Preparation and Sugar Binding Property of Microspheres Having Surface-anchored Phenylboronic Acid Groups

Abstract

Microspheres having phenylboronic acid groups on the resin surface were successfully prepared by emulsion polymerization of styrene, butyl acrylate, and m-acrylamidophenylboronic acid. The microspheres were swollen in an alkaline aqueous suspension by adding methylethylketone so that phenylboronic acid groups in the resin migrate out to the aqueous-organic interface in their ionized forms. d-Glucose was bound onto the microsphere by complex (ester) formation between phenylboronic acid moiety and cis-diol group of d-Glucose.

Chemoselective Removal of Dimeric 1,3-Diol Impurities Generated from Methyl Grignard Addition onto Esters

“…Cyclic boronates have been used as directing and protecting groups during synthesis, to affect separation of cis from trans diols, and as molecular sensors . Although five-membered cyclic boronates may be formed from cis and trans vicinal diols, angle strain frequently leads to easy hydrolysis …”

In situ product removal of ketoses by immobilized 3‐amino phenyl boronic acid: Effect of immobilization method on pH profile

“…The affinity of phenylboronic acids in aqueous solutions to diols is pH dependent, mostly binding at pH values higher than 8.5 and releasing the diol at lower pH (Sienkiewiczi and Roberts, 1980;Tsukagoshi et al, 1994). This pH profile may become a major problem in adaptation of the experience accumulating from affinity chromatography to ISPR needs, as many biotransformations are carried out at pH values lower than 8.5.…”

“…Commercially available immobilized phenyl boronic acids and most reported research work employing it or its derivatives are based on coupling of 3-amino phenyl boronic acid to the support via a stable amide bond, reported to affectively bind diols at pH values higher than pH 8.5 (Alvarez-Gonzalez et al, 1983;Chauhan et al, 1997;Singhal et al, 1991;Tsukagoshi et al, 1994). In this communication we report the results of a feasibility study on the effect of shifting from the previously employed amide bond coupling chemistry to N-alkyl coupling chemistrycoupling of 3-amino phenylboronic acid onto epoxide groups-on its pH profile of diol binding and its potential application for ISPR of a ketose product from aldosecontaining medium.…”