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钴胺素介导的氯乙酸乙酯在二甲基甲酰胺中的电催化还原反应

Cobalamin-Mediated Electrocatalytic Reduction of Ethyl Chloroacetate in Dimethylformamide.

作者信息

Gerroll Benjamin H R, Lewis Jared C, Baker Lane A

机构信息

Department of Chemistry, Indiana University Bloomington, Indiana 47405, United States.

Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States.

出版信息

J Electrochem Soc. 2022 May;169(5). doi: 10.1149/1945-7111/ac6a13. Epub 2022 May 4.

DOI:10.1149/1945-7111/ac6a13
PMID:35812015
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9265244/
Abstract

The catalytic reduction of ethyl chloroacetate (ECA) by hydroxocobalamin (HOCbl) in dimethylformamide was studied electrochemically and spectroelectrochemically to identify initial steps in the reaction between the electrogenerated Co(I) center of cobalamin (cob(I)alamin) and ECA. Cyclic voltammograms of HOCbl in the presence of ECA show a small increase in current related to reduction of Co(II) to Co(I), and a new peak at more negative potentials related to reduction of an ethyl carboxymethyl-Cbl intermediate. The oxidation state of HOCbl during catalysis was monitored by means of spectroelectrochemical controlled-potential bulk electrolysis. Addition of ECA to electrogenerated cob(I)alamin initially generates the Co(II) form (cob(II)alamin) followed by a gradual formation of an ethyl carboxymethyl-Cbl intermediate. Controlled-potential bulk electrolysis was performed to identify products formed from catalytic reduction of ECA by electrogenerated cob(I)alamin and quantify the number of electrons transferred per molecule of ECA. Product distributions and coulometric results, together with the results of voltammograms and spectroelectrochemical controlled-potential bulk electrolysis, were interpreted to propose a reaction mechanism.

摘要

在二甲基甲酰胺中，用电化学和光谱电化学方法研究了羟钴胺素（HOCbl）对氯乙酸乙酯（ECA）的催化还原反应，以确定钴胺素（钴胺素（I））的电生成Co（I）中心与ECA之间反应的初始步骤。在存在ECA的情况下，HOCbl的循环伏安图显示，与Co（II）还原为Co（I）相关的电流略有增加，并且在更负的电位处出现一个新峰，与乙基羧甲基-Cbl中间体的还原有关。通过光谱电化学控制电位本体电解监测催化过程中HOCbl的氧化态。将ECA添加到电生成的钴胺素（I）中，最初生成Co（II）形式（钴胺素（II）），随后逐渐形成乙基羧甲基-Cbl中间体。进行控制电位本体电解，以鉴定电生成的钴胺素（I）对ECA催化还原形成的产物，并量化每分子ECA转移的电子数。对产物分布和电量分析结果，以及伏安图和光谱电化学控制电位本体电解的结果进行了解释，以提出反应机理。