A detailed view on 1,8-cineol biosynthesis by Streptomyces clavuligerus

The stereochemical course of the cyclisation reaction catalysed by the bacterial 1,8-cineol synthase from Streptomyces clavuligerus was investigated using stereospecifically deuterated substrates. In contrast to the well investigated plant enzyme from Salvia officinalis, the reaction proceeds via (S...

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Detalles Bibliográficos
Autores principales: Rinkel, Jan, Rabe, Patrick, zur Horst, Laura, Dickschat, Jeroen S
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238540/
https://www.ncbi.nlm.nih.gov/pubmed/28144299
http://dx.doi.org/10.3762/bjoc.12.225
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author Rinkel, Jan
Rabe, Patrick
zur Horst, Laura
Dickschat, Jeroen S
author_facet Rinkel, Jan
Rabe, Patrick
zur Horst, Laura
Dickschat, Jeroen S
author_sort Rinkel, Jan
collection PubMed
description The stereochemical course of the cyclisation reaction catalysed by the bacterial 1,8-cineol synthase from Streptomyces clavuligerus was investigated using stereospecifically deuterated substrates. In contrast to the well investigated plant enzyme from Salvia officinalis, the reaction proceeds via (S)-linalyl diphosphate and the (S)-terpinyl cation, while the final cyclisation reaction is in both cases a syn addition, as could be shown by incubation of (2-(13)C)geranyl diphosphate in deuterium oxide.
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spelling pubmed-52385402017-01-31 A detailed view on 1,8-cineol biosynthesis by Streptomyces clavuligerus Rinkel, Jan Rabe, Patrick zur Horst, Laura Dickschat, Jeroen S Beilstein J Org Chem Full Research Paper The stereochemical course of the cyclisation reaction catalysed by the bacterial 1,8-cineol synthase from Streptomyces clavuligerus was investigated using stereospecifically deuterated substrates. In contrast to the well investigated plant enzyme from Salvia officinalis, the reaction proceeds via (S)-linalyl diphosphate and the (S)-terpinyl cation, while the final cyclisation reaction is in both cases a syn addition, as could be shown by incubation of (2-(13)C)geranyl diphosphate in deuterium oxide. Beilstein-Institut 2016-11-04 /pmc/articles/PMC5238540/ /pubmed/28144299 http://dx.doi.org/10.3762/bjoc.12.225 Text en Copyright © 2016, Rinkel et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Rinkel, Jan
Rabe, Patrick
zur Horst, Laura
Dickschat, Jeroen S
A detailed view on 1,8-cineol biosynthesis by Streptomyces clavuligerus
title A detailed view on 1,8-cineol biosynthesis by Streptomyces clavuligerus
title_full A detailed view on 1,8-cineol biosynthesis by Streptomyces clavuligerus
title_fullStr A detailed view on 1,8-cineol biosynthesis by Streptomyces clavuligerus
title_full_unstemmed A detailed view on 1,8-cineol biosynthesis by Streptomyces clavuligerus
title_short A detailed view on 1,8-cineol biosynthesis by Streptomyces clavuligerus
title_sort detailed view on 1,8-cineol biosynthesis by streptomyces clavuligerus
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238540/
https://www.ncbi.nlm.nih.gov/pubmed/28144299
http://dx.doi.org/10.3762/bjoc.12.225
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