Stereochemical and Regiochemical Trends in the Selective Detection of Saccharides

Jiang, Shan; Escobedo, Jorge O.; Kim, Kyu Kwang; Alptürk, Onur; Samoei, George K.; Fakayode, Sayo O.; Warner, Isiah M.; Rusin, Oleksandr; Strongin, Robert M.

doi:10.1021/ja063651p

Cited by 66 publications

(47 citation statements)

References 32 publications

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“…The boronic acids, which recognize cis-diol configuration in saccharides and form reversible covalent complexes in aqueous media, represent an ideal synthetic molecular receptor having the ability to selectively recognize saccharides [14][15][16]. Phenylboronic acid derivatives have been developed for saccharide sensing in various methods based on piezoresistive microcantilevers [17], UV-vis absorption [18][19][20][21][22][23][24], fluorescence [22,[25][26][27][28][29][30], electrochemistry [31][32][33][34], plasmonics [35][36][37], holography [38][39][40]. Consequently, boronic acids can be used as the recognition moiety for detecting saccharides in solution.…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic analysis of the interaction between 3-aminophenylboronic acid and monosaccharides for development of biosensor

Torun

Dudak

Baş

et al. 2009

Sensors and Actuators B: Chemical

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Section: Introductionmentioning

confidence: 99%

Thermodynamic analysis of the interaction between 3-aminophenylboronic acid and monosaccharides for development of biosensor

Torun

Dudak

Baş

et al. 2009

Sensors and Actuators B: Chemical

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“…21 This is also the case for other simple and more complex compounds such as boronic acid-functionalized rhodamine derivatives. 19,22 Affinities to sugars can also be refined combining two different boronic acids. 22 Varying affinities were also observed in cases where boronic acids inhibit hydrolytic enzymes such as fatty acid amide hydrolase 23 (FAAH).…”

mentioning

confidence: 99%

“…19,22 Affinities to sugars can also be refined combining two different boronic acids. 22 Varying affinities were also observed in cases where boronic acids inhibit hydrolytic enzymes such as fatty acid amide hydrolase 23 (FAAH). Therefore, specificity could also result from a restricted affinity to a single protein.…”

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confidence: 99%

Boronic acids as tools to study (plant) developmental processes?

Matthes

Torres-Ruiz

2017

Plant Signaling & Behavior

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Boron (B) is an essential micronutrient for organisms. In plants, B is known to stabilize the cell wall by crosslinking Rhamnogalacturonan II through ester bonds formed with cis-diols of sugar moieties. However, B is believed to be required for additional functions such as stability and function of (plasma membrane) proteins involved in signal transduction pathways. We have recently shown that boronic acids, competitors of B, efficiently induce perfect phenocopies of monopteros mutants. This effect is enigmatic because like B, boronic acids should find numerous cellular targets and thus disturb many biologic processes ending in a spectrum of unspecific embryo phenotypes. Based on chemical characteristics of boronic acids and their derivatives we discuss reasons that could explain this unusual specificity. The peculiarities of this class of compounds could provide new tools for studying developmental processes. In fact B's capability to form (ester) cross-links between neighbored molecules through their cis-diol moieties is key for understanding its molecular functions. KEYWORDS 4,5Although boric acid is capable to enter and exit cells by diffusion, plasma membrane (PM) B transporters are required to adjust Bs homeostasis in plants when its concentration is too high or too low in the soil.6 Notably, active B transport is also necessary in mammals as shown by the electrogenic Na C -coupled B transporter NaBC1.7 Consequently, Bs significance for human and animal nutrition is discussed 8 and various observations in animals 9-11 support stabilizing roles for B in PM protein function -one possible target moiety being cis-diols of glycosyl residues. Interestingly, comparable roles for B in plant PM protein stability and in phytohormone signaling, specifically auxin (D IAA, indole-3-acetic acid), have been proposed. 12Our work places one possible role of B very near to these ideas. 13 It was prompted by an earlier report, where phenylboronic acid (PBA) was shown to induce monocotyly in Eranthis hyemalis.14 Boronic acids such as PBA are specific B competitors with the same binding specificity as boric acid but cannot serve to cross-link two molecules.15 PBA treatment of Arabidopsis thaliana embryos phenocopied monopteros mutants (mp-phenocopies) by specifically affecting embryonic root development. This process depends on two essential signals -the presence of an auxin maximum and of the transcription factor (TF) TARGET OF MONOPTEROS 7 (TMO7) in the hypophysis cell.16 Both signals are in-/ directly controlled by the TF MONOPTEROS (MP), which becomes active when its repressor BODENLOS (BDL) is degraded. This in turn depends -on the presence of auxin, which is mainly transported by the efflux carrier PIN-FORMED1 (PIN1). With this element a feedback loop regulation is established because MP itself activates PIN1 and TMO7. Our analysis of mp-phenocopies detected two possible points where PBA affects this system: the degradation of BDL and/or the stability of PIN1 at the PM.The induction of the mp phenocopies by boron...

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“…A biological example of conformational change induced by a compound containing a vicinal diol can be found in the purinergic receptor family of membrane-bound signalling proteins, which are activated primarily by the purine nucleoside adenosine 47,48 . Because the 2 ′ and 3 ′ hydroxyl groups of ribonucleosides can form stable cyclic boronates [49][50][51][52] , we explored the possibility that ribonucleosides might also be competent ligands for our own receptor mimic. Mixing receptor 4 with 2.0 equiv.…”

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confidence: 99%

End-to-end conformational communication through a synthetic purinergic receptor by ligand-induced helicity switching

et al. 2013

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The long-range communication of information, exemplified by signal transduction through membrane-bound receptors, is a central biochemical function. Reversible binding of a messenger ligand induces a local conformational change that is relayed through the receptor, inducing a chemical effect typically several nanometres from the binding site. We report a synthetic receptor mimic that transmits structural information from a boron-based ligand binding site to a spectroscopic reporter located more than 2 nm away. Reversible binding of a diol ligand to the N-terminal binding site induces a screw-sense preference in a helical oligo(aminoisobutyric acid) foldamer, which is relayed to a reporter group at the remote C-terminus, communicating information about the structure and stereochemistry of the ligand. The reversible nature of boronate esterification was exploited to switch the receptor sequentially between left- and right-handed helices, while the exquisite conformational sensitivity of the helical relay allowed the reporter to differentiate even between purine and pyrimidine nucleosides as ligands.

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Stereochemical and Regiochemical Trends in the Selective Detection of Saccharides

Cited by 66 publications

References 32 publications

Thermodynamic analysis of the interaction between 3-aminophenylboronic acid and monosaccharides for development of biosensor

Thermodynamic analysis of the interaction between 3-aminophenylboronic acid and monosaccharides for development of biosensor

Boronic acids as tools to study (plant) developmental processes?

End-to-end conformational communication through a synthetic purinergic receptor by ligand-induced helicity switching

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