Zhang Yanling, Gao Xingming, Hardcastle Kenneth, Wang Binghe
Department of Chemistry and Center for Biotechnology and Drug Design, Georgia State University, Atlanta, GA 30302-4089, USA.
Chemistry. 2006 Feb 1;12(5):1377-84. doi: 10.1002/chem.200500982.
Four new naphthalene-based boronic acid compounds (1-4) were synthesized. The effect of various carbohydrates on their fluorescence properties has been studied in aqueous phosphate buffer at pH 7.4. Different substitutions on the aniline group of the naphthalene ring resulted in significant differences in fluorescence properties for these four compounds. Compound 1 shows ratiometric fluorescence changes upon addition of a sugar. Compounds 2 and 3 do not show ratiometric fluorescence changes but show very large fluorescence intensity changes (about 70-fold fluorescence intensity increase). In addition to the quantifiable fluorescence property changes upon sugar addition, the fluorescence color changes of 1-3 are also visible to the naked eye. However, amidation of the aniline nitrogen atom significantly diminishes the fluorescence intensity of compound 4. The crystal structure of one boronic acid provided some insight into the structural features that are important for the fluorescence properties of these compounds.
合成了四种新型萘基硼酸化合物（1 - 4）。在pH 7.4的磷酸盐水溶液中研究了各种碳水化合物对其荧光性质的影响。萘环上苯胺基团的不同取代导致这四种化合物的荧光性质存在显著差异。化合物1在添加糖后显示出比率荧光变化。化合物2和3不显示比率荧光变化，但显示出非常大的荧光强度变化（荧光强度增加约70倍）。除了添加糖后可量化的荧光性质变化外，1 - 3的荧光颜色变化肉眼也可见。然而，苯胺氮原子的酰胺化显著降低了化合物4的荧光强度。一种硼酸的晶体结构为这些化合物荧光性质的重要结构特征提供了一些见解。
