Molecular imprinting of fructose using a polymerizable benzoboroxole: Effective complexation at pH 7.4

Lewis acidity and sugar receptor activity of 3-amino-substituted benzoxaboroles and their ortho-aminomethylphenylboronic acid analogues

“…2). Quite surprisingly, the pK a s determined for the 3-amino-substituted benzoxaboroles (2a-c) are equal within the 15 experimental error and almost the same as the one for 1. Since the parent amines differ considerably in basicity, no difference in pK a s of 2a-c means that the amino substituent is not involved in the acid-base equilibrium.…”

“…The monocrystal of the compound 5a was obtained by slow evaporation of the solvents after removal of the drying agent. 15 Crystal structure of the obtained complex was determined by Xray diffraction technique. Similarly to Anslyn et al 42 findings, instead of phenylboronic catechol ester with three coordinated boron center (5), a methoxylated boronate (5a) was detected in the crystalline state.…”

“…The apparent binding constants of 1, the 3-amino-substituted benzoxaboroles (2a-c) and piperidinylmethylphenylboronic acid (3c) with glucose, galactose and fructose have been quantitatively evaluated using the Springsteen and Wang method. 36 The 15 determined K values have been compared with the previously reported binding constants of 3a and 3b. 45 As differences in solution composition may strongly influence the binding constants values, all the measurements have been carried out at the same conditions (methanol-0.1 M aqueous phosphate buffer 20 pH = 7.4 (1:1, v/v) + 1 vol% DMSO), close to the physiological ones.…”

Label‐free detection of enhanced saccharide binding at pH 7.4 to nanoparticulate benzoboroxole based receptor units

“…Functionalized phenylboronic acids bearing the possibility to intramolecularly coordinate to the boron, for example, an aminomethyl‐group in ortho position to the boron introduced by Wulff (; Bhat et al ., ), and more recently, 1‐hydroxymethyl‐phenylboronic acids (benzoboroxoles), introduced by Hall (Hall and Dowlut, ; Berube et al ., ), offer a remedy for the unfavorable pH effect. Especially the benzoboroxole holds great promise because of their significantly higher binding energy compared with arylboronic acids, including the Wulff‐type ortho‐aminoalkyl derivatives (Berube et al ., ; Schumacher et al ., ). In this regard, the benzoboroxole offers the possibility of binding to neutral saccharide in aqueous environments.…”

4-Nitrophenol surface molecularly imprinted polymers based on multiwalled carbon nanotubes for the elimination of paraoxon pollution

“…Molecular imprinting is a technique to make selective binding sites in the process of polymer synthesis through adding a certain molecule as the template. The formation of imprinting efficiency is mainly based on the interactions between template and imprinted polymers such as covalent interactions [6][7][8], non-covalent interactions [9][10][11][12], electrostatic interactions [13,14] and metal ion coordination [15,16]. In recent years molecularly imprinted polymers have received more and more attention because they are easy and cheap to synthesize and have strong stability to endure the destroying from the environment, so they are extensively applied in quite a lot of fields like analytical separations, enzyme-like catalysis, chemical sensors and drug delivery [17][18][19][20][21][22].…”