Recognition of phospho sugars and nucleotides with an array of boronic acid appended bipyridinium salts

Schiller, Alexander; Vilozny, Boaz; Wessling, Ritchie A.; Singaram, Bakthan

doi:10.1016/j.aca.2008.08.011

Cited by 39 publications

(57 citation statements)

References 42 publications

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“…Each analyte will have its own specific pattern of displacement, and in this way, complex mixtures can be deconvoluted. These sensing systems have been developed for many saccharide mixtures including monosaccharides and saccharide derivatives [16,23], ginsenosides [85] and nucleotides [66].…”

Section: Multicomponent Sensing Of Saccharide-containing Medicationsmentioning

confidence: 99%

Molecular recognition with boronic acids—applications in chemical biology

2013

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Small molecules have long been used for the selective recognition of a wide range of analytes. The ability of these chemical receptors to recognise and bind to specific targets mimics certain biological processes (such as proteinsubstrate interactions) and has therefore attracted recent interest. Due to the abundance of biological molecules possessing polyhydroxy motifs, boronic acids-which form fivemembered boronate esters with diols-have become increasingly popular in the synthesis of small chemical receptors. Their targets include biological materials and natural products including phosphatidylinositol bisphosphate, saccharides and polysaccharides, nucleic acids, metal ions and the neurotransmitter dopamine. This review will focus on the many ways in which small chemical receptors based on boronic acids have been used as biochemical tools for various purposes, including sensing and detection of analytes, interference in signalling pathways, enzyme inhibition and cell delivery systems. The most recent developments in each area will be highlighted.

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Section: Multicomponent Sensing Of Saccharide-containing Medicationsmentioning

confidence: 99%

Molecular recognition with boronic acids—applications in chemical biology

2013

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“…Not surprisingly, it has found application in the sensing of various analytes including cations [70][71][72], anions [73], electroneutral small molecules such as amino acids [74], saccharides [75,76], explosives [77], poisonous gases [78], peptides [79] and proteins [80,81], consumer products including sweeteners [82], beverages [26,70,83], and toothpastes [73], and so on.…”

Section: Principal Component Analysismentioning

confidence: 99%

“…These include samples and analyses of beverages [83,83] sweeteners [82], saccharides [76,91] and oligosaccharides [92], amines [93], and other analytes.…”

Section: Hierarchical Clustering Analysis (Hca)mentioning

confidence: 99%

“…It was used in a variety of settings and media including solutions, vapors, or solid-liquid interfaces such as in molecularly imprinted polymers [94]. The analytes classified range from small ions and molecules, saccharides [76,95], amines [96,97], explosives [98,99], peptides to evaluate peptide phosphorylation [100], and many others. In the arena of biorecognition, LDA was used with enormous success.…”

Section: Supervised Pattern Recognition and Linear Discriminant Analymentioning

confidence: 99%

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Array‐Based Sensors

Anzenbacher

Palacios

2011

Chemosensors

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“…[17] In combination with salt bridges and hydrogen bonding, sensing ensembles using boronic acids have been developed for citrate, [18] tartrate, [19,20] malate, [20] gallate, [21] glucose-6-phosphate, [22,23] inositol-1, 4, 5-trisphosphate, [24] and heparin. [25] Singarams group [26] reported an array of boronic acid-appended bipyridinium salts for the recognition of phosphor-sugars and nucleotides, but the discrimination of large natural products, such as ginsenosides, has not yet been achieved. [27] We recently reported a porphyrin-bisboronic acid scaffold for the sensing of ginsenosides with the prophyrin as a signaling unit.…”

Section: Introductionmentioning

confidence: 99%

Discrimination and Classification of Ginsenosides and Ginsengs Using Bis‐Boronic Acid Receptors in Dynamic Multicomponent Indicator Displacement Sensor Arrays

Zhang¹,

You²,

Anslyn³

et al. 2011

Chemistry A European J

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Ginsenosides are complex natural products with a diverse array of biological activities, but their molecular recognition and sensing is challenging. A library of simple bis-boronic acid-based receptors with various spacers was synthesized for the sensing of ginsenosides. The incorporation of two boronic acids allowed the pairing of two indicators, which can simultaneously bind the receptors or two saccharides within the ginsenosides. A cross-reactive sensing array was therefore constructed using the receptors in conjunction with different pairs of indicators. LDA plots created from the colorimetric response of the hosts and indicator pairs reveal excellent classification of the ginsenosides, and the corresponding loading plots reveal the cross-reactivity of the receptors. In addition, several commercial ginseng extracts were unambiguously classified using the same sensing array. The assay reported here should be applicable to the analysis of other large saccharide-based natural products.

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Recognition of phospho sugars and nucleotides with an array of boronic acid appended bipyridinium salts

Cited by 39 publications

References 42 publications

Molecular recognition with boronic acids—applications in chemical biology

Molecular recognition with boronic acids—applications in chemical biology

Array‐Based Sensors

Discrimination and Classification of Ginsenosides and Ginsengs Using Bis‐Boronic Acid Receptors in Dynamic Multicomponent Indicator Displacement Sensor Arrays

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