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 |
|---|---|
| Main Authors: | , , , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
MDPI AG
2019
|
| Subjects: | |
| Online Access: | https://doi.org/10.3390/catal9060522 https://nbn-resolving.org/urn:nbn:de:gbv:084-2019061413343 https://leopard.tu-braunschweig.de/receive/dbbs_mods_00066693 https://leopard.tu-braunschweig.de/servlets/MCRFileNodeServlet/dbbs_derivate_00045436/Schallmey-catalysts-09-00522.pdf http://publikationsserver.tu-braunschweig.de/get/66693 |
| Summary: | 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. |
|---|