Understanding the Competing Pathways Leading to Hydropyrene and Isoelisabethatriene

Submitting author affiliation:
Department of Chemistry and Institute for Nanotechnology & Advanced Materials, Bar-Ilan University, Ramat Gan, 5290002, Israel

Beilstein Arch. 2022, 202237. https://doi.org/10.3762/bxiv.2022.37.v1

Published 27 May 2022



Terpene synthases are responsible for the biosynthesis of terpenes, the largest family of natural products. Hydropyrene synthase generates hydropyrene and hydropyrenol as its main products along with two byproducts, isoelisabethatriene A and B. Fascinatingly, a single active site mutation (M75L) diverts the product distribution towards isoelisabethatriene A and B. In the current work, we study the competing pathways leading to these products using quantum chemical calculations in the gas-phase. We show that there is a great thermodynamic preference for hydropyrene and hydropyrenol formation, and hence most likely in the synthesis of the isoelisabethatriene products kinetic control is at play.  

Keywords: Diterpenes; quantum mechanics; enzyme mechanism; thermodynamic and kinetic control; terpene synthases

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Zev, S.; Ringel, M.; Driller, R.; Loll, B.; Brück, T.; Major, D. T. Beilstein Arch. 2022, 202237. doi:10.3762/bxiv.2022.37.v1

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