L-7-羟基香豆素氨基酸衍生物的合成及其性能  

Synthesis and Properties of L-7-Hydroxyl Coumarin Amino Acid Derivatives

作　　者：喻思思 官召兵 杨蕾 胡晓松 YU Si-si;GUAN Zhao-bing;YANG Lei;HU Xiao-song(Chemical Engineering and Life Sciences,Wuhan University of Technology,Wuhan 430070,China)

机构地区：[1]武汉理工大学化学化工与生命科学学院,湖北武汉430070

出　　处：《合成化学》2018年第8期572-576,共5页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金面上项目(21472144)

摘　　要：以保护L-谷氨酸(2)为原料,与N,N'-羰基二咪唑反应制得化合物3;3与丙二酸单乙酯镁盐反应制得β-酮酯(4);4分别与4-氟间苯二酚和4-氯间苯二酚进行Pechmann缩合后,在酸中脱除保护基合成了L-7-羟基香豆素氨基酸(1a)及其两个衍生物(1b,35.3%和1c,40.6%),其结构经1H NMR,13C NMR和HR-MS(ESI)确证。采用UV-Vis研究了1b和1c的p Ka。结果表明:1b和1c的p Ka分别为6.21和6.14。两个衍生物的荧光性能与pH密切相关。Compound 3 was obtained by the reaction of protected L-glutamic acid（ 2） with 1,1＇-carbonyldiimidazole. β-Ketoester（ 4） was afforded by condensation of 3 with ethyl magnesium malonate.Two derivatives（ 1 b,35. 3%; 1 c,40. 6%） of L-7-hydroxycoumarin amino acid（ 1 a） was synthesized by Pechmann condensation of 4 with 4-fluoro resorcinol or 4-chloro resorcinol,then deprotection in acid. The structures were confirmed by ~1H NMR,^（13）C NMR and HR-MS（ ESI）. PKa of 1b and 1c were investigated by UV-Vis. The results showed that the pKa of 1b and 1c were 6. 21 and 6. 14,respectively. The fluorescent spectroscopy of 1b and 1c had a close relationship with pH.

关 键 词：L-谷氨酸 香豆素氨基酸 荧光探针 合成 荧光性能 

分 类 号：O621.3[理学—有机化学] O657.3[理学—化学]