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Article Dans Une Revue ACS Catalysis Année : 2018

Biocatalytic Aldol Addition of Simple Aliphatic Nucleophiles to Hydroxyaldehydes

Résumé

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 ethanal and nonfunctionalized linear and cyclic aliphatic ketones as nucleophiles to nonphosphorylated 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).

Dates et versions

hal-02067319 , version 1 (14-03-2019)

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Citer

Raquel Roldán, Karel Hernández, Jesús Joglar, Jordi Bujons, Teodor Parella, et al.. Biocatalytic Aldol Addition of Simple Aliphatic Nucleophiles to Hydroxyaldehydes. ACS Catalysis, 2018, 8 (9), pp.8804-8809. ⟨10.1021/acscatal.8b02486⟩. ⟨hal-02067319⟩
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