The effect of boronic acid-positioning in an optical glucose-sensing ensemble

被引：65

作者：

Gamsey, Soya

Baxter, Nichol A.

Sharrett, Zachary

Cordes, David B.

Olmstead, Marilyn M.

Wessling, Ritchie A.

Singaram, Bakthan ^{[1
]}

机构：

[1] Univ Calif Santa Cruz, Dept Chem & Biochem, Santa Cruz, CA 95064 USA

[2] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

来源：

TETRAHEDRON | 2006年 / 62卷 / 26期

关键词：

boronic acid; glucose detection; fluorescence; pK(a); viologen; pyranine; saccharide sensor;

D O I：

10.1016/j.tet.2006.04.047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The quenching of the anionic dye 8-hydroxypyrene-1,3,6-trisulfonic acid trisodium salt (pyranine) with three different boronic acid-substituted benzyl viologens was determined, and the fluorescence signal modulation obtained upon addition of glucose to the dye/quencher system was also studied. The benzyl viologen that contains boronic acids in the ortho-position (o-BBV) was found to display unique behavior, which can be rationalized by a charge neutralization mechanism facilitated by an intramolecular interaction between sp(3) boronate and the quaternary nitrogen of the viologen. Potentiometric titration and B-11 NMR spectroscopy were used to generate pH profiles for the boronic acids, which provide additional evidence for the proposed mechanism. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：6321 / 6331

页数：11

共 71 条

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