A Family of Related Fungal and Bacterial Di‐ and Sesterterpenes: Studies on Fusaterpenol and Variediene

The absolute configuration of fusaterpenol (GJ1012E) has been revised by an enantioselective deuteration strategy. A bifunctional enzyme with a terpene synthase and a prenyltransferase domain from Aspergillus brasiliensis was characterised as variediene synthase, and the absolute configuration of it...

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Autores principales: Rinkel, Jan, Steiner, Simon T., Bian, Guangkai, Chen, Rong, Liu, Tiangang, Dickschat, Jeroen S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7065159/
https://www.ncbi.nlm.nih.gov/pubmed/31476106
http://dx.doi.org/10.1002/cbic.201900462
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author Rinkel, Jan
Steiner, Simon T.
Bian, Guangkai
Chen, Rong
Liu, Tiangang
Dickschat, Jeroen S.
author_facet Rinkel, Jan
Steiner, Simon T.
Bian, Guangkai
Chen, Rong
Liu, Tiangang
Dickschat, Jeroen S.
author_sort Rinkel, Jan
collection PubMed
description The absolute configuration of fusaterpenol (GJ1012E) has been revised by an enantioselective deuteration strategy. A bifunctional enzyme with a terpene synthase and a prenyltransferase domain from Aspergillus brasiliensis was characterised as variediene synthase, and the absolute configuration of its product was elucidated. The uniform absolute configurations of these and structurally related di‐ and sesterterpenes together with a common stereochemical course for the geminal methyl groups of GGPP unravel a similar conformational fold of the substrate in the active sites of the terpene synthases. For variediene, a thermal reaction observed during GC/MS analysis was studied in detail for which a surprising mechanism was uncovered.
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spelling pubmed-70651592020-03-16 A Family of Related Fungal and Bacterial Di‐ and Sesterterpenes: Studies on Fusaterpenol and Variediene Rinkel, Jan Steiner, Simon T. Bian, Guangkai Chen, Rong Liu, Tiangang Dickschat, Jeroen S. Chembiochem Communications The absolute configuration of fusaterpenol (GJ1012E) has been revised by an enantioselective deuteration strategy. A bifunctional enzyme with a terpene synthase and a prenyltransferase domain from Aspergillus brasiliensis was characterised as variediene synthase, and the absolute configuration of its product was elucidated. The uniform absolute configurations of these and structurally related di‐ and sesterterpenes together with a common stereochemical course for the geminal methyl groups of GGPP unravel a similar conformational fold of the substrate in the active sites of the terpene synthases. For variediene, a thermal reaction observed during GC/MS analysis was studied in detail for which a surprising mechanism was uncovered. John Wiley and Sons Inc. 2019-11-07 2020-02-17 /pmc/articles/PMC7065159/ /pubmed/31476106 http://dx.doi.org/10.1002/cbic.201900462 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Rinkel, Jan
Steiner, Simon T.
Bian, Guangkai
Chen, Rong
Liu, Tiangang
Dickschat, Jeroen S.
A Family of Related Fungal and Bacterial Di‐ and Sesterterpenes: Studies on Fusaterpenol and Variediene
title A Family of Related Fungal and Bacterial Di‐ and Sesterterpenes: Studies on Fusaterpenol and Variediene
title_full A Family of Related Fungal and Bacterial Di‐ and Sesterterpenes: Studies on Fusaterpenol and Variediene
title_fullStr A Family of Related Fungal and Bacterial Di‐ and Sesterterpenes: Studies on Fusaterpenol and Variediene
title_full_unstemmed A Family of Related Fungal and Bacterial Di‐ and Sesterterpenes: Studies on Fusaterpenol and Variediene
title_short A Family of Related Fungal and Bacterial Di‐ and Sesterterpenes: Studies on Fusaterpenol and Variediene
title_sort family of related fungal and bacterial di‐ and sesterterpenes: studies on fusaterpenol and variediene
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7065159/
https://www.ncbi.nlm.nih.gov/pubmed/31476106
http://dx.doi.org/10.1002/cbic.201900462
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