Journal
FEBS JOURNAL
Volume 282, Issue 7, Pages 1334-1345Publisher
WILEY-BLACKWELL
DOI: 10.1111/febs.13225
Keywords
biocatalytic carboxylation; enzyme deactivation; kinetic modelling; Kolbe-Schmitt reaction; nonoxidative carboxylation
Categories
Funding
- Austrian BMWFJ
- BMVIT
- SFG
- Standortagentur Tirol
- ZIT through the FFG-COMET
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Microbial decarboxylases, which catalyse the reversible regioselective ortho-carboxylation of phenolic derivatives in anaerobic detoxification pathways, have been studied for their reverse carboxylation activities on electron-rich aromatic substrates. Ortho-hydroxybenzoic acids are important building blocks in the chemical and pharmaceutical industries and are currently produced via the Kolbe-Schmitt process, which requires elevated pressures and temperatures (5bar, 100 degrees C) and often shows incomplete regioselectivities. In order to resolve bottlenecks in view of preparative-scale applications, we studied the kinetic parameters for 2,6-dihydroxybenzoic acid decarboxylase from Rhizobiumsp. in the carboxylation- and decarboxylation-direction using 1,2-dihydroxybenzene (catechol) as starting material. The catalytic properties (K-m, V-max) are correlated with the overall thermodynamic equilibrium via the Haldane equation, according to a reversible random bi-uni mechanism. The model was subsequently verified by comparing experimental results with simulations. This study provides insights into the catalytic behaviour of a nonoxidative aromatic decarboxylase and reveals key limitations (e.g. substrate oxidation, CO2 pressure, enzyme deactivation, low turnover frequency) in view of the employment of this system as a green' alternative to the Kolbe-Schmitt processes.
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