The substrate flexibility of eight purified sesquiterpene cyclases was evaluated using six new heteroatom-modified farnesyl pyrophosphates, and the formation of six new heteroatom-modified macrocyclic and tricyclic sesquiterpenoids is described. GC-O analysis revealed that tricyclic tetrahydrofuran exhibits an ethereal, peppery, and camphor-like olfactoric scent.
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.
Die Substratflexibilität von acht rekombinant erzeugten Sesquiterpencyclasen wurde unter Anwendung von sechs neuen Heteroatom‐modifizierten Farnesylpyrophosphaten untersucht. Als Ergebnis werden sechs neue makro‐ oder tricyclische, Heteroatom‐modifizierte Sesquiterpene beschrieben. Die GC‐O‐Analyse zeigte, dass das tricyclische Tetrahydrofuran etherische, pfeffrige und campherartige Geruchsnoten aufweist.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.