A conserved mechanism affecting hydride shifting and deprotonation in the synthesis of hopane triterpenes as compositions of wax in oat

Abstract

Significance Hopanoids are a group of biologically important triterpene scaffolds found in nature, but the discovery of hopane-type triterpene synthases in plants has not been reported. We discovered two types of triterpene synthases synthesizing hopanoid skeletons from monocot and dicot plants and elucidated a mechanism involving the deprotonation at different sites by site-directed mutagenesis experiments and the quantum mechanics and molecular mechanics calculation. Our results provide a genetic element for synthesizing biologically active hopane-type triterpenoids and serve as a foundation for studying the molecular mechanisms of methyl and hydride transfer in the triterpene cyclization mechanism.