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

doi: 10.1002/cbic.202200211.

Online ahead of print.

Benjamin Weigel¹, Jeanette Ludwig¹, Roman A Weber¹, Steve Ludwig¹, Claudia Lennicke¹, Paul Schrank¹, Mehdi D Davari¹, Mohamed Nagia^1 2, Ludger A Wessjohann¹

Affiliations

PMID: 36173145
DOI: 10.1002/cbic.202200211

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.

Keywords: biotransformation, medium-sized rings, molecular docking, terpene synthases, unnatural terpenoids

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References

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

Abstract

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