NOVEL SACCHARIDE-PHOTOINDUCED ELECTRON-TRANSFER SENSORS BASED ON THE INTERACTION OF BORONIC ACID AND AMINE
NOVEL SACCHARIDE-PHOTOINDUCED ELECTRON-TRANSFER SENSORS BASED ON THE INTERACTION OF BORONIC ACID AND AMINE
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DOI：
10.1021/ja00140a013
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发表时间：
1995-09-06
影响因子：
15
通讯作者：
SHINKAI, S
中科院分区：
文献类型：
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作者：
JAMES, TD;SANDANAYAKE, KRAS;SHINKAI, S
合成了两种硼酸体系，单硼酸3和二硼酸8。当β-氨基甲酸与这些硼酸形成环状硼酸酯时，硼酸部分与叔胺之间的刘易斯酸碱相互作用增强;当β-氨基甲酸与硼酸形成环状硼酸酯时，硼酸的酸性增强。这种酸碱相互作用的强度调节从胺到蒽的光诱导电子转移（PET）。这两种化合物在pH 7.77下通过抑制糖结合时从氮到蒽的光诱导电子转移而显示出增加的荧光，这是更强的硼-氮键的直接结果。化合物3显示了单硼酸对H2O的典型选择性。具有裂缝状结构的化合物8对葡萄糖具有特别的选择性和敏感性，这是由于在两种硼酸与葡萄糖的1，2-和4，6-羟基之间形成分子内1：1复合物。这是在PET传感器系统中实现单糖的双位识别的第一个例子。
Two boronic acid systems, monoboronic acid 3 and diboronic acid 8, were synthesized. When saccharides form cyclic boronate esters with these boronic acids, the Lewis acid-base interaction between the boronic acid moiety and tertiary amine is strengthened; when saccharides form cyclic boronate esters with boronic acids the acidity of the boronic acid is enhanced. The strength of this acid-base interaction modulates the photoinduced electron transfer (PET) from the amine to anthracene. Both of these compounds show increased fluoresecence at pH 7.77 through supression of the photoinduced electron transfer from nitrogen to anthracene on saccharide binding, a direct result of the stronger boron-nitrogen bond. Compound 3 shows the typical selectivity of monoboronic acids towards saccharides. Compound 8 which has a cleftlike structure is particularly selective and sensitive for, glucose due to the formation of an intramolecular 1:1 complex between the two boronic acids and the 1,2- and 4,6-hydroxyls of glucose. This is the first example in which ditopic recognition of monosaccharides is achieved in a PET sensor system.