Molecular Basis for Stellatic Acid Biosynthesis: A Genome Mining Approach for Discovery of Sesterterpene Synthases

Org Lett. 2015 Sep 18;17(18):4644-7. doi: 10.1021/acs.orglett.5b02404. Epub 2015 Sep 9.

Abstract

The search for a new sesterterpene synthase in the genome of Emericella variecolor, which reportedly produces diverse sesterterpenoids, is described. One gene product (a chimeric protein with prenyltransferase and terpene cyclase domains) led to the synthesis of a novel tricyclic sesterterpene, stellata-2,6,19-triene (1), from DMAPP and IPP, and the hydrocarbon was further transformed into stellatic acid (2) by cytochrome P450 monooxygenase encoded by the gene adjacent to the sesterterpene synthase gene.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkyl and Aryl Transferases / genetics
  • Alkyl and Aryl Transferases / metabolism*
  • Emericella / enzymology
  • Emericella / genetics
  • Molecular Structure
  • Sesterterpenes / chemistry*
  • Sesterterpenes / isolation & purification

Substances

  • Sesterterpenes
  • stellata-2,6,19-triene
  • stellatic acid
  • Alkyl and Aryl Transferases
  • terpene synthase