To address the growing need for removing the emerging endocrine disrupting compounds (EDCs), the enzyme-based oxidative coupling reaction is suggested as promising alternative in consideration of its generally high specificity and removal efficiency on treatment of waters containing estrogenic phenolic chemicals. udVarious factors that affect the reaction rate of oxidative coupling (OXC) reaction of phenolic estrogens catalyzed by Horseradish Peroxidase (HRP) were evaluated in this study. Kinetic parameters were obtained for the removal of phenol as well as natural and synthetic estrogens estrone (E1), 17β-estradiol (E2), estriol (E3), and 17α-ethinylestradiol (EE2). Molecular orbital theory and Autodock software were employed to analyze chemical properties and substrate binding characteristics. It is found that the reactions were first order with respect to phenolic concentration and reaction rate constants (kr) were determined for phenol, E3, E1, E2 and EE2 (in increasing order). It is also found that oxidative coupling was controlled by enzyme-substrate interactions, not diffusion. Docking simulations show that higher binding energy and shorter binding distance both promote more favorable kinetics. This research is the first to show that the OXC of phenolics is an entropy-driven and enthalpy-retarded process.ud
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机译：为了满足对去除新兴的内分泌干扰化合物（EDC）的日益增长的需求，鉴于基于酶的氧化偶联反应在处理含有雌激素酚类化合物的水中通常具有很高的特异性和去除效率，因此被认为是有前途的替代方法。本研究评估了影响辣根过氧化物酶（HRP）催化的酚类雌激素的氧化偶联（OXC）反应速率的各种因素。获得了用于去除苯酚以及天然和合成雌激素雌酮（E1），17β-雌二醇（E2），雌三醇（E3）和17α-炔雌醇（EE2）的动力学参数。采用分子轨道理论和Autodock软件分析化学性质和底物结合特性。发现该反应相对于酚类浓度是一阶的，并且确定了苯酚，E3，E1，E2和EE2的反应速率常数（kr）（升序）。还发现氧化偶合是由酶-底物相互作用而不是扩散控制的。对接模拟表明，较高的结合能和较短的结合距离均促进了更有利的动力学。这项研究是第一个表明酚醛树脂的OXC是一种由熵驱动且受焓延迟的过程。 ud
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