L-蛋氨酸类似物L-2-氨基-4-叠氮基丁酸的合成

Synthesis of L-2-amino-4-azidobutanoic acid as an analogue of L-methionine

目的优化L-2-氨基-4-叠氮基丁酸的合成工艺。方法以L-蛋氨酸为起始原料经硫甲基化、水解一锅法制得L-2-氨基-4-羟基丁酸(2),2在浓盐酸中环合得到重要中间体α-氨基-γ-丁内酯盐酸盐(3),3经溴代开环、成酯、叠氮化、水解4步反应得到目标产物。结果与结论以L-蛋氨酸为起始原料,经6步反应合成目标产物,其结构经1H-NMR和IR谱确证。该合成方法原料易得、条件温和、操作简单、易于中试放大。

L-2-amino-4-azidobutanoic acid（1） as an important analogue of L-methionine is widely used in the structure modification of the protein and polypeptide.Here a route using L-methionine as starting material was established via S-methylation,hydrolysis,cyclization to provide α-amino-γ-butyrolactone hydrochloride,following by a four-step procedure as cleavage,esterification,azidonation and deprotection to synthesize L-2-amino-4-azidobutanoic acid.And its structure was confirmed by 1H-NMR and IR.The process is suitable for larger-scale preparation for its advantages of mild reaction conditions,facile operation and relatively lower cost.