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首页> 外文期刊>The FEBS journal >Biocatalytic carboxylation of phenol derivatives: kinetics and thermodynamics of the biological Kolbe-Schmitt synthesis
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Biocatalytic carboxylation of phenol derivatives: kinetics and thermodynamics of the biological Kolbe-Schmitt synthesis

机译：苯酚衍生物的生物催化羧化：生物学Kolbe-Schmitt合成的动力学和热力学

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摘要

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.
机译：微生物脱羧酶在厌氧解毒途径中催化酚类衍生物的可逆区域选择性原羧化反应，已经研究了它们在富电子芳族底物上的反向羧化活性。邻羟基苯甲酸是化学和制药工业中的重要组成部分，目前是通过Kolbe-Schmitt工艺生产的，该工艺需要较高的压力和温度（5bar，100摄氏度），并且通常显示出不完全的区域选择性。为了解决制备规模应用中的瓶颈，我们研究了根瘤菌（Rhizobiumsp）2,6-二羟基苯甲酸脱羧酶的动力学参数。以1，2-二羟基苯（邻苯二酚）为起始原料在羧基化和脱羧方向上进行。根据可逆的随机双-单机理，通过Haldane方程，催化性能（K-m，V-max）与整体热力学平衡相关。随后通过将实验结果与仿真结果进行比较来验证该模型。这项研究提供了对非氧化性芳族脱羧酶催化行为的见解，并揭示了关键的局限性（例如底物氧化，CO2压力，酶失活，低周转频率），因为该系统可作为Kolbe-Schmitt的替代品流程。

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