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

Autor:	Godwin A. Aleku, Silvia M. Glueck, Karl A. P. Payne, Ruth T. Bradshaw-Allen, David A. Parker, Katharina Plasch, Samuel S. Bailey, Kurt Faber, Christoph Prause, David Leys
Rok vydání:	2018
Předmět:	Stereochemistry Decarboxylation Prenyltransferase Flavin group 010402 general chemistry 01 natural sciences Catalysis Cofactor Cinnamic acid Inorganic Chemistry Ferulic acid chemistry.chemical_compound Manchester Institute of Biotechnology Terminal alkenes Physical and Theoretical Chemistry biology Full Paper Ferulic acid decarboxylase 010405 organic chemistry Chemistry Organic Chemistry Full Papers ResearchInstitutes_Networks_Beacons/manchester_institute_of_biotechnology 0104 chemical sciences Carboxylation Biocatalysis biology.protein Prenylated flavin
Zdroj:	ChemCatChem Chemcatchem Aleku, G A, Prause, C, Bradshaw-Allen, R T, Plasch, K, Glueck, S M, Bailey, S S, Payne, K A P, Parker, D A, Faber, K & Leys, D 2018, ' Terminal Alkenes from Acrylic Acid Derivatives via Non-Oxidative Enzymatic Decarboxylation by Ferulic Acid Decarboxylases ', ChemCatChem, vol. 10, no. 17, pp. 3736-3745 . https://doi.org/10.1002/cctc.201800643
ISSN:	1867-3880
DOI:	10.1002/cctc.201800643
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::d47da3d88bac37e5b51a070c1718f0cb https://pubmed.ncbi.nlm.nih.gov/30333895 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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