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Understanding the competing pathways leading to hydropyrene and isoelisabethatriene
Publikation: Bidrag til tidsskrift/Konferencebidrag i tidsskrift /Bidrag til avis › Tidsskriftartikel › Forskning › peer review
DOI
- https://doi.org/10.3762/bjoc.18.97
Forlagets udgivne version
- Shani Zev, Bar-Ilan University ,
- Marion Ringel, Technical University of Munich ,
- Ronja Driller
- Bernhard Loll, Free University of Berlin ,
- Thomas Brück, Technical University of Munich ,
- Dan T. Major, Bar-Ilan University
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.
| Originalsprog | Engelsk |
|---|---|
| Tidsskrift | Beilstein Journal of Organic Chemistry |
| Vol/bind | 18 |
| Sider (fra-til) | 972-978 |
| Antal sider | 7 |
| ISSN | 2195-951X |
| DOI | |
| Status | Udgivet - aug. 2022 |
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