Preparative scale Achmatowicz and aza-Achmatowicz rearrangements catalyzed by Agrocybe aegerita unspecific peroxygenase

Org Biomol Chem. 2024 Jul 31;22(30):6149-6155. doi: 10.1039/d4ob00939h.

Abstract

The unspecific peroxygenase (UPO) from Agrocybe aegerita (rAaeUPO-PaDa-I-H) is an effective and practical biocatalyst for the oxidative expansion of furfuryl alcohols/amines on a preparative scale, using the Achmatowicz and aza-Achmatowicz reaction. The high activity and stability of the enzyme, which can be produced on a large scale as an air-stable lyophilised powder, renders it a versatile and scalable biocatalyst for the preparation of synthetically valuable 6-hydroxypyranones and dihydropiperidinones. In several cases, the biotransformation out-performed the analogous chemo-catalysed process, and operates under milder and greener reaction conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agrocybe* / enzymology
  • Amines / chemistry
  • Amines / metabolism
  • Biocatalysis
  • Mixed Function Oxygenases* / chemistry
  • Mixed Function Oxygenases* / metabolism
  • Molecular Structure

Substances

  • Amines
  • Mixed Function Oxygenases
  • peroxygenase

Supplementary concepts

  • Agrocybe aegerita