A Simple Screening and Optimization Bioprocess for Long-Chain Peptide Catalysts Applied to Asymmetric Aldol Reaction

Molecules. 2023 Oct 9;28(19):6985. doi: 10.3390/molecules28196985.

Abstract

Peptides have demonstrated their efficacy as catalysts in asymmetric aldol reactions. But the constraints inherent in chemical synthesis have imposed limitations on the viability of long-chain peptide catalysts. A noticeable dearth of tools has impeded the swift and effective screening of peptide catalysts using biological methods. To address this, we introduce a straightforward bioprocess for the screening of peptide catalysts for asymmetric aldol reactions. We synthesized several peptides through this method and obtained a 15-amino acid peptide. This peptide exhibited asymmetric aldol catalytic activity, achieving 77% ee in DMSO solvent and 63% ee with over an 80.8% yield in DMSO mixed with a pH 9.0 buffer solution. The successful application of our innovative approach not only represents an advancement but also paves the way for currently unexplored research avenues.

Keywords: asymmetric aldol reaction; fusion protein; peptide catalysis; simple bioprocess.

MeSH terms

  • Aldehydes / chemistry
  • Catalysis
  • Dimethyl Sulfoxide*
  • Peptides* / chemistry
  • Solvents / chemistry
  • Stereoisomerism

Substances

  • 3-hydroxybutanal
  • Dimethyl Sulfoxide
  • Peptides
  • Aldehydes
  • Solvents