A competition assay for determining glucose-6-phosphate concentration with a tris-boronic acid receptor

Cabell, Larry A.; Monahan, Mary Katherine; Anslyn, Eric V.

doi:10.1016/s0040-4039(99)01651-2

Cited by 88 publications

(42 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Sensing ensembles such as these have been developed for a wide range of analytes including chiral diols [68], the anticoagulant oligosaccharide heparin [86], phosphosugars [12], nucleotides [84] and more [41,54,56,83].…”

Section: Displacement Assays As a Measure Of Enzyme Activitymentioning

confidence: 99%

Molecular recognition with boronic acids—applications in chemical biology

2013

View full text Add to dashboard Cite

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.

show abstract

Section: Displacement Assays As a Measure Of Enzyme Activitymentioning

confidence: 99%

Molecular recognition with boronic acids—applications in chemical biology

2013

View full text Add to dashboard Cite

show abstract

“…17 Thus, glucose-6-phosphate receptor 10 incorporates three m-aminomethyl benzene boronic acids as the binding sites on the 1,3,5-trisubstituted-2,4,6-triethylbenzene scaffold. 18 The boronic acids are in a position to form cyclic boronate esters with the hydroxyls of glucose-6-phosphate, while the ammoniums were incorporated to coordinate with the phosphate through charge pairing interactions. It is worth noting here that the kinetics of the boronate ester formation is fast in a basic environment when the boron is tetrahedral.…”

Section: Glucose-6-phosphate Sensing Ensemblementioning

confidence: 99%

Teaching Old Indicators New Tricks

et al. 2001

Self Cite

View full text Add to dashboard Cite

Most synthetic sensors are designed with covalent attachment between a receptor and a reporter moiety. In this report, we describe the current progress of our use of noncovalently attached indicators to signal binding of analytes. With these systems, analyte binding leads to indicator displacement from the binding cavity, which in turn yields an optical signal modulation. We include previous examples, the strategies involved in our development, and the advantages as well as disadvantages of this method. Finally, our latest research in this field is briefly presented.

show abstract

“…At low pH values, boronic acids 1 a-d exist in the neutral trigonal form, 1, with a possible BÀN bond through donation of the nitrogen lone-pair electrons to the boron open shell. [40,41,43,71] It is understood that the aromatic amine group involved is not a strong Lewis base because of the substitution of two electron-withdrawing imide functional groups on the naphthalene ring. Therefore, the exact strength (or existence) of the B À N bond is not clear.…”

Section: à4mentioning

confidence: 99%

Synthesis, Evaluation, and Computational Studies of Naphthalimide‐Based Long‐Wavelength Fluorescent Boronic Acid Reporters

Jin

Wang

et al. 2008

Chemistry A European J

View full text Add to dashboard Cite

Boronic acids that change fluorescence properties upon sugar binding are very useful for the synthesis of carbohydrate sensors. Along this line, boronic acids that fluoresce beyond 500 nm are especially useful. A series of boronic acid fluorescent reporter compounds based on the 4-amino-1,8-naphthalimide structure have been synthesized (1a-d) and evaluated under near physiological conditions. These compounds showed good water solubility and significant changes in fluorescence properties after binding with sugars, with the emission wavelength being at around 570 nm. Analogues in this series with different substitutions showed similar properties. We have also examined the mechanism of the observed fluorescence changes for these compounds.

show abstract

A competition assay for determining glucose-6-phosphate concentration with a tris-boronic acid receptor

Cited by 88 publications

References 17 publications

Molecular recognition with boronic acids—applications in chemical biology

Molecular recognition with boronic acids—applications in chemical biology

Teaching Old Indicators New Tricks

Synthesis, Evaluation, and Computational Studies of Naphthalimide‐Based Long‐Wavelength Fluorescent Boronic Acid Reporters

Contact Info

Product

Resources

About