Oxepin Formation in Fungi Implies Specific and Stereoselective Ring Expansion

Org Lett. 2021 Mar 19;23(6):2024-2028. doi: 10.1021/acs.orglett.1c00166. Epub 2021 Mar 3.

Abstract

Oxepinamides are fungal oxepine-pyrimidinone-ketopiperazine derivatives. In this study, we elucidated the biosynthetic pathway of oxepinamide D in Aspergillus ustus by gene deletion, heterologous expression, feeding experiments, and enzyme assays. We demonstrated that the cytochrome P450 enzymes catalyzed highly specific and stereoselective oxepin ring formation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspergillus / chemistry
  • Aspergillus / metabolism*
  • Biosynthetic Pathways
  • Catalysis
  • Cytochrome P-450 Enzyme System / chemistry*
  • Cytochrome P-450 Enzyme System / metabolism
  • Enzyme Assays
  • Fungi / chemistry*
  • Fungi / metabolism
  • Molecular Structure
  • Oxepins / chemistry*

Substances

  • Oxepins
  • Cytochrome P-450 Enzyme System

Supplementary concepts

  • Aspergillus ustus