Suzuki homo-coupling reaction based fluorescent sensors for monosaccharides

Su-Ying Xu,Hui-Chen Wang,Yun-Bao Jiang,Tony D James,Stephen E Flower,John S Fossey

doi:10.1039/c4ra07331b

Su-Ying Xu, Hui-Chen Wang + Show 4 more

Open Access

https://doi.org/10.1039/c4ra07331b

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Abstract

Palladium catalysed, aryl boronic acid homocoupling, is explored as a fluorescence sensing regime for saccharides. The catalytic formation rate of fluorescent bi-aryls, under control of a palladium catalyst, is modulated by the presence of saccharides. The nature of the aryl group, rate of biaryl formation and limits of detection are investigated.

Highlights

Saccharide recognition is vital to the development and survival of life and has attracted signi cant interest.[1,2,3,4,5] the development of synthetic, saccharide recognition domains that can compete with bulk water to recognise these heavily solvated saccharide molecules remains a challenging problem.[6,7,8] Aryl boronic acids reversibly bind covalently with 1,2- and 1,3-diols to form ve- and six-member boronate esters, respectively (Fig. 1).The reversible covalent binding of boronic acids with saccharides has been extensively explored in the area of directNew chemosensing strategies with enhanced sensitivity are in great demand
In previous work by some of the authors included in this report, the palladium catalysed formation of biphenyl via a homocoupling of phenylboronic acid was used as a probe to detect saccharide binding.[18]
The approach relies on the catalytic formation of the reporter molecule, the sensitivity is not limited to the detection of the added probe rather the formation of biphenyl giving enhanced opportunities for sensitivity in colorimetric and uorometric sensing, since the background and noise are minimised

Summary

Introduction

Saccharide recognition is vital to the development and survival of life and has attracted signi cant interest.[1,2,3,4,5] the development of synthetic, saccharide recognition domains that can compete with bulk water to recognise these heavily solvated saccharide molecules remains a challenging problem.[6,7,8] Aryl boronic acids reversibly bind covalently with 1,2- and 1,3-diols to form ve- and six-member boronate esters, respectively (Fig. 1).The reversible covalent binding of boronic acids with saccharides has been extensively explored in the area of directNew chemosensing strategies with enhanced sensitivity are in great demand. Aryl boronic acid homocoupling, is explored as a fluorescence sensing regime for saccharides.

Results

Conclusion