[Enzymatic MBH reaction catalyzed by an artificial enzyme designed with the introduction of an unnatural tertiary amine cofactor]

Sheng Wu Gong Cheng Xue Bao. 2025 Jan 25;41(1):376-384. doi: 10.13345/j.cjb.240223.
[Article in Chinese]

Abstract

As the chip of synthetic biology, enzymes play a vital role in the bio-manufacturing industry. The development of diverse functional enzymes can provide a rich toolbox for the development of synthetic biology. This article reports the construction of an artificial enzyme with the introduction of a non-natural cofactor. By introducing the 4-dimethylaminopyridine (DMAP) cofactor into the optimal protein skeleton via covalent bonds based on a click-chemistry strategy, we successfully constructed a novel artificial enzyme with the DMAP cofactor as the catalytic center. The artificial enzyme successfully catalyzed an unnatural asymmetric Morita-Baylis- Hillman (MBH) reaction between cycloketenone and p-nitrobenzaldehyde, with a conversion rate of 90% and enantioselectivity (e.e.) of 38%. This study not only provides an effective strategy for the design of new artificial enzymes but also establishes a theoretical basis for the development of unnatural biocatalytic MBH reactions.

Keywords: Morita-Baylis-Hillman (MBH) reaction; artificial enzyme; asymmetric catalysis; biocatalysis; genetic codon expansion.

Publication types

  • English Abstract

MeSH terms

  • 4-Aminopyridine / analogs & derivatives
  • 4-Aminopyridine / chemistry
  • Amines / chemistry
  • Amines / metabolism
  • Benzaldehydes* / chemistry
  • Benzaldehydes* / metabolism
  • Biocatalysis
  • Catalysis
  • Click Chemistry
  • Coenzymes / chemistry
  • Coenzymes / metabolism
  • Enzymes / chemistry
  • Enzymes / metabolism
  • Ketones / chemistry
  • Ketones / metabolism
  • Protein Engineering
  • Stereoisomerism
  • Synthetic Biology

Substances

  • Benzaldehydes
  • 4-dimethylaminopyridine
  • 4-Aminopyridine
  • 4-nitrobenzaldehyde
  • Amines
  • Coenzymes
  • Enzymes
  • Ketones