Methyl-Shifted Farnesyldiphosphate Derivatives Are Substrates for Sesquiterpene Cyclases
Vanessa Harms, Benjamin Schröder, Clara Oberhauser, Cong Duc Tran, Sven Winkler, Gerald Dräger, Andreas Kirschning
Abstract
New sesquiterpene backbones are accessible after biotransformation of presilphiperfolan-8β-ol synthase (BcBOT2), a fungal sesquiterpene synthase, with non-natural farnesyldiphosphates in which methyl groups are shifted by one position toward the diphosphate terminus. One of the macrocycles formed, a new germacrene A derivative, undergoes a Cope rearrangement to iso-β-elemene. Three of the new terpenoids show olfactoric properties that range from an intense peppery note to a citrus, ozone-like, and fruity scent.
Topics & Concepts
SesquiterpeneChemistryStereochemistryDerivative (finance)TerpenoidGermacreneATP synthaseBiotransformationTerpeneOrganic chemistryEnzymeEconomicsFinancial economicsPlant biochemistry and biosynthesisMicrobial Natural Products and BiosynthesisSesquiterpenes and Asteraceae Studies