Understanding water effect on Candida antarctica lipase B activity and enantioselectivity towards secondary alcohols.
6 pages International audience The effect of water activity (aW) on Candida antarctica lipase B (CALB) activity and enantioselectivity towards secondary alcohols was assessed. Experimental results for the resolution of racemic pentan-2-ol, hexan-3-ol, butan-2-ol and octan-4-ol by immobilized CALB-ca...
Published in: | Journal of Molecular Catalysis B: Enzymatic |
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Format: | Article in Journal/Newspaper |
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Online Access: | https://hal.archives-ouvertes.fr/hal-00647583 https://hal.archives-ouvertes.fr/hal-00647583/document https://hal.archives-ouvertes.fr/hal-00647583/file/corrected-effet_aw_2_submitted_JMolCatB.pdf https://doi.org/10.1016/j.molcatb.2009.01.008 |
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ftccsdartic:oai:HAL:hal-00647583v1 2023-05-15T14:00:47+02:00 Understanding water effect on Candida antarctica lipase B activity and enantioselectivity towards secondary alcohols. Léonard, Valérie Marton, Z. Lamare, Sylvain Hult, Karl Graber, Marianne LIttoral ENvironnement et Sociétés - UMRi 7266 (LIENSs) Université de La Rochelle (ULR)-Centre National de la Recherche Scientifique (CNRS) Department of Biochemistry- KTH Royal Institute of Technology Stockholm (KTH ) 2009-04-02 https://hal.archives-ouvertes.fr/hal-00647583 https://hal.archives-ouvertes.fr/hal-00647583/document https://hal.archives-ouvertes.fr/hal-00647583/file/corrected-effet_aw_2_submitted_JMolCatB.pdf https://doi.org/10.1016/j.molcatb.2009.01.008 en eng HAL CCSD Elsevier info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcatb.2009.01.008 hal-00647583 https://hal.archives-ouvertes.fr/hal-00647583 https://hal.archives-ouvertes.fr/hal-00647583/document https://hal.archives-ouvertes.fr/hal-00647583/file/corrected-effet_aw_2_submitted_JMolCatB.pdf doi:10.1016/j.molcatb.2009.01.008 info:eu-repo/semantics/OpenAccess ISSN: 1381-1177 Journal of Molecular Catalysis B: Enzymatic https://hal.archives-ouvertes.fr/hal-00647583 Journal of Molecular Catalysis B: Enzymatic, Elsevier, 2009, 59, pp.90-95. ⟨10.1016/j.molcatb.2009.01.008⟩ Lipase Stereoselective catalysis Thermodynamics Thermodynamic activity of water Water adsorption [SDV.BIO]Life Sciences [q-bio]/Biotechnology [INFO.INFO-BT]Computer Science [cs]/Biotechnology info:eu-repo/semantics/article Journal articles 2009 ftccsdartic https://doi.org/10.1016/j.molcatb.2009.01.008 2021-10-24T17:06:52Z 6 pages International audience The effect of water activity (aW) on Candida antarctica lipase B (CALB) activity and enantioselectivity towards secondary alcohols was assessed. Experimental results for the resolution of racemic pentan-2-ol, hexan-3-ol, butan-2-ol and octan-4-ol by immobilized CALB-catalyzed acylation with methyl propanoate, were obtained by using a solid/gas reactor. Water and substrate adsorption mechanism on immobilized CALB, were then studied using moisture sorption analyzer and inverse gas chromatography, and the effective hydration state of the biocatalyst when varying aW was defined. The data showed a pronounced aW effect on both activity and enantioselectivity. If secondary alcohol follows the steric rules for being efficiently resolved, water at very low aW increased enantioselectivity by acting predominantly as an enantioselective inhibitor, making the stereospecificity pocket smaller. When increasing aW, water decreased enantioselectivity, due to an unfavourable increase of the entropic term TR-SS‡ of the differential free energy of activation. The "turning point" at which water changed from one predominant role to another would correspond to aW allowing full coverage of polar groups of the immobilized biocatalyst by water molecules. Article in Journal/Newspaper Antarc* Antarctica Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) Journal of Molecular Catalysis B: Enzymatic 59 1-3 90 95 |
institution |
Open Polar |
collection |
Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) |
op_collection_id |
ftccsdartic |
language |
English |
topic |
Lipase Stereoselective catalysis Thermodynamics Thermodynamic activity of water Water adsorption [SDV.BIO]Life Sciences [q-bio]/Biotechnology [INFO.INFO-BT]Computer Science [cs]/Biotechnology |
spellingShingle |
Lipase Stereoselective catalysis Thermodynamics Thermodynamic activity of water Water adsorption [SDV.BIO]Life Sciences [q-bio]/Biotechnology [INFO.INFO-BT]Computer Science [cs]/Biotechnology Léonard, Valérie Marton, Z. Lamare, Sylvain Hult, Karl Graber, Marianne Understanding water effect on Candida antarctica lipase B activity and enantioselectivity towards secondary alcohols. |
topic_facet |
Lipase Stereoselective catalysis Thermodynamics Thermodynamic activity of water Water adsorption [SDV.BIO]Life Sciences [q-bio]/Biotechnology [INFO.INFO-BT]Computer Science [cs]/Biotechnology |
description |
6 pages International audience The effect of water activity (aW) on Candida antarctica lipase B (CALB) activity and enantioselectivity towards secondary alcohols was assessed. Experimental results for the resolution of racemic pentan-2-ol, hexan-3-ol, butan-2-ol and octan-4-ol by immobilized CALB-catalyzed acylation with methyl propanoate, were obtained by using a solid/gas reactor. Water and substrate adsorption mechanism on immobilized CALB, were then studied using moisture sorption analyzer and inverse gas chromatography, and the effective hydration state of the biocatalyst when varying aW was defined. The data showed a pronounced aW effect on both activity and enantioselectivity. If secondary alcohol follows the steric rules for being efficiently resolved, water at very low aW increased enantioselectivity by acting predominantly as an enantioselective inhibitor, making the stereospecificity pocket smaller. When increasing aW, water decreased enantioselectivity, due to an unfavourable increase of the entropic term TR-SS‡ of the differential free energy of activation. The "turning point" at which water changed from one predominant role to another would correspond to aW allowing full coverage of polar groups of the immobilized biocatalyst by water molecules. |
author2 |
LIttoral ENvironnement et Sociétés - UMRi 7266 (LIENSs) Université de La Rochelle (ULR)-Centre National de la Recherche Scientifique (CNRS) Department of Biochemistry- KTH Royal Institute of Technology Stockholm (KTH ) |
format |
Article in Journal/Newspaper |
author |
Léonard, Valérie Marton, Z. Lamare, Sylvain Hult, Karl Graber, Marianne |
author_facet |
Léonard, Valérie Marton, Z. Lamare, Sylvain Hult, Karl Graber, Marianne |
author_sort |
Léonard, Valérie |
title |
Understanding water effect on Candida antarctica lipase B activity and enantioselectivity towards secondary alcohols. |
title_short |
Understanding water effect on Candida antarctica lipase B activity and enantioselectivity towards secondary alcohols. |
title_full |
Understanding water effect on Candida antarctica lipase B activity and enantioselectivity towards secondary alcohols. |
title_fullStr |
Understanding water effect on Candida antarctica lipase B activity and enantioselectivity towards secondary alcohols. |
title_full_unstemmed |
Understanding water effect on Candida antarctica lipase B activity and enantioselectivity towards secondary alcohols. |
title_sort |
understanding water effect on candida antarctica lipase b activity and enantioselectivity towards secondary alcohols. |
publisher |
HAL CCSD |
publishDate |
2009 |
url |
https://hal.archives-ouvertes.fr/hal-00647583 https://hal.archives-ouvertes.fr/hal-00647583/document https://hal.archives-ouvertes.fr/hal-00647583/file/corrected-effet_aw_2_submitted_JMolCatB.pdf https://doi.org/10.1016/j.molcatb.2009.01.008 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
ISSN: 1381-1177 Journal of Molecular Catalysis B: Enzymatic https://hal.archives-ouvertes.fr/hal-00647583 Journal of Molecular Catalysis B: Enzymatic, Elsevier, 2009, 59, pp.90-95. ⟨10.1016/j.molcatb.2009.01.008⟩ |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcatb.2009.01.008 hal-00647583 https://hal.archives-ouvertes.fr/hal-00647583 https://hal.archives-ouvertes.fr/hal-00647583/document https://hal.archives-ouvertes.fr/hal-00647583/file/corrected-effet_aw_2_submitted_JMolCatB.pdf doi:10.1016/j.molcatb.2009.01.008 |
op_rights |
info:eu-repo/semantics/OpenAccess |
op_doi |
https://doi.org/10.1016/j.molcatb.2009.01.008 |
container_title |
Journal of Molecular Catalysis B: Enzymatic |
container_volume |
59 |
container_issue |
1-3 |
container_start_page |
90 |
op_container_end_page |
95 |
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1766270123171119104 |