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Regioselectivity of Cobalamin‐Dependent Methyltransferase Can Be Tuned by Reaction Conditions and Substrate

Regioselective reactions represent a significant challenge for organic chemistry. Here the regioselective methylation of a single hydroxy group of 4‐substituted catechols was investigated employing the cobalamin‐dependent methyltransferase from Desulfitobacterium hafniense. Catechols substituted in...

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Autores principales: Pompei, Simona, Grimm, Christopher, Farnberger, Judith E., Schober, Lukas, Kroutil, Wolfgang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7783988/
https://www.ncbi.nlm.nih.gov/pubmed/33442427
http://dx.doi.org/10.1002/cctc.202001296
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author Pompei, Simona
Grimm, Christopher
Farnberger, Judith E.
Schober, Lukas
Kroutil, Wolfgang
author_facet Pompei, Simona
Grimm, Christopher
Farnberger, Judith E.
Schober, Lukas
Kroutil, Wolfgang
author_sort Pompei, Simona
collection PubMed
description Regioselective reactions represent a significant challenge for organic chemistry. Here the regioselective methylation of a single hydroxy group of 4‐substituted catechols was investigated employing the cobalamin‐dependent methyltransferase from Desulfitobacterium hafniense. Catechols substituted in position four were methylated either in meta‐ or para‐position to the substituent depending whether the substituent was polar or apolar. While the biocatalytic cobalamin dependent methylation was meta‐selective with 4‐substituted catechols bearing hydrophilic groups, it was para‐selective for hydrophobic substituents. Furthermore, the presence of water miscible co‐solvents had a clear improving influence, whereby THF turned out to enable the formation of a single regioisomer in selected cases. Finally, it was found that also the pH led to an enhancement of regioselectivity for the cases investigated.
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spelling pubmed-77839882021-01-11 Regioselectivity of Cobalamin‐Dependent Methyltransferase Can Be Tuned by Reaction Conditions and Substrate Pompei, Simona Grimm, Christopher Farnberger, Judith E. Schober, Lukas Kroutil, Wolfgang ChemCatChem Full Papers Regioselective reactions represent a significant challenge for organic chemistry. Here the regioselective methylation of a single hydroxy group of 4‐substituted catechols was investigated employing the cobalamin‐dependent methyltransferase from Desulfitobacterium hafniense. Catechols substituted in position four were methylated either in meta‐ or para‐position to the substituent depending whether the substituent was polar or apolar. While the biocatalytic cobalamin dependent methylation was meta‐selective with 4‐substituted catechols bearing hydrophilic groups, it was para‐selective for hydrophobic substituents. Furthermore, the presence of water miscible co‐solvents had a clear improving influence, whereby THF turned out to enable the formation of a single regioisomer in selected cases. Finally, it was found that also the pH led to an enhancement of regioselectivity for the cases investigated. John Wiley and Sons Inc. 2020-10-01 2020-12-04 /pmc/articles/PMC7783988/ /pubmed/33442427 http://dx.doi.org/10.1002/cctc.202001296 Text en © 2020 The Authors. Published by Wiley-VCH GmbH 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 Full Papers
Pompei, Simona
Grimm, Christopher
Farnberger, Judith E.
Schober, Lukas
Kroutil, Wolfgang
Regioselectivity of Cobalamin‐Dependent Methyltransferase Can Be Tuned by Reaction Conditions and Substrate
title Regioselectivity of Cobalamin‐Dependent Methyltransferase Can Be Tuned by Reaction Conditions and Substrate
title_full Regioselectivity of Cobalamin‐Dependent Methyltransferase Can Be Tuned by Reaction Conditions and Substrate
title_fullStr Regioselectivity of Cobalamin‐Dependent Methyltransferase Can Be Tuned by Reaction Conditions and Substrate
title_full_unstemmed Regioselectivity of Cobalamin‐Dependent Methyltransferase Can Be Tuned by Reaction Conditions and Substrate
title_short Regioselectivity of Cobalamin‐Dependent Methyltransferase Can Be Tuned by Reaction Conditions and Substrate
title_sort regioselectivity of cobalamin‐dependent methyltransferase can be tuned by reaction conditions and substrate
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7783988/
https://www.ncbi.nlm.nih.gov/pubmed/33442427
http://dx.doi.org/10.1002/cctc.202001296
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