Reserving Electrons in Cofactor Decorated Coordination Capsules for Biomimetic Electrosynthesis of α-Hydroxy/amino Esters

J Am Chem Soc. 2024 Oct 30;146(43):29272-29277. doi: 10.1021/jacs.4c08547. Epub 2024 Sep 24.

Abstract

Sustainable electricity-to-chemical conversion via the utilization of artificial catalysts inspired by redox biological systems holds great significance for catalyzing synthesis. Herein, we develop a biomimetic electrosynthesis strategy mediated by a nicotinamide adenine dinucleotide (NADH) mimic-containing coordination capsule for efficiently producing α-hydroxy/amino esters. The coordination saturated metal centers worked as an electron relay to consecutively accept single electrons while donating two electrons to the NAD+ mimics simultaneously. The protonation of the intermediate generated active NADH mimics for biomimetic hydrogenation of the substrates via the conventional enzymatic manifold with or without the presence of natural enzymes. The pocket of the capsule encapsulated the substrate and enforced the close proximity between the substrate and the NADH mimics, forming a preorganized intermediate to shift the redox potential by 0.4 V anodically. The cobalt capsule gave methyl mandelate over a range of applied potentials, with an improved yield of 92% when operated at -1.2 V compared to that of Hantzsch ester or natural NADH. Kinetic experiments revealed a Michaelis-Menten mechanism with a Km of 7.5 mM and a Kcat of 1.1 × 10-2 s-1. This extended strategy in tandem with an enzyme exhibited a TON of 650 molE-1 with an initial TOF of 185 molE-1·h-1, outperforming relevant Rh-mediated enzymatic electrosynthesis systems and providing an attractive avenue toward advanced artificial electrosynthesis.

MeSH terms

  • Biomimetic Materials / chemical synthesis
  • Biomimetic Materials / chemistry
  • Biomimetic Materials / metabolism
  • Biomimetics
  • Coordination Complexes / chemistry
  • Electrochemical Techniques
  • Electrons*
  • Esters* / chemistry
  • Molecular Structure
  • NAD* / chemistry
  • NAD* / metabolism
  • Oxidation-Reduction

Substances

  • Esters
  • NAD
  • Coordination Complexes