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.
|Number of pages||7|
|Journal||Beilstein Journal of Organic Chemistry|
|State||Published - 2022|
Bibliographical noteFunding 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).
© 2022 Zev et al.; licensee Beilstein-Institut.
- enzyme mechanism
- kinetic control
- quantum mechanics
- terpene synthases