Biocatalytic Aldol Addition of Simple Aliphatic Nucleophiles to Hydroxyaldehydes

Raquel Roldán, Karel Hernandez, Jesús Joglar, Jordi Bujons, Teodor Parella, Israel Sánchez-Moreno, Virgil Hélaine, Marielle Lemaire, Christine Guérard-Hélaine, Wolf Dieter Fessner, Pere Clapés

    Research output: Contribution to journalArticleResearch

    14 Citations (Scopus)

    Abstract

    © 2018 American Chemical Society. 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).
    Original languageEnglish
    Pages (from-to)8804-8809
    JournalACS Catalysis
    Volume8
    DOIs
    Publication statusPublished - 7 Sep 2018

    Keywords

    • aldol reaction
    • aldolases
    • asymmetric catalysis
    • biocatalysis
    • carbon-carbon bond formation
    • deoxysugars
    • enzyme engineering

    Fingerprint Dive into the research topics of 'Biocatalytic Aldol Addition of Simple Aliphatic Nucleophiles to Hydroxyaldehydes'. Together they form a unique fingerprint.

    Cite this