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Biocatalytic Aldol Addition of Simple Aliphatic Nucleophiles to Hydroxyaldehydes

AuthorsRoldán, Raquel; Hernández Sánchez, Karel ; Joglar Tamargo, Jesús ; Bujons, Jordi; Parella, Teodor; Sánchez-Moreno, Israel ; Hélaine, Virgil; Lemaire, Marielle; Guérard-Hélaine, Christine; Fessner, Wolf Dieter; Clapés Saborit, Pere
KeywordsAldol reaction
Asymmetric catalysis
Carbon-Carbon bond formation
Enzyme Engineering
Issue Date8-Aug-2018
PublisherAmerican Chemical Society
CitationACS Catalysis 8804–8809 (2018)
AbstractAsymmetric 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.
Publisher version (URL)https://pubs.acs.org/doi/10.1021/acscatal.8b02486
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