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 journalArticleScientificpeer-review

46 Citations (Scopus)
37 Downloads (Pure)

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
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
DOIs
Publication statusPublished - 2018

Bibliographical note

Green Open Access added to TU Delft Institutional Repository ‘You share, we take care!’ – Taverne project https://www.openaccess.nl/en/you-share-we-take-care Otherwise as indicated in the copyright section: the publisher is the copyright holder of this work and the author uses the Dutch legislation to make this work public.

Keywords

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

Fingerprint

Dive into the research topics of 'Biocatalytic C=C Bond Reduction through Carbon Nanodot-Sensitized Regeneration of NADH Analogues'. Together they form a unique fingerprint.

Cite this