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


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.

SUBMITTER: Aleku GA 

PROVIDER: S-EPMC6175315 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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

Aleku Godwin A GA   Prause Christoph C   Bradshaw-Allen Ruth T RT   Plasch Katharina K   Glueck Silvia M SM   Bailey Samuel S SS   Payne Karl A P KAP   Parker David A DA   Faber Kurt K   Leys David D  

ChemCatChem 20180717 17


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 u  ...[more]

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