Understanding the competing pathways leading to hydropyrene and isoelisabethatriene

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) di...

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Autores principales: Zev, Shani, Ringel, Marion, Driller, Ronja, Loll, Bernhard, Brück, Thomas, Major, Dan T
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9359192/
https://www.ncbi.nlm.nih.gov/pubmed/35965858
http://dx.doi.org/10.3762/bjoc.18.97
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author Zev, Shani
Ringel, Marion
Driller, Ronja
Loll, Bernhard
Brück, Thomas
Major, Dan T
author_facet Zev, Shani
Ringel, Marion
Driller, Ronja
Loll, Bernhard
Brück, Thomas
Major, Dan T
author_sort Zev, Shani
collection PubMed
description 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.
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spelling pubmed-93591922022-08-12 Understanding the competing pathways leading to hydropyrene and isoelisabethatriene Zev, Shani Ringel, Marion Driller, Ronja Loll, Bernhard Brück, Thomas Major, Dan T Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2022-08-04 /pmc/articles/PMC9359192/ /pubmed/35965858 http://dx.doi.org/10.3762/bjoc.18.97 Text en Copyright © 2022, Zev et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Zev, Shani
Ringel, Marion
Driller, Ronja
Loll, Bernhard
Brück, Thomas
Major, Dan T
Understanding the competing pathways leading to hydropyrene and isoelisabethatriene
title Understanding the competing pathways leading to hydropyrene and isoelisabethatriene
title_full Understanding the competing pathways leading to hydropyrene and isoelisabethatriene
title_fullStr Understanding the competing pathways leading to hydropyrene and isoelisabethatriene
title_full_unstemmed Understanding the competing pathways leading to hydropyrene and isoelisabethatriene
title_short Understanding the competing pathways leading to hydropyrene and isoelisabethatriene
title_sort understanding the competing pathways leading to hydropyrene and isoelisabethatriene
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9359192/
https://www.ncbi.nlm.nih.gov/pubmed/35965858
http://dx.doi.org/10.3762/bjoc.18.97
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