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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...

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Autores principales: Żądło‐Dobrowolska, Anna, Schmidt, Nina G., Kroutil, Wolfgang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
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.
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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
title_full Thioesters as Acyl Donors in Biocatalytic Friedel‐Crafts‐type Acylation Catalyzed by Acyltransferase from Pseudomonas Protegens
title_fullStr Thioesters as Acyl Donors in Biocatalytic Friedel‐Crafts‐type Acylation Catalyzed by Acyltransferase from Pseudomonas Protegens
title_full_unstemmed Thioesters as Acyl Donors in Biocatalytic Friedel‐Crafts‐type Acylation Catalyzed by Acyltransferase from Pseudomonas Protegens
title_short Thioesters as Acyl Donors in Biocatalytic Friedel‐Crafts‐type Acylation Catalyzed by Acyltransferase from Pseudomonas Protegens
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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