Electrochemical Amination Reactions for Amino Acid Synthesis

这项小型企业创新研究（SBIR）的总体目的是为氨基酸的商业生产开发一种有效的电化学过程。I期项目的重点是确定两种电化学胺化反应的技术可行性，以生产dl-多巴（用于制备人造甜味剂Nutrasweet）和dl-苯丙氨酸（用于治疗老年帕金森病）。所做的工作证明了这种氨基酸合成途径生产dl外消旋混合物的可行性。这个第二阶段的努力将指向合成光学活性氨基酸使用聚合物衍生电极。另外两种商业上重要的氨基酸将被合成，l-丙氨酸和l-缬氨酸。第二阶段的具体技术重点将包括：o将Ti3+/Ti4+氧化还原偶对结合到聚合物衍生电极中，以实现氨基自由基形成的高法拉第效率。o在聚合物衍生电极上提供光学活性位点，用于在靠近电极/电解质界面区域进行胺化的前体分子中诱导光学活性。o使用第二阶段优化的电极组件和实验条件制备和电化学测试原型电解电池。应用电有机合成技术制备特种化学品比传统的化学合成路线具有以下优点：提供比同等化学过程更大的选择性，对环境更无害，并提供简化整体工业过程的机会，其中可以避免在传统化学过程中通常发现的一个或多个步骤。这项研究也将增加对电化学反应机理和电解电池的理解。

The overall purpose of this Small Business Innovation Research (SBIR) is to develop an efficient electrochemical process for the commercial production of amino acids. Emphasis of the Phase I program was directed towards determining the technical feasibility of two electrochemical amination reactions to produce dl-dopa (used in the preparation of the artificial sweetener Nutrasweet) and dl-phenylalanine (used in the treatment of Parkinson's Disease in the elderly). Work performed demonstrated the viability of this amino acid synthesis route to produce dl racemic mixtures. This Phase II effort will be directed towards the synthesis of optically active amino acids using polymer derivatized electrodes. Two additional commercially important amino acids will be synthesized, l-alanine and l-valine. Specific technical emphasis during Phase II will include: o Incorporating the Ti3+/Ti4+ redox couple into polymer derivatized electrodes to achieve high Faradaic efficiencies for aminyl radical formation. o Providing optically active sites on the polymer derivatized electrode for inducing optical activity in the precursor molecule subject to amination in close proximity to the electrode/electrolyte interfacial region. o Preparing and electrochemically testing prototype electrolytic cells using electrode components and experimental conditions optimized during Phase II. The application of electroorganic synthesis technology for the preparation of specialty chemicals can have advantages over conventional chemical synthesis routes including: providing greater selectivity than an equivalent chemical process, being environmentally more benign, and providing the opportunity for a simplified overall industrial process where one or more steps normally found in conventional chemical processes can be avoided. The research will also increase understanding of electrochemical reaction mechanisms and electrolytic cells.