Understanding the competing pathways leading to hydropyrene and isoelisabethatriene

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

Research output: Contribution to journalArticlepeer-review


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 languageEnglish
Pages (from-to)972-978
Number of pages7
JournalBeilstein Journal of Organic Chemistry
StatePublished - 2022

Bibliographical note

Funding Information:
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).

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


  • diterpenes
  • enzyme mechanism
  • kinetic control
  • quantum mechanics
  • terpene synthases
  • thermodynamic


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