PubMed: Heterocyclic and Alkyne Terpenoids by Terpene Synthase-Mediated Biotransformation of Non-Natural Prenyl Diphosphates: Access to New Fragrances and Probes

PubMed: Heterocyclic and Alkyne Terpenoids by Terpene Synthase-Mediated Biotransformation of Non-Natural Prenyl Diphosphates: Access to New Fragrances and Probes

Chembiochem. 2022 Sep 29:e202200211. doi: 10.1002/cbic.202200211. Online ahead of print.

ABSTRACT

Two terpene cyclases were used as biocatalytic tool, namely, limonene synthase from Cannabis sativa (CLS) and 5-epi-aristolochene synthase (TEAS) from Nicotiana tabacum. They showed significant substrate flexibility towards non-natural prenyl diphosphates to form novel terpenoids, including core oxa- and thia-heterocycles and alkyne-modified terpenoids. We elucidated the structures of five novel monoterpene-analogues and a known sesquiterpene-analogue. These results reflected the terpene synthases’ ability and promiscuity to broaden the pool of terpenoids with structurally complex analogues. Docking studies highlight an on-off conversion of the unnatural substrates.

PMID:36173145 | DOI:10.1002/cbic.202200211

#CBD #Hemp https://pubmed.ncbi.nlm.nih.gov/36173145/?utm_source=Chrome&utm_medium=rss&utm_campaign=pubmed-2&utm_content=1NqsX9BbHlDygQ8TcgAlJilHgPpiuKQtyIr–a3-xbLzPoB9xM&fc=20220928170152&ff=20220929162129&v=2.17.8 September 29, 2022 10:00 am

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