Two Approaches for CAL-B-Catalyzed Enantioselective Deacylation of a Set of α-Phenyl Ethyl Esters: Organic Solvent with Sodium Carbonate and Micro-aqueous Medium
International audience Herein, we report an efficient enantioselective cleavage of the acyl-moiety of a set of α-phenyl ethyl esters with different chain-lengths catalyzed by lipase B from Candida antarctica (CAL-B) by comparing two reactional approaches: anhydrous media with sodium carbonates and m...
Published in: | Catalysis Letters |
---|---|
Main Authors: | , , , , , |
Other Authors: | , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
HAL CCSD
2021
|
Subjects: | |
Online Access: | https://hal.science/hal-03304163 https://hal.science/hal-03304163v1/document https://hal.science/hal-03304163v1/file/Cat%20Letr%202021%20HAL.pdf https://doi.org/10.1007/s10562-020-03525-0 |
id |
ftuniparissaclay:oai:HAL:hal-03304163v1 |
---|---|
record_format |
openpolar |
spelling |
ftuniparissaclay:oai:HAL:hal-03304163v1 2024-10-20T14:04:13+00:00 Two Approaches for CAL-B-Catalyzed Enantioselective Deacylation of a Set of α-Phenyl Ethyl Esters: Organic Solvent with Sodium Carbonate and Micro-aqueous Medium Razi, Samra Zeror, Saoussen Merabet-Khelassi, Mounia Kolodziej, Emilie Toffano, Martial Aribi-Zouioueche, Louisa Université Badji Mokhtar Annaba (UBMA) Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO) Institut de Chimie - CNRS Chimie (INC-CNRS)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS) 2021 https://hal.science/hal-03304163 https://hal.science/hal-03304163v1/document https://hal.science/hal-03304163v1/file/Cat%20Letr%202021%20HAL.pdf https://doi.org/10.1007/s10562-020-03525-0 en eng HAL CCSD Springer Verlag info:eu-repo/semantics/altIdentifier/doi/10.1007/s10562-020-03525-0 hal-03304163 https://hal.science/hal-03304163 https://hal.science/hal-03304163v1/document https://hal.science/hal-03304163v1/file/Cat%20Letr%202021%20HAL.pdf doi:10.1007/s10562-020-03525-0 info:eu-repo/semantics/OpenAccess ISSN: 1011-372X EISSN: 1572-879X Catalysis Letters https://hal.science/hal-03304163 Catalysis Letters, In press, ⟨10.1007/s10562-020-03525-0⟩ Kinetic resolution CAL-B deacylation Na2CO3 α-phenyl ethyl esters flavoring agent Anhydrous medium Micro-aqueous medium [CHIM.ORGA]Chemical Sciences/Organic chemistry [CHIM.CATA]Chemical Sciences/Catalysis info:eu-repo/semantics/article Journal articles 2021 ftuniparissaclay https://doi.org/10.1007/s10562-020-03525-0 2024-09-20T00:21:17Z International audience Herein, we report an efficient enantioselective cleavage of the acyl-moiety of a set of α-phenyl ethyl esters with different chain-lengths catalyzed by lipase B from Candida antarctica (CAL-B) by comparing two reactional approaches: anhydrous media with sodium carbonates and micro-aqueous medium. The deacylation is performed in organic solvent, in the presence of Na2CO3 in the first case, and by addition of a drop of phosphate buffer solution pH=7 in the second. The results show the high efficiency of the deacylation in the presence of the sodium carbonate for the enzymatic resolution of all the esters and that in term of reactivity (31% ≤ conv ≤ 50%) and selectivity (E >200). While, during the hydrolysis in micro-aqueous media, the conversion is strongly affected by the length of the acyl-chain side, the conversion decreases from conv =50% with the 1-phenylethyl acetate 1a to conv =19% with 1-phenyethyl dodecanoate 6a, and this, even if the selectivity remains high (E>89). In both conditions, the lipase CAL-B shows a high enantioselectivities in favor of (R)-1-phenyl ethanol enantiomer (conv >45%, E>200) but the reactivity is modulated by the form and the size of the acyl-chain side. Article in Journal/Newspaper Antarc* Antarctica Archives ouvertes de Paris-Saclay Catalysis Letters 151 9 2603 2611 |
institution |
Open Polar |
collection |
Archives ouvertes de Paris-Saclay |
op_collection_id |
ftuniparissaclay |
language |
English |
topic |
Kinetic resolution CAL-B deacylation Na2CO3 α-phenyl ethyl esters flavoring agent Anhydrous medium Micro-aqueous medium [CHIM.ORGA]Chemical Sciences/Organic chemistry [CHIM.CATA]Chemical Sciences/Catalysis |
spellingShingle |
Kinetic resolution CAL-B deacylation Na2CO3 α-phenyl ethyl esters flavoring agent Anhydrous medium Micro-aqueous medium [CHIM.ORGA]Chemical Sciences/Organic chemistry [CHIM.CATA]Chemical Sciences/Catalysis Razi, Samra Zeror, Saoussen Merabet-Khelassi, Mounia Kolodziej, Emilie Toffano, Martial Aribi-Zouioueche, Louisa Two Approaches for CAL-B-Catalyzed Enantioselective Deacylation of a Set of α-Phenyl Ethyl Esters: Organic Solvent with Sodium Carbonate and Micro-aqueous Medium |
topic_facet |
Kinetic resolution CAL-B deacylation Na2CO3 α-phenyl ethyl esters flavoring agent Anhydrous medium Micro-aqueous medium [CHIM.ORGA]Chemical Sciences/Organic chemistry [CHIM.CATA]Chemical Sciences/Catalysis |
description |
International audience Herein, we report an efficient enantioselective cleavage of the acyl-moiety of a set of α-phenyl ethyl esters with different chain-lengths catalyzed by lipase B from Candida antarctica (CAL-B) by comparing two reactional approaches: anhydrous media with sodium carbonates and micro-aqueous medium. The deacylation is performed in organic solvent, in the presence of Na2CO3 in the first case, and by addition of a drop of phosphate buffer solution pH=7 in the second. The results show the high efficiency of the deacylation in the presence of the sodium carbonate for the enzymatic resolution of all the esters and that in term of reactivity (31% ≤ conv ≤ 50%) and selectivity (E >200). While, during the hydrolysis in micro-aqueous media, the conversion is strongly affected by the length of the acyl-chain side, the conversion decreases from conv =50% with the 1-phenylethyl acetate 1a to conv =19% with 1-phenyethyl dodecanoate 6a, and this, even if the selectivity remains high (E>89). In both conditions, the lipase CAL-B shows a high enantioselectivities in favor of (R)-1-phenyl ethanol enantiomer (conv >45%, E>200) but the reactivity is modulated by the form and the size of the acyl-chain side. |
author2 |
Université Badji Mokhtar Annaba (UBMA) Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO) Institut de Chimie - CNRS Chimie (INC-CNRS)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS) |
format |
Article in Journal/Newspaper |
author |
Razi, Samra Zeror, Saoussen Merabet-Khelassi, Mounia Kolodziej, Emilie Toffano, Martial Aribi-Zouioueche, Louisa |
author_facet |
Razi, Samra Zeror, Saoussen Merabet-Khelassi, Mounia Kolodziej, Emilie Toffano, Martial Aribi-Zouioueche, Louisa |
author_sort |
Razi, Samra |
title |
Two Approaches for CAL-B-Catalyzed Enantioselective Deacylation of a Set of α-Phenyl Ethyl Esters: Organic Solvent with Sodium Carbonate and Micro-aqueous Medium |
title_short |
Two Approaches for CAL-B-Catalyzed Enantioselective Deacylation of a Set of α-Phenyl Ethyl Esters: Organic Solvent with Sodium Carbonate and Micro-aqueous Medium |
title_full |
Two Approaches for CAL-B-Catalyzed Enantioselective Deacylation of a Set of α-Phenyl Ethyl Esters: Organic Solvent with Sodium Carbonate and Micro-aqueous Medium |
title_fullStr |
Two Approaches for CAL-B-Catalyzed Enantioselective Deacylation of a Set of α-Phenyl Ethyl Esters: Organic Solvent with Sodium Carbonate and Micro-aqueous Medium |
title_full_unstemmed |
Two Approaches for CAL-B-Catalyzed Enantioselective Deacylation of a Set of α-Phenyl Ethyl Esters: Organic Solvent with Sodium Carbonate and Micro-aqueous Medium |
title_sort |
two approaches for cal-b-catalyzed enantioselective deacylation of a set of α-phenyl ethyl esters: organic solvent with sodium carbonate and micro-aqueous medium |
publisher |
HAL CCSD |
publishDate |
2021 |
url |
https://hal.science/hal-03304163 https://hal.science/hal-03304163v1/document https://hal.science/hal-03304163v1/file/Cat%20Letr%202021%20HAL.pdf https://doi.org/10.1007/s10562-020-03525-0 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
ISSN: 1011-372X EISSN: 1572-879X Catalysis Letters https://hal.science/hal-03304163 Catalysis Letters, In press, ⟨10.1007/s10562-020-03525-0⟩ |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.1007/s10562-020-03525-0 hal-03304163 https://hal.science/hal-03304163 https://hal.science/hal-03304163v1/document https://hal.science/hal-03304163v1/file/Cat%20Letr%202021%20HAL.pdf doi:10.1007/s10562-020-03525-0 |
op_rights |
info:eu-repo/semantics/OpenAccess |
op_doi |
https://doi.org/10.1007/s10562-020-03525-0 |
container_title |
Catalysis Letters |
container_volume |
151 |
container_issue |
9 |
container_start_page |
2603 |
op_container_end_page |
2611 |
_version_ |
1813452877174145024 |