Enantioselective transesterification of a propargyl tertiary alcohol by Candida antarctica lipase A: A reaction medium engineering approach
Lipase A from Candida antarctica (CAL-A) is widely known to accept bulky substrates, such as tertiary alcohols. These compounds are important building blocks in organic synthesis processes, and they are found in many natural products. Under an organic medium and in the presence of an acyl donor, CAL...
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| Format: | Article |
| Language: | English |
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Elsevier
2023-01-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715623002059 |
| _version_ | 1827920601448185856 |
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| author | Laerte Ganeo Neto Cintia Duarte Freitas Milagre Humberto Márcio Santos Milagre |
| author_facet | Laerte Ganeo Neto Cintia Duarte Freitas Milagre Humberto Márcio Santos Milagre |
| author_sort | Laerte Ganeo Neto |
| collection | DOAJ |
| description | Lipase A from Candida antarctica (CAL-A) is widely known to accept bulky substrates, such as tertiary alcohols. These compounds are important building blocks in organic synthesis processes, and they are found in many natural products. Under an organic medium and in the presence of an acyl donor, CAL-A can act as a chiral catalyst in the kinetic resolution (KR) of these substrates via an enantioselective transesterification reaction. Herein, we report a new protocol developed for the KR of the propargyl tertiary alcohol 2-phenyl-3-butyn-2-ol ((rac)-1) catalyzed by CAL-A. A reaction medium engineering study was performed by varying the following conditions involved in the system: temperature, solvent, acyl donor, acyl donor concentration, and enzyme loading. After optimization, we developed a more efficient system with a lower enzyme/substrate ratio using a commercially available and immobilized wild-type CAL-A. |
| first_indexed | 2024-03-13T04:12:58Z |
| format | Article |
| id | doaj.art-da4ea7588a764d51ac5d632fa615b97d |
| institution | Directory Open Access Journal |
| issn | 2211-7156 |
| language | English |
| last_indexed | 2024-03-13T04:12:58Z |
| publishDate | 2023-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj.art-da4ea7588a764d51ac5d632fa615b97d2023-06-21T06:52:45ZengElsevierResults in Chemistry2211-71562023-01-015100966Enantioselective transesterification of a propargyl tertiary alcohol by Candida antarctica lipase A: A reaction medium engineering approachLaerte Ganeo Neto0Cintia Duarte Freitas Milagre1Humberto Márcio Santos Milagre2Institute of Chemistry, São Paulo State University (UNESP), Prof. Francisco Degni, 55 – Quitandinha, Araraquara, São Paulo 14800-060, BrazilInstitute of Chemistry, São Paulo State University (UNESP), Prof. Francisco Degni, 55 – Quitandinha, Araraquara, São Paulo 14800-060, BrazilCorresponding author.; Institute of Chemistry, São Paulo State University (UNESP), Prof. Francisco Degni, 55 – Quitandinha, Araraquara, São Paulo 14800-060, BrazilLipase A from Candida antarctica (CAL-A) is widely known to accept bulky substrates, such as tertiary alcohols. These compounds are important building blocks in organic synthesis processes, and they are found in many natural products. Under an organic medium and in the presence of an acyl donor, CAL-A can act as a chiral catalyst in the kinetic resolution (KR) of these substrates via an enantioselective transesterification reaction. Herein, we report a new protocol developed for the KR of the propargyl tertiary alcohol 2-phenyl-3-butyn-2-ol ((rac)-1) catalyzed by CAL-A. A reaction medium engineering study was performed by varying the following conditions involved in the system: temperature, solvent, acyl donor, acyl donor concentration, and enzyme loading. After optimization, we developed a more efficient system with a lower enzyme/substrate ratio using a commercially available and immobilized wild-type CAL-A.http://www.sciencedirect.com/science/article/pii/S2211715623002059Propargyl tertiary alcoholLipaseKinetic resolutionEnantioselective transesterification |
| spellingShingle | Laerte Ganeo Neto Cintia Duarte Freitas Milagre Humberto Márcio Santos Milagre Enantioselective transesterification of a propargyl tertiary alcohol by Candida antarctica lipase A: A reaction medium engineering approach Results in Chemistry Propargyl tertiary alcohol Lipase Kinetic resolution Enantioselective transesterification |
| title | Enantioselective transesterification of a propargyl tertiary alcohol by Candida antarctica lipase A: A reaction medium engineering approach |
| title_full | Enantioselective transesterification of a propargyl tertiary alcohol by Candida antarctica lipase A: A reaction medium engineering approach |
| title_fullStr | Enantioselective transesterification of a propargyl tertiary alcohol by Candida antarctica lipase A: A reaction medium engineering approach |
| title_full_unstemmed | Enantioselective transesterification of a propargyl tertiary alcohol by Candida antarctica lipase A: A reaction medium engineering approach |
| title_short | Enantioselective transesterification of a propargyl tertiary alcohol by Candida antarctica lipase A: A reaction medium engineering approach |
| title_sort | enantioselective transesterification of a propargyl tertiary alcohol by candida antarctica lipase a a reaction medium engineering approach |
| topic | Propargyl tertiary alcohol Lipase Kinetic resolution Enantioselective transesterification |
| url | http://www.sciencedirect.com/science/article/pii/S2211715623002059 |
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