Department of Pharmaceutical Sciences, College of Pharmacy and Pharmaceutical Sciences, Washington State University, Spokane, WA, 99201, United States.
Department of Pharmaceutical Sciences, College of Pharmacy and Pharmaceutical Sciences, Washington State University, Spokane, WA, 99201, United States.
Anal Biochem. 2020 Oct 15;607:113862. doi: 10.1016/j.ab.2020.113862. Epub 2020 Aug 6.
α-Ketoglutaramic acid (KGM, α-ketoglutaramate), also known as 2-oxoglutaramic acid (OGM, 2-oxoglutaramate), is a substrate of ω-amidase, also known as Nitrilase 2 (NIT2), and is essential for studying the canonical role of ω-amidase, as well as its role in multiple diseases. Until now, KGM used for biological studies has been prepared most often by the enzymatic oxidation of l-glutamine using snake venom l-amino acid oxidase, which provides KGM as an aqueous solution, containing by-products including 5-oxoproline and α-ketoglutarate. The enzymatic method for KGM preparation, therefore, cannot provide pure product or an accurate percent yield evaluation. Here, we report a synthetic method for the preparation of this important substrate, KGM, in 3 steps, from l-2-hydroxyglutaramic acid, in pure form, in 53% overall yield.
α-酮戊二酸（KGM，α-酮戊二酸盐），也称为 2-氧代戊二酸（OGM，2-氧代戊二酸盐），是ω-酰胺酶的底物，也称为腈酶 2（NIT2），是研究ω-酰胺酶的典型作用以及其在多种疾病中的作用的必要条件。到目前为止，用于生物学研究的 KGM 最常通过蛇毒 l-氨基酸氧化酶对 l-谷氨酰胺进行酶促氧化来制备，该方法提供 KGM 作为水溶液，包含副产物包括 5-氧代脯氨酸和α-酮戊二酸。因此，酶法制备 KGM 无法提供纯产物或准确的产率评估。在这里，我们报告了一种从 l-2-羟基戊二酸出发，经 3 步反应，以纯形式制备这种重要底物 KGM 的合成方法，总收率为 53%。
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