Bienzymatic Cascade for the Synthesis of an Optically Active O-benzoyl Cyanohydrin
A concurrent bienzymatic cascade for the synthesis of optically pure (S)-4-methoxymandelonitrile benzoate ((S)-3) starting from 4-anisaldehyde (1) has been developed. The cascade involves an enantioselective Manihot esculenta hydroxynitrile lyase-catalyzed hydrocyanation of 1, and the subsequent ben...
| Published in: | Catalysts |
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| Main Authors: | , , , |
| Format: | Text |
| Language: | English |
| Published: |
Multidisciplinary Digital Publishing Institute
2019
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| Subjects: | |
| Online Access: | https://doi.org/10.3390/catal9060522 |
| _version_ | 1821759925761605632 |
|---|---|
| author | Laura Leemans Luuk van Langen Frank Hollmann Anett Schallmey |
| author_facet | Laura Leemans Luuk van Langen Frank Hollmann Anett Schallmey |
| author_sort | Laura Leemans |
| collection | MDPI Open Access Publishing |
| container_issue | 6 |
| container_start_page | 522 |
| container_title | Catalysts |
| container_volume | 9 |
| description | A concurrent bienzymatic cascade for the synthesis of optically pure (S)-4-methoxymandelonitrile benzoate ((S)-3) starting from 4-anisaldehyde (1) has been developed. The cascade involves an enantioselective Manihot esculenta hydroxynitrile lyase-catalyzed hydrocyanation of 1, and the subsequent benzoylation of the resulting cyanohydrin (S)-2 catalyzed by Candida antarctica lipase A in organic solvent. To accomplish this new direct synthesis of the protected enantiopure cyanohydrin, both enzymes were immobilized and each biocatalytic step was studied separately in search for a window of compatibility. In addition, potential cross-interactions between the two reactions were identified. Optimization of the cascade resulted in 81% conversion of the aldehyde to the corresponding benzoyl cyanohydrin with 98% enantiomeric excess. |
| format | Text |
| genre | Antarc* Antarctica |
| genre_facet | Antarc* Antarctica |
| id | ftmdpi:oai:mdpi.com:/2073-4344/9/6/522/ |
| institution | Open Polar |
| language | English |
| op_collection_id | ftmdpi |
| op_doi | https://doi.org/10.3390/catal9060522 |
| op_relation | Biocatalysis https://dx.doi.org/10.3390/catal9060522 |
| op_rights | https://creativecommons.org/licenses/by/4.0/ |
| op_source | Catalysts; Volume 9; Issue 6; Pages: 522 |
| publishDate | 2019 |
| publisher | Multidisciplinary Digital Publishing Institute |
| record_format | openpolar |
| spelling | ftmdpi:oai:mdpi.com:/2073-4344/9/6/522/ 2025-01-16T19:27:42+00:00 Bienzymatic Cascade for the Synthesis of an Optically Active O-benzoyl Cyanohydrin Laura Leemans Luuk van Langen Frank Hollmann Anett Schallmey 2019-06-12 application/pdf https://doi.org/10.3390/catal9060522 EN eng Multidisciplinary Digital Publishing Institute Biocatalysis https://dx.doi.org/10.3390/catal9060522 https://creativecommons.org/licenses/by/4.0/ Catalysts; Volume 9; Issue 6; Pages: 522 Enantioselectivity enzyme cascade hydroxynitrile lyase lipase hydrocyanation transesterification Text 2019 ftmdpi https://doi.org/10.3390/catal9060522 2023-07-31T22:21:07Z A concurrent bienzymatic cascade for the synthesis of optically pure (S)-4-methoxymandelonitrile benzoate ((S)-3) starting from 4-anisaldehyde (1) has been developed. The cascade involves an enantioselective Manihot esculenta hydroxynitrile lyase-catalyzed hydrocyanation of 1, and the subsequent benzoylation of the resulting cyanohydrin (S)-2 catalyzed by Candida antarctica lipase A in organic solvent. To accomplish this new direct synthesis of the protected enantiopure cyanohydrin, both enzymes were immobilized and each biocatalytic step was studied separately in search for a window of compatibility. In addition, potential cross-interactions between the two reactions were identified. Optimization of the cascade resulted in 81% conversion of the aldehyde to the corresponding benzoyl cyanohydrin with 98% enantiomeric excess. Text Antarc* Antarctica MDPI Open Access Publishing Catalysts 9 6 522 |
| spellingShingle | Enantioselectivity enzyme cascade hydroxynitrile lyase lipase hydrocyanation transesterification Laura Leemans Luuk van Langen Frank Hollmann Anett Schallmey Bienzymatic Cascade for the Synthesis of an Optically Active O-benzoyl Cyanohydrin |
| title | Bienzymatic Cascade for the Synthesis of an Optically Active O-benzoyl Cyanohydrin |
| title_full | Bienzymatic Cascade for the Synthesis of an Optically Active O-benzoyl Cyanohydrin |
| title_fullStr | Bienzymatic Cascade for the Synthesis of an Optically Active O-benzoyl Cyanohydrin |
| title_full_unstemmed | Bienzymatic Cascade for the Synthesis of an Optically Active O-benzoyl Cyanohydrin |
| title_short | Bienzymatic Cascade for the Synthesis of an Optically Active O-benzoyl Cyanohydrin |
| title_sort | bienzymatic cascade for the synthesis of an optically active o-benzoyl cyanohydrin |
| topic | Enantioselectivity enzyme cascade hydroxynitrile lyase lipase hydrocyanation transesterification |
| topic_facet | Enantioselectivity enzyme cascade hydroxynitrile lyase lipase hydrocyanation transesterification |
| url | https://doi.org/10.3390/catal9060522 |