Synthesis ( IF 2.2 ) Pub Date : 2020-08-06 , DOI: 10.1055/s-0040-1707223 Alfredo Vázquez 1 , Edgar Bonilla-Reyes 1 , Adrian Sánchez-Carrillo 2
Abstract
l-Kynurenine, a non-proteinogenic amino acid, is the primary metabolite of tryptophan via the kynurenine pathway. Kynurenine is involved in a variety of biological processes occurring in the human body, notably in the central nervous system. Thus, the study of this molecule offers multiple opportunities for drug discovery; however, an essential prelude for biological studies is to secure the supply of kynurenine and analogues thereof. A simple synthetic procedure for the efficient preparation of enantiomerically pure l-kynurenine from l-aspartic acid and its implementation to prepare homo-l-kynurenine from l-glutamic acid is presented. The approach relies on a photochemical aza-Fries rearrangement of the corresponding acyl-aniline as the fundamental transformation.
中文翻译:
氮杂-弗里斯重排合成1-Kynurenine和H-1-kynurenine
摘要
1 -Kynurenine是一种非蛋白氨基酸,是通过Kynurenine途径的主要色氨酸代谢产物。Kynurenine参与人体发生的各种生物过程,特别是中枢神经系统。因此,对该分子的研究为药物发现提供了多种机会。然而,生物学研究的基本前奏是确保犬尿氨酸及其类似物的供应。为对映体纯的有效制剂的简单合成方法升-kynurenine从1-天冬氨酸和其实施,以制备均聚物升从-kynurenine升存在谷氨酸。该方法依赖于相应的酰基苯胺的光化学氮杂-弗里斯重排作为基本转化。