Terminal Alkenes from Acrylic Acid Derivatives via Non-Oxidative Enzymatic Decarboxylation by Ferulic Acid Decarboxylases

Godwin A. Aleku, Christoph Prause, Ruth T. Bradshaw-Allen, Katharina Plasch, Silvia M. Glueck, Samuel S. Bailey, Karl A.P. Payne, David A. Parker, Kurt Faber, David Leys

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Fungal ferulic acid decarboxylases (FDCs) belong to the UbiD-family of enzymes and catalyse the reversible (de)carboxylation of cinnamic acid derivatives through the use of a prenylated flavin cofactor. The latter is synthesised by the flavin prenyltransferase UbiX. Herein, we demonstrate the applicability of FDC/UbiX expressing cells for both isolated enzyme and whole-cell biocatalysis. FDCs exhibit high activity with total turnover numbers (TTN) of up to 55000 and turnover frequency (TOF) of up to 370 min−1. Co-solvent compatibility studies revealed FDC's tolerance to some organic solvents up 20 % v/v. Using the in-vitro (de)carboxylase activity of holo-FDC as well as whole-cell biocatalysts, we performed a substrate profiling study of three FDCs, providing insights into structural determinants of activity. FDCs display broad substrate tolerance towards a wide range of acrylic acid derivatives bearing (hetero)cyclic or olefinic substituents at C3 affording conversions of up to >99 %. The synthetic utility of FDCs was demonstrated by a preparative-scale decarboxylation.

    Original languageEnglish
    Pages (from-to)3736-3745
    Number of pages10
    JournalChemCatChem
    Volume10
    Issue number17
    Early online date20 Jun 2018
    DOIs
    Publication statusPublished - 17 Jul 2018

    Keywords

    • Biocatalysis
    • Decarboxylation
    • Ferulic acid decarboxylase
    • Prenylated flavin
    • Terminal alkenes

    Research Beacons, Institutes and Platforms

    • Manchester Institute of Biotechnology

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