对-二苯氨基联二苯基硼酸对单糖的识别研究  

The Discrimination of Monosaccharides by 4′-Diphenylamino-4-(1,1′-biphenyl) Boronic Acid

作　　者：周萍[1,2] 王仲如[1] 程哲[1] 张彩红[1] 双少敏[1] 

机构地区：[1]山西大学化学化工学院,山西太原030006 [2]太原理工大学轻纺工程与美术学院,山西榆次030600

出　　处：《分析科学学报》2009年第1期31-35,共5页Journal of Analytical Science

基　　金：国家自然科学基金(No.90813018);山西省自然科学基金

摘　　要：本文以二苯基胺和对-二溴联苯合成新型硼酸衍生物对-二苯氨基联二苯基硼酸(DBBA)。用DBBA作为荧光探针,在20%的乙醇水溶液中对各种单糖,如果糖、半乳糖、葡萄糖、甘露糖等进行识别研究,并且计算了DBBA与各种单糖的结合常数。研究结果表明,该新型硼酸衍生物对果糖具有很好的选择性识别。初步探讨了DBBA与果糖、半乳糖、葡萄糖、甘露糖的识别机理,表明DBBA能够识别单糖,DBBA具有分子内电荷转移特性,它与单糖分子结合后不同程度地阻碍了其分子内的电荷转移性质。A novel boronic acid fluorescence probe, 4′-diphenylamino-4-（1, 1′-biphenyl） boronic acid （DBBA）, was synthesized with diphenylamine and 4,4′-dibromobiphenyl as material. The probe was used to recognize several saccharides （such as fructose, galactose, glucose and mannose, et al. ） in 20% （V/V） ethanol aqueous, and the binding constants of DBBA with all the selected saccharides were determined. The results suggested that this novel boronate has substantial selectivity to fructose. The mechanisms of these recognition process were also explored, and the results demonstrated that the recognization of monosaccharides by DBBA was based on the twisted intramolecular electron transfer （TICT）, and DBBA binding with various monosaccharides could induce different degree of inhibition to the TICT system.

关 键 词：对-二苯氨基联二苯基硼酸 果糖 半乳糖 葡萄糖 甘露糖 荧光探针 

分 类 号：O657.39[理学—分析化学]