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

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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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