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Oxyfunctionalization of pyridine derivatives using whole cells of Burkholderia sp. MAK1

Pyridinols and pyridinamines are important intermediates with many applications in chemical industry. The pyridine derivatives are in great demand as synthons for pharmaceutical products. Moreover, pyridines are used either as biologically active substances or as building blocks for polymers with un...

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Autores principales: Stankevičiūtė, Jonita, Vaitekūnas, Justas, Petkevičius, Vytautas, Gasparavičiūtė, Renata, Tauraitė, Daiva, Meškys, Rolandas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5159870/
https://www.ncbi.nlm.nih.gov/pubmed/27982075
http://dx.doi.org/10.1038/srep39129
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author Stankevičiūtė, Jonita
Vaitekūnas, Justas
Petkevičius, Vytautas
Gasparavičiūtė, Renata
Tauraitė, Daiva
Meškys, Rolandas
author_facet Stankevičiūtė, Jonita
Vaitekūnas, Justas
Petkevičius, Vytautas
Gasparavičiūtė, Renata
Tauraitė, Daiva
Meškys, Rolandas
author_sort Stankevičiūtė, Jonita
collection PubMed
description Pyridinols and pyridinamines are important intermediates with many applications in chemical industry. The pyridine derivatives are in great demand as synthons for pharmaceutical products. Moreover, pyridines are used either as biologically active substances or as building blocks for polymers with unique physical properties. Application of enzymes or whole cells is an attractive strategy for preparation of hydroxylated pyridines since the methods for chemical synthesis of pyridinols, particularly aminopyridinols, are usually limited or inefficient. Burkholderia sp. MAK1 (DSM102049), capable of using pyridin-2-ol as the sole carbon and energy source, was isolated from soil. Whole cells of Burkholderia sp. MAK1 were confirmed to possess a good ability to convert different pyridin-2-amines and pyridin-2-ones into their 5-hydroxy derivatives. Moreover, several methylpyridines as well as methylated pyrazines were converted to appropriate N-oxides. In conclusion, regioselective oxyfunctionalization of pyridine derivatives using whole cells of Burkholderia sp. MAK1 is a promising method for the preparation of various pyridin-5-ols and pyridin-N-oxides.
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spelling pubmed-51598702016-12-21 Oxyfunctionalization of pyridine derivatives using whole cells of Burkholderia sp. MAK1 Stankevičiūtė, Jonita Vaitekūnas, Justas Petkevičius, Vytautas Gasparavičiūtė, Renata Tauraitė, Daiva Meškys, Rolandas Sci Rep Article Pyridinols and pyridinamines are important intermediates with many applications in chemical industry. The pyridine derivatives are in great demand as synthons for pharmaceutical products. Moreover, pyridines are used either as biologically active substances or as building blocks for polymers with unique physical properties. Application of enzymes or whole cells is an attractive strategy for preparation of hydroxylated pyridines since the methods for chemical synthesis of pyridinols, particularly aminopyridinols, are usually limited or inefficient. Burkholderia sp. MAK1 (DSM102049), capable of using pyridin-2-ol as the sole carbon and energy source, was isolated from soil. Whole cells of Burkholderia sp. MAK1 were confirmed to possess a good ability to convert different pyridin-2-amines and pyridin-2-ones into their 5-hydroxy derivatives. Moreover, several methylpyridines as well as methylated pyrazines were converted to appropriate N-oxides. In conclusion, regioselective oxyfunctionalization of pyridine derivatives using whole cells of Burkholderia sp. MAK1 is a promising method for the preparation of various pyridin-5-ols and pyridin-N-oxides. Nature Publishing Group 2016-12-16 /pmc/articles/PMC5159870/ /pubmed/27982075 http://dx.doi.org/10.1038/srep39129 Text en Copyright © 2016, The Author(s) http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Stankevičiūtė, Jonita
Vaitekūnas, Justas
Petkevičius, Vytautas
Gasparavičiūtė, Renata
Tauraitė, Daiva
Meškys, Rolandas
Oxyfunctionalization of pyridine derivatives using whole cells of Burkholderia sp. MAK1
title Oxyfunctionalization of pyridine derivatives using whole cells of Burkholderia sp. MAK1
title_full Oxyfunctionalization of pyridine derivatives using whole cells of Burkholderia sp. MAK1
title_fullStr Oxyfunctionalization of pyridine derivatives using whole cells of Burkholderia sp. MAK1
title_full_unstemmed Oxyfunctionalization of pyridine derivatives using whole cells of Burkholderia sp. MAK1
title_short Oxyfunctionalization of pyridine derivatives using whole cells of Burkholderia sp. MAK1
title_sort oxyfunctionalization of pyridine derivatives using whole cells of burkholderia sp. mak1
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5159870/
https://www.ncbi.nlm.nih.gov/pubmed/27982075
http://dx.doi.org/10.1038/srep39129
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