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...
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ftmdpi:oai:mdpi.com:/2073-4344/9/6/522/ 2023-08-20T04:01:52+02:00 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 |
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Open Polar |
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MDPI Open Access Publishing |
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ftmdpi |
language |
English |
topic |
Enantioselectivity enzyme cascade hydroxynitrile lyase lipase hydrocyanation transesterification |
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 |
topic_facet |
Enantioselectivity enzyme cascade hydroxynitrile lyase lipase hydrocyanation transesterification |
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 |
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 |
title |
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_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_sort |
bienzymatic cascade for the synthesis of an optically active o-benzoyl cyanohydrin |
publisher |
Multidisciplinary Digital Publishing Institute |
publishDate |
2019 |
url |
https://doi.org/10.3390/catal9060522 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Catalysts; Volume 9; Issue 6; Pages: 522 |
op_relation |
Biocatalysis https://dx.doi.org/10.3390/catal9060522 |
op_rights |
https://creativecommons.org/licenses/by/4.0/ |
op_doi |
https://doi.org/10.3390/catal9060522 |
container_title |
Catalysts |
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9 |
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6 |
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522 |
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1774712246227697664 |