Chemoenzymatic Total Synthesis of Sorbicatechol Structural Analogues and Evaluation of Their Antiviral Potential

Chembiochem. 2020 Feb 17;21(4):492-495. doi: 10.1002/cbic.201900472. Epub 2019 Nov 19.

Abstract

Sorbicillinoids are fungal polyketides characterized by highly complex and diverse molecular structures, with considerable stereochemical intricacy combined with a high degree of oxygenation. Many sorbicillinoids possess promising biological activities. An interesting member of this natural product family is sorbicatechol A, which is reported to have antiviral activity, particularly against influenza A virus (H1N1). Through a straightforward, one-pot chemoenzymatic approach with recently developed oxidoreductase SorbC, the characteristic bicyclo[2.2.2]octane core of sorbicatechol is structurally diversified by variation of its natural 2-methoxyphenol substituent. This facilitates the preparation of a focused library of structural analogues bearing substituted aromatic systems, alkanes, heterocycles, and ethers. Fast access to this structural diversity provides an opportunity to explore the antiviral potential of the sorbicatechol family.

Keywords: antiviral agents; biocatalysis; natural products; sorbicillinoids; total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alphainfluenzavirus / drug effects
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology
  • HIV / drug effects
  • Molecular Structure
  • Polyketides* / chemical synthesis
  • Polyketides* / chemistry

Substances

  • Antiviral Agents
  • Polyketides