Biocatalytic Aldol Addition of Simple Aliphatic Nucleophiles to Hydroxyaldehydes
Asymmetric aldol addition of simple aldehydes and ketones to electrophiles is a cornerstone reaction for the synthesis of unusual sugars and chiral building blocks. We investigated D-fructose-6-phosphate aldolase from E. coli (FSA) D6X variants as catalysts for the aldol additions of linear and cycl...
| Autores: | , , , , , , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2018 |
| País: | España |
| Institución: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositorio: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/169343 |
| Acceso en línea: | http://hdl.handle.net/10261/169343 |
| Access Level: | acceso abierto |
| Palabra clave: | Aldol reaction Aldolases Asymmetric catalysis Biocatalysis Carbon-Carbon bond formation Deoxysugars Enzyme Engineering |
| Sumario: | Asymmetric aldol addition of simple aldehydes and ketones to electrophiles is a cornerstone reaction for the synthesis of unusual sugars and chiral building blocks. We investigated D-fructose-6-phosphate aldolase from E. coli (FSA) D6X variants as catalysts for the aldol additions of linear and cyclic non-functionalized aliphatic ketones or ethanal as nucleophiles to non-phosphorylated hydroxyaldehydes. Thus, addition of propanone, cyclobutanone, cyclopentanone or ethanal to 3-hydroxypropanal or (S)- or (R)-3-hydroxybutanal catalyzed by FSA D6H and D6Q variants furnished rare deoxysugars in 8-77% isolated yields with high stereoselectivity (97:3 dr and >95% ee). © 2018 American Chemical Society. |
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