issue number42
Early online date30 Jul 2018
DOIs
Publication statusPublished - 15 Oct 2018

Keywords

  • alkene hydrogenation
  • asymmetric catalysis
  • carbon nanodot
  • NADH analogues
  • photobiocatalysis

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    Kim, J., Lee, S. H., Tieves, F., Choi, D. S., Hollmann, F., Paul, C. E., & Park, C. B. (2018). Biocatalytic C=C Bond Reduction through Carbon Nanodot-Sensitized Regeneration of NADH Analogues. Angewandte Chemie - International Edition, 57(42), 13825-13828. https://doi.org/10.1002/anie.201804409