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Thioesters as Acyl Donors in Biocatalytic Friedel‐Crafts‐type Acylation Catalyzed by Acyltransferase from Pseudomonas Protegens
Functionalization of aromatic compounds by acylation has considerable significance in synthetic organic chemistry. As an alternative to chemical Friedel‐Crafts acylation, the C‐acyltransferase from Pseudomonas protegens has been found to catalyze C−C bond formation with non‐natural resorcinol substr...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6686624/ https://www.ncbi.nlm.nih.gov/pubmed/31423289 http://dx.doi.org/10.1002/cctc.201801856 |
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author | Żądło‐Dobrowolska, Anna Schmidt, Nina G. Kroutil, Wolfgang |
author_facet | Żądło‐Dobrowolska, Anna Schmidt, Nina G. Kroutil, Wolfgang |
author_sort | Żądło‐Dobrowolska, Anna |
collection | PubMed |
description | Functionalization of aromatic compounds by acylation has considerable significance in synthetic organic chemistry. As an alternative to chemical Friedel‐Crafts acylation, the C‐acyltransferase from Pseudomonas protegens has been found to catalyze C−C bond formation with non‐natural resorcinol substrates. Extending the scope of acyl donors, it is now shown that the enzyme is also able to catalyze C−S bond cleavage prior to C−C bond formation, thus aliphatic and aromatic thioesters can be used as acyl donors. It is worth to mention that this reaction can be performed in aqueous buffer. Identifying ethyl thioacetate as the most suitable acetyl donor, the products were obtained with up to >99 % conversion and up to 88 % isolated yield without using additional base additives; this represents a significant advancement to prior protocols. |
format | Online Article Text |
id | pubmed-6686624 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-66866242019-08-14 Thioesters as Acyl Donors in Biocatalytic Friedel‐Crafts‐type Acylation Catalyzed by Acyltransferase from Pseudomonas Protegens Żądło‐Dobrowolska, Anna Schmidt, Nina G. Kroutil, Wolfgang ChemCatChem Full Papers Functionalization of aromatic compounds by acylation has considerable significance in synthetic organic chemistry. As an alternative to chemical Friedel‐Crafts acylation, the C‐acyltransferase from Pseudomonas protegens has been found to catalyze C−C bond formation with non‐natural resorcinol substrates. Extending the scope of acyl donors, it is now shown that the enzyme is also able to catalyze C−S bond cleavage prior to C−C bond formation, thus aliphatic and aromatic thioesters can be used as acyl donors. It is worth to mention that this reaction can be performed in aqueous buffer. Identifying ethyl thioacetate as the most suitable acetyl donor, the products were obtained with up to >99 % conversion and up to 88 % isolated yield without using additional base additives; this represents a significant advancement to prior protocols. John Wiley and Sons Inc. 2019-01-09 2019-02-06 /pmc/articles/PMC6686624/ /pubmed/31423289 http://dx.doi.org/10.1002/cctc.201801856 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 | Full Papers Żądło‐Dobrowolska, Anna Schmidt, Nina G. Kroutil, Wolfgang Thioesters as Acyl Donors in Biocatalytic Friedel‐Crafts‐type Acylation Catalyzed by Acyltransferase from Pseudomonas Protegens |
title | Thioesters as Acyl Donors in Biocatalytic Friedel‐Crafts‐type Acylation Catalyzed by Acyltransferase from Pseudomonas Protegens
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title_full | Thioesters as Acyl Donors in Biocatalytic Friedel‐Crafts‐type Acylation Catalyzed by Acyltransferase from Pseudomonas Protegens
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title_fullStr | Thioesters as Acyl Donors in Biocatalytic Friedel‐Crafts‐type Acylation Catalyzed by Acyltransferase from Pseudomonas Protegens
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title_full_unstemmed | Thioesters as Acyl Donors in Biocatalytic Friedel‐Crafts‐type Acylation Catalyzed by Acyltransferase from Pseudomonas Protegens
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title_short | Thioesters as Acyl Donors in Biocatalytic Friedel‐Crafts‐type Acylation Catalyzed by Acyltransferase from Pseudomonas Protegens
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title_sort | thioesters as acyl donors in biocatalytic friedel‐crafts‐type acylation catalyzed by acyltransferase from pseudomonas protegens |
topic | Full Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6686624/ https://www.ncbi.nlm.nih.gov/pubmed/31423289 http://dx.doi.org/10.1002/cctc.201801856 |
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