On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of ( S )-Ibuprofen

In this paper, we describe the effectiveness of the combination between an organic solvent system mixture with orthoformates with different chain sizes from one to four carbon atoms. These orthoesters have been used as a “water trapper/alcohol releaser molecule” to reach a notable improvement in ena...

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Published in:Catalysts
Main Authors: Oussama Khiari, Nassima Bouzemi, José María Sánchez-Montero, Andrés R. Alcántara
Format: Article in Journal/Newspaper
Language:English
Published: MDPI AG 2023
Subjects:
kinetic resolution
ibuprofen
eutomer
lipase
irreversible esterification
orthoformates
Chemical technology
TP1-1185
Chemistry
QD1-999
Antarc*
Antarctica
Online Access:https://doi.org/10.3390/catal13020251
https://doaj.org/article/7963b5455ba144ab84b062a01601b1b0
id ftdoajarticles:oai:doaj.org/article:7963b5455ba144ab84b062a01601b1b0
record_format openpolar
spelling ftdoajarticles:oai:doaj.org/article:7963b5455ba144ab84b062a01601b1b0 2024-11-03T14:50:27+00:00 On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of ( S )-Ibuprofen Oussama Khiari Nassima Bouzemi José María Sánchez-Montero Andrés R. Alcántara 2023-01-01T00:00:00Z https://doi.org/10.3390/catal13020251 https://doaj.org/article/7963b5455ba144ab84b062a01601b1b0 EN eng MDPI AG https://www.mdpi.com/2073-4344/13/2/251 https://doaj.org/toc/2073-4344 doi:10.3390/catal13020251 https://doaj.org/article/7963b5455ba144ab84b062a01601b1b0 Catalysts, Vol 13, Iss 2, p 251 (2023) kinetic resolution ibuprofen eutomer lipase irreversible esterification orthoformates Chemical technology TP1-1185 Chemistry QD1-999 article 2023 ftdoajarticles https://doi.org/10.3390/catal13020251 2024-10-09T17:27:42Z In this paper, we describe the effectiveness of the combination between an organic solvent system mixture with orthoformates with different chain sizes from one to four carbon atoms. These orthoesters have been used as a “water trapper/alcohol releaser molecule” to reach a notable improvement in enantioselectivity and enantiomeric excess of our target compound, ( S )-2-(4-isobutylphenyl)propanoic acid (ibuprofen eutomer), during the enzymatic kinetic resolution of rac -ibuprofen using immobilized lipase B of Candida antarctica as a biocatalyst. At the same time, one of the great problems of biocatalysis in organic media has been solved by eliminating excess water in the medium that allows the reversibility of the reaction. Following the optimization of the reaction conditions, an increase in enantiomeric excess and enantioselectivity was reached by using these acyl donors in the presence of a cosolvent. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Catalysts 13 2 251
institution Open Polar
collection Directory of Open Access Journals: DOAJ Articles
op_collection_id ftdoajarticles
language English
topic kinetic resolution
ibuprofen
eutomer
lipase
irreversible esterification
orthoformates
Chemical technology
TP1-1185
Chemistry
QD1-999
spellingShingle kinetic resolution
ibuprofen
eutomer
lipase
irreversible esterification
orthoformates
Chemical technology
TP1-1185
Chemistry
QD1-999
Oussama Khiari
Nassima Bouzemi
José María Sánchez-Montero
Andrés R. Alcántara
On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of ( S )-Ibuprofen
topic_facet kinetic resolution
ibuprofen
eutomer
lipase
irreversible esterification
orthoformates
Chemical technology
TP1-1185
Chemistry
QD1-999
description In this paper, we describe the effectiveness of the combination between an organic solvent system mixture with orthoformates with different chain sizes from one to four carbon atoms. These orthoesters have been used as a “water trapper/alcohol releaser molecule” to reach a notable improvement in enantioselectivity and enantiomeric excess of our target compound, ( S )-2-(4-isobutylphenyl)propanoic acid (ibuprofen eutomer), during the enzymatic kinetic resolution of rac -ibuprofen using immobilized lipase B of Candida antarctica as a biocatalyst. At the same time, one of the great problems of biocatalysis in organic media has been solved by eliminating excess water in the medium that allows the reversibility of the reaction. Following the optimization of the reaction conditions, an increase in enantiomeric excess and enantioselectivity was reached by using these acyl donors in the presence of a cosolvent.
format Article in Journal/Newspaper
author Oussama Khiari
Nassima Bouzemi
José María Sánchez-Montero
Andrés R. Alcántara
author_facet Oussama Khiari
Nassima Bouzemi
José María Sánchez-Montero
Andrés R. Alcántara
author_sort Oussama Khiari
title On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of ( S )-Ibuprofen
title_short On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of ( S )-Ibuprofen
title_full On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of ( S )-Ibuprofen
title_fullStr On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of ( S )-Ibuprofen
title_full_unstemmed On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of ( S )-Ibuprofen
title_sort on the use of orthoformates as an efficient approach to enhance the enzymatic enantioselective synthesis of ( s )-ibuprofen
publisher MDPI AG
publishDate 2023
url https://doi.org/10.3390/catal13020251
https://doaj.org/article/7963b5455ba144ab84b062a01601b1b0
genre Antarc*
Antarctica
genre_facet Antarc*
Antarctica
op_source Catalysts, Vol 13, Iss 2, p 251 (2023)
op_relation https://www.mdpi.com/2073-4344/13/2/251
https://doaj.org/toc/2073-4344
doi:10.3390/catal13020251
https://doaj.org/article/7963b5455ba144ab84b062a01601b1b0
op_doi https://doi.org/10.3390/catal13020251
container_title Catalysts
container_volume 13
container_issue 2
container_start_page 251
_version_ 1814718767254470656

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