Breaking the Dogma of Aldolase Specificity: Simple Aliphatic Ketones and Aldehydes are Nucleophiles for Fructose-6-phosphate Aldolase

Raquel Roldán, Israel Sanchez-Moreno, Thomas Scheidt, Virgil Hélaine, Marielle Lemaire, Teodor Parella, Pere Clapés, Wolf Dieter Fessner, Christine Guérard-Hélaine

    Research output: Contribution to journalArticleResearchpeer-review

    23 Citations (Scopus)

    Abstract

    © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim d-Fructose-6-phosphate aldolase (FSA) was probed for extended nucleophile promiscuity by using a series of fluorogenic substrates to reveal retro-aldol activity. Four nucleophiles ethanal, propanone, butanone, and cyclopentanone were subsequently confirmed to be non-natural substrates in the synthesis direction using the wild-type enzyme and its D6H variant. This exceptional widening of the nucleophile substrate scope offers a rapid entry, in good yields and high stereoselectivity, to less oxygenated alkyl ketones and aldehydes, which was hitherto impossible.
    Original languageEnglish
    Pages (from-to)5005-5009
    JournalChemistry - A European Journal
    Volume23
    Issue number21
    DOIs
    Publication statusPublished - 11 Apr 2017

    Keywords

    • aldolization
    • biocatalysis
    • enzymes
    • fructose-6-phosphate aldolase
    • phosphorylated compounds

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