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Pushing the equilibrium of regio-complementary carboxylation of phenols and hydroxystyrene derivatives

Paper ID Volume ID Publish Year Pages File Format Full-Text
23481 43441 2013 7 PDF Available
Title
Pushing the equilibrium of regio-complementary carboxylation of phenols and hydroxystyrene derivatives
Abstract

•Significantly enhanced conversions of ortho-carboxylation in presence of water-miscible organic co-solvents.•Broad operating window in terms of reaction temperature, substrate concentration and bicarbonate source.•Reusability of the biocatalyst over several cycles without loss of activity.

The enzymatic carboxylation of electron-rich aromatics, which represents a promising ‘green’ equivalent to the chemical Kolbe–Schmitt reaction, is thermodynamically disfavored and is therefore impeded by incomplete conversions. Optimization of the reaction conditions, such as pH, temperature, substrate concentration and the use of organic co-solvents and/or ionic liquids allowed to push the conversion in favor of carboxylation by a factor of up to 50%. Careful selection of the type of bicarbonate salt used as CO2 source was crucial to ensure optimal activities. Among two types of carboxylases tested with their natural substrates, benzoic acid decarboxylase from Rhizobium sp. proved to be significantly more stable than phenolic acid decarboxylase from Mycobacterium colombiense; it tolerated reaction temperatures of up to 50 °C and substrate concentrations of up to 100 mM and allowed efficient biocatalyst recycling.

Keywords
PAD, phenolic acid decarboxylase; DHBD, benzoic acid decarboxylase; PAD_Mc, phenolic acid decarboxylase from Mycobacterium colombiense; 2,6-DHBD_Rs, 2,6-dihydroxybenzoic acid decarboxylase from Rhizobium sp.; 2,6-DHBA, 2,6-dihydroxybenzoic acid; PEG, poly
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Pushing the equilibrium of regio-complementary carboxylation of phenols and hydroxystyrene derivatives
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Biotechnology - Volume 168, Issue 3, November 2013, Pages 264–270
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
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Price after discount Only $4.95
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Full-text PDF Download
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Any Questions? feel free to contact us