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首页> 外文期刊>RSC Advances >Biocatalytic asymmetric Michael addition reaction of L-arginine to fumarate for the green synthesis of N-(([(4S)-4-amino-4-carboxy-butyl]amino)iminomethyl)-L-aspartic acid lithium salt (L-argininosuccinic acid lithium salt)
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Biocatalytic asymmetric Michael addition reaction of L-arginine to fumarate for the green synthesis of N-(([(4S)-4-amino-4-carboxy-butyl]amino)iminomethyl)-L-aspartic acid lithium salt (L-argininosuccinic acid lithium salt)

机译：L-精氨酸对富马酸酯的生物催化不对称迈克尔加成反应，绿色合成 N -（（[[（4 S ）-4-氨基-4-羧基-丁基]氨基）亚氨基甲基）-L-天冬氨酸锂盐（L-精氨酸琥珀酸锂盐）

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摘要

The basic natural amino acid L-argininosuccinate containing two chiral centers occurs in L-alanine, L-arginine, L-aspartate, L-glutamate and L-proline metabolic pathways and plays a role in the biosynthesis of secondary metabolites and other amino acids. It is a precursor for arginine in the urea cycle or the citrulline–NO cycle as well as a precursor to fumarate in the citric acid cycle via argininosuccinate lyase. We aimed to run part of the urea cycle in reverse by catalyzing not the elimination but the addition reaction of L-arginine to fumarate in order to synthesize L-argininosuccinate. Argininosuccinate lyase (ASL) from Saccharomyces cerevisiae has been chosen as the catalyst for this addition reaction. The selected ARG4 gene was synthesized and homogeneously expressed in E. coli leading to a highly active argininosuccinate lyase. The ASL-catalyzed addition reaction of L-arginine to fumarate has been successfully developed at gram scale. After a standard workup procedure the pure final product L-argininosuccinate has been isolated in good yield and high purity.
机译：包含两个手性中心的基本天然氨基酸 L -精氨酸琥珀酸酯出现在 L -丙氨酸， L -精氨酸， L -天门冬氨酸， L -谷氨酸和 L -脯氨酸代谢途径，在次生代谢产物和其他氨基酸的生物合成中发挥作用。它是尿素循环或瓜氨酸-NO循环中精氨酸的前体，也是柠檬酸循环中通过精氨琥珀酸裂合酶产生富马酸酯的前体。我们旨在通过催化 L -精氨酸向富马酸酯的加成反应，而不是催化消除反应，来部分逆转尿素循环，以合成 L -精氨酸琥珀酸酯。选择了来自酿酒酵母的精氨酸琥珀酸裂合酶（ASL）作为该加成反应的催化剂。合成了所选的 ARG4 基因，并在 E中均一表达。大肠杆菌导致高度活跃的精氨琥珀酸裂合酶。在克级成功开发了ASL催化的 L -精氨酸与富马酸酯的加成反应。经过标准的后处理程序，以高收率和高纯度分离出纯净的最终产物 L -精氨酸琥珀酸酯。

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