Synthesis of boronate‐functionalized organic‐inorganic hybrid monolithic column for the separation of cis‐diol containing compounds at low pH

Abstract

In this work, an organic-inorganic hybrid boronate affinity monolithic column was prepared via "one-pot" process using 4-vinylphenylboronic acid as organic monomer and divinylbenzene as cross-linker. The effects of reaction temperature, solvents and composition of organic monomers on the column properties (e.g. morphology, permeability, and mechanical stability) were investigated. A series of test compounds including small neutral molecules, aromatic amines, and cis-diol compounds were used to evaluate the retention behaviors of the prepared hybrid monolithic column. The results demonstrated that the prepared hybrid monolith exhibited mixed-interactions including hydrophilicity, cation exchange, and boronate affinity interaction. The run-to-run, day-to-day and batch-to-batch reproducibilities of the prepared hybrid monolith for thiourea's retention time were satisfactory with the relative standard deviations (RSDs) less than 0.09, 1.45 and 4.05% (n = 3), respectively, indicating the effectiveness and practicability of the proposed method.

Boronic acid‐functionalized agarose affinity chromatography for isolation of tropomyosin in fishes

“…In most cases the reversible covalent reaction efficiency between boronate affinity ligands and cis ‐diol‐containing compounds depends on the binding pH . In general, boronate affinity requires a solution pH higher than the pKa of boronic acid .…”

“…In most cases the reversible covalent reaction efficiency between boronate affinity ligands and cis-diol-containing compounds depends on the binding pH. 31 In general, boronate affinity requires a solution pH higher than the pKa of boronic acid. 32 Here, with different phosphate buffered saline buffers at pH levels ranging from 6.5 to 9.0, the purity of tropomyosin in the eluted fractions ( Fig.…”

Chromatographic separation of peptides and proteins for characterization of proteomes

“…free radical copolymerization, thiol-ene click chemistry). [81][82][83][84] Via the added orthogonal reactions with available monomers or organic groups, various kinds of functionalized hybrid monoliths could be designed, but these additional reactions might lead to the uncontrolled pore structure. The third approach is the copolymerization of organic monomers with polyhedral oligomeric silsesquioxane (POSS).…”

Preparation of an O-[2-(methacryloyloxy)-ethylcarbamoyl]-10,11-dihydroquinidine-silica hybrid monolithic column for the enantioseparation of amino acids by nano-liquid chromatography

“…Over the years, organic-inorganic hybrid monolithic columns have been developed because of their excellent permeability, higher pH stability, high surface, and superior performance [17][18][19]. Compared with the polymer-based and silica-based monoliths, the less shrinkage for organic-silica hybrid monolith has received increasing attention [20][21][22]. Hence, Tran et al [7,8] developed quinine-silica/zirconia and tertbutylcarbamoylquinine (tBuCQUI)-silica hybrid monolith using polyethylene glycol (PEG), vinyltrimethoxysilane (VTMS) and tetramethoxysilane (TMOS), which influence the phase separation time, hydrolyzation and condensation, respectively.…”