由芳香族氨基酸直接合成α-硫代芳香酸。
Direct Synthesis of α-Thio Aromatic Acids from Aromatic Amino Acids.
作者信息
Samuels Eric R, Sevrioukova Irina
机构信息
Department of Pharmaceutical Sciences, University of California, Irvine, California 92697-3900.
Department of Molecular Biology and Biochemistry, University of California, Irvine, California 92697-3900.
出版信息
Tetrahedron Lett. 2018 Mar 21;59(12):1140-1142. doi: 10.1016/j.tetlet.2018.02.030. Epub 2018 Feb 13.
Abstract
Modified amino acids are useful synthetic components in both chemistry and biology. Here we describe a simple, scalable two-step procedure to generate α-thio aromatic acids from aromatic amino acids with yields of up to 96%. Diazotization and α-lactone mediated bromination efficiently form the α-bromo acid with retention of configuration. Thiol substitution with mild reagents such as sodium hydrosulfide or sodium trithiocarbonate provides the inverted, free α-thio acid. The mildly acidic soft nucleophile can then be utilized in many synthetic applications.
摘要
修饰氨基酸在化学和生物学领域都是有用的合成成分。在此，我们描述了一种简单、可扩展的两步法，用于从芳香族氨基酸生成α-硫代芳香酸，产率高达96%。重氮化和α-内酯介导的溴化反应能有效地形成具有构型保留的α-溴代酸。用温和的试剂如硫化氢钠或三硫代碳酸钠进行硫醇取代，可得到构型翻转的游离α-硫代酸。然后，这种温和酸性的软亲核试剂可用于许多合成应用中。
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