Bioreduction of β-ketosulfides Using Deep Eutectic Solvents as Cosolvents
The β-hydroxysulfide motif is present in both natural and synthetic compounds with notable bioactivities. Herein, the synthesis of aset of optically active (R)- and (S)-β-hydroxysulfides starting from β-ketosulfides using ketoreductases (KREDs) in nonconventionalmedia aqueous buffer/deep eutectic so...
| Autores: | , , , , , , |
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| Formato: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2026 |
| País: | España |
| Recursos: | Universidad de Sevilla (US) |
| Repositorio: | idUS. Depósito de Investigación de la Universidad de Sevilla |
| OAI Identifier: | oai:dnet:idus________::4ab4a43b2d6bb506b3807f3a1967b604 |
| Acesso em linha: | https://hdl.handle.net/11441/186153 https://doi.org/10.1002/cctc.202501617 |
| Access Level: | acceso abierto |
| Palavra-chave: | Alcohol dehydrogenases Deep eutectic solvents Lipases Sequential reaction β-hydroxysulfides |
| Resumo: | The β-hydroxysulfide motif is present in both natural and synthetic compounds with notable bioactivities. Herein, the synthesis of aset of optically active (R)- and (S)-β-hydroxysulfides starting from β-ketosulfides using ketoreductases (KREDs) in nonconventionalmedia aqueous buffer/deep eutectic solvents (DESs) has been developed. Several Type III DESs have been tested as cosolvents,being observed for most of the biotransformations higher conversions and enantiomeric excesses in the presence of some glycerol-or ethylenglycol-based DESs. Bioreductions can be performed up to 70% v/v of DESs with good conversions, demonstratingthe high performance of these nonconventional media in biocatalyzed reductive processes. Additionally, it was observed thatthe lipase CalB partially retained activity in DES-containing media for the hydrolysis of β-alkylsulfide enol esters, thus beingpossible to develop a one-pot, two-enzyme cascade that combined CaalB-catalyzed hydrolysis of a β-alkylsulfide enol ester withthe subsequent KRED reduction of the β-ketosulfide obtained to the (R)-β-hydroxysulfide in both sequential and concurrent ways,affording high stereoselectivity. |
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