Literature DB >> 17927178

Boronic acid based peptidic receptors for pattern-based saccharide sensing in neutral aqueous media, an application in real-life samples.

Nicola Y Edwards1, Thomas W Sager, John T McDevitt, Eric V Anslyn.   

Abstract

The advent of the alternative sweeteners market has signaled a demand for chemosensors which target multiple saccharides and saccharide derivatives, in aqueous media at physiological pH. This demand has largely been unmet as existing molecular receptors for saccharides have generally not shown sufficient degrees of affinity and selectivity in aqueous media. A chemosensor array for saccharides and saccharide derivatives, fully operational in aqueous media at physiological pH, has been developed and is reported herein. Boronic acid based peptidic receptors, derived from a combinatorial library, served as the cross-reactive sensor elements in this array. The binding of saccharides to these receptors was assessed colorimetrically using an indicator uptake protocol in the taste-chip platform. The differential indicator uptake rates of these receptors in the presence of saccharides were exploited in order to identify patterns within the data set using linear discriminant analysis. This chemosensor array is capable of classifying disaccharides and monosaccharides as well as discriminating compounds within each saccharide group. Disaccharides have also been distinguished from closely related reduced-calorie counterparts. This linear discriminant analysis set was then employed as a training set for identifying a specific saccharide in a real-world beverage sample. The methodology developed here augurs well for use in other real-world samples involving saccharides as well as for sensing other desired analytes.

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Year:  2007        PMID: 17927178     DOI: 10.1021/ja073939u

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  28 in total

Review 1.  Single-walled carbon nanotube-based near-infrared optical glucose sensors toward in vivo continuous glucose monitoring.

Authors:  Kyungsuk Yum; Thomas P McNicholas; Bin Mu; Michael S Strano
Journal:  J Diabetes Sci Technol       Date:  2013-01-01

2.  Colorimetric detection and identification of natural and artificial sweeteners.

Authors:  Christopher J Musto; Sung H Lim; Kenneth S Suslick
Journal:  Anal Chem       Date:  2009-08-01       Impact factor: 6.986

3.  Ratiometric Array of Conjugated Polymers-Fluorescent Protein Provides a Robust Mammalian Cell Sensor.

Authors:  Subinoy Rana; S Gokhan Elci; Rubul Mout; Arvind K Singla; Mahdieh Yazdani; Markus Bender; Avinash Bajaj; Krishnendu Saha; Uwe H F Bunz; Frank R Jirik; Vincent M Rotello
Journal:  J Am Chem Soc       Date:  2016-03-23       Impact factor: 15.419

4.  Chemical functionalization of oligodeoxynucleotides with multiple boronic acids for the polyvalent binding of saccharides.

Authors:  Amanda E Hargrove; Andrew D Ellington; Eric V Anslyn; Jonathan L Sessler
Journal:  Bioconjug Chem       Date:  2011-02-07       Impact factor: 4.774

5.  Thermodynamically Controlled, Dynamic Binding of Diols to a 1,2-BN Cyclohexane Derivative.

Authors:  Gregory P Harlow; Lev N Zakharov; Gang Wu; Shih-Yuan Liu
Journal:  Organometallics       Date:  2013       Impact factor: 3.876

6.  A new class of fluorescent boronic acids that have extraordinarily high affinities for diols in aqueous solution at physiological pH.

Authors:  Yunfeng Cheng; Nanting Ni; Wenqian Yang; Binghe Wang
Journal:  Chemistry       Date:  2010-12-03       Impact factor: 5.236

7.  ICP-MS-based multiplex profiling of glycoproteins using lectins conjugated to lanthanide-chelating polymers.

Authors:  Michael D Leipold; Isaac Herrera; Olga Ornatsky; Vladimir Baranov; Mark Nitz
Journal:  J Proteome Res       Date:  2009-02       Impact factor: 4.466

Review 8.  Molecular recognition with boronic acids-applications in chemical biology.

Authors:  Gillian F Whyte; Ramon Vilar; Rudiger Woscholski
Journal:  J Chem Biol       Date:  2013-06-01

Review 9.  Carbohydrate recognition by boronolectins, small molecules, and lectins.

Authors:  Shan Jin; Yunfeng Cheng; Suazette Reid; Minyong Li; Binghe Wang
Journal:  Med Res Rev       Date:  2010-03       Impact factor: 12.944

10.  A colorimetric sensor array for detection and identification of sugars.

Authors:  Sung H Lim; Christopher J Musto; Erwin Park; Wenxuan Zhong; Kenneth S Suslick
Journal:  Org Lett       Date:  2008-09-11       Impact factor: 6.005

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