Understanding the competing pathways leading to hydropyrene and isoelisabethatriene

Shani Zev; Marion Ringel; Ronja Driller; Bernhard Loll; Thomas Brück; Dan T. Major

doi:10.3762/bjoc.18.97

Understanding the competing pathways leading to hydropyrene and isoelisabethatriene

Shani Zev, Marion Ringel, Ronja Driller, Bernhard Loll, Thomas Brück, Dan T. Major

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

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, isoelisabethatrienes A and B. Fascinatingly, a single active site mutation (M75L) diverts the product distribution towards isoelisabethatrienes 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.

Original language	English
Pages (from-to)	972-978
Number of pages	7
Journal	Beilstein Journal of Organic Chemistry
Volume	18
DOIs	https://doi.org/10.3762/bjoc.18.97
State	Published - 2022

Bibliographical note

Publisher Copyright:
© 2022 Zev et al.; licensee Beilstein-Institut.

Funding

MR and TB gratefully acknowledge funding by the Werner Siemens foundation for establishing the field of Synthetic Biotechnology at TUM. This work was supported by a grant from the Israel Science Foundation (Grant 1683/18) (DTM) and by a grant from the German-Israeli Foundation for Scientific Research and Development (Grant I-85-302.14-2018) (DTM, TB, BL).

Funders	Funder number
Werner Siemens-Stiftung
German-Israeli Foundation for Scientific Research and Development	I-85-302.14-2018
Israel Science Foundation	1683/18

Keywords

diterpenes
enzyme mechanism
kinetic control
quantum mechanics
terpene synthases
thermodynamic

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10.3762/bjoc.18.97

Cite this

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AU - Driller, Ronja

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AU - Brück, Thomas

AU - Major, Dan T.

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Understanding the competing pathways leading to hydropyrene and isoelisabethatriene

Abstract

Bibliographical note

Funding

Keywords

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