Abstract
Boronate affinity monolithic columns have been developed into an important means for the selective recognition and capture of cis-diol-containing biomolecules, such as glycoproteins, nucleosides and saccharides. The ligands of boronic acids are playing an important role in boronate affinity monolithic columns. Although several boronate affinity monoliths with high affinity toward cis-diol-containing biomolecules have been reported, only few publications are focused on their detailed procedures for preparation and characterization. This chapter describes in detail the preparation and characterization of a boronate affinity monolithic column applying 2,4-difluoro-3-formyl-phenylboronic acid (DFFPBA) as a ligand. The DFFPBA-functionalized monolithic column not only exhibited an ultrahigh boronate affinity toward cis-diol-containing biomolecules, but also showed great potential for the selective enrichment of cis-diol-containing biomolecules in real samples.
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References
James TD, Sandanayake K, Shinkai S (1996) Saccharide sensing with molecular receptors based on boronic acid. Angew Chem Int Ed 35:1910–1922
Lee JH, Kim YS, Ha MY, Lee EK, Choo JB (2005) Immobilization of aminophenylboronic acid on magnetic beads for the direct determination of glycoproteins by matrix assisted laser desorption ionization mass spectrometry. J Am Soc Mass Spectrom 16:1456–1460
Xu Y, Wu Z, Zhang L, Lu HJ, Yang PY, Webley PA, Zhao DY (2009) Highly specific enrichment of glycopeptides using boronic acid-functionalized mesoporous silica. Anal Chem 81:503–508
Tang J, Liu YC, Qi DW, Yao GP, Deng CH, Zhang XM (2009) On-plate-selective enrichment of glycopeptides using boronic acid-modified gold nanoparticles for direct MALDI-QIT-TOF MS analysis. Proteomics 9:5046–5055
Zhang LJ, Xu YW, Yao HL, Xie LQ, Yao J, Lu HJ, Yang PY (2009) Boronic acid functionalized core-satellite composite nanoparticles for advanced enrichment of glycopeptides and glycoproteins. Chem Eur J 15:10158–10166
Ren LB, Liu YC, Dong MM, Liu Z (2009) Synthesis of hydrophilic baronage affinity monolithic capillary for specific capture of glycoproteins by capillary liquid chromatography. J Chromatogr A 1216:8421–8425
Ren LB, Liu Z, Dong MM, Ye ML, Zou HF (2009) Synthesis and characterization of a new boronate affinity monolithic capillary for specific capture of cis-diol-containing compounds. J Chromatogr A 1216:4768–4774
Jiang YQ, Ma YF (2009) A fast capillary electrophoresis method for separation and quantification of modified nucleosides in urinary samples. Anal Chem 81:6474–6480
Chen M, Lu Y, Ma Q, Guo L, Feng YQ (2009) Boronate affinity monolith for highly selective enrichment of glycopeptides and glycoproteins. Analyst 134:2158–2164
Lu Y, Bie ZJ, Liu YC, Liu Z (2013) Fine-tuning the specificity of boronate affinity monoliths toward glycoproteins through pH manipulation. Analyst 138:290–298
Lin ZA, Pang JL, Yang HH, Cai ZW, Zhang L, Chen GN (2011) One-pot synthesis of an organic-inorganic hybrid affinity monolithic column for specific capture of glycoproteins. Chem Commun 47:9675–9677
Lin ZA, Pang JL, Lin Y, Huang H, Cai ZW, Zhang L, Chen GN (2011) Preparation and evaluation of a phenylboronate affinity monolith for selective capture of glycoproteins by capillary liquid chromatography. Analyst 136:3281–3288
Hjerten S, Li YM, Liao JL, Mohammad J, Nakazato K, Pettersson G (1992) Continuous beds - high-resolving, cost-effective chromatographic matrices. Nature 356:810–811
Svec F, Frechet JMJ (1996) New designs of macroporous polymers and supports: from separation to biocatalysis. Science 273:205–211
Li HY, Liu Z (2012) Recent advances in monolithic column-based boronate-affinity chromatography. Trends Anal Chem 37:148–161
Li XB, Pennington J, Stobaugh JF, Schöneich C (2008) Synthesis of sulfonamide- and sulfonyl-phenylboronic acid-modified silica phases for boronate affinity chromatography at physiological pH. Anal Biochem 372:227–236
Matsumoto A, Yoshida R, Kataoka K (2004) Glucose-responsive polymer gel bearing phenylborate derivative as a glucose-sensing moiety operating at the physiological pH. Biomacromolecules 5:1038–1045
Matsumoto A, Yamamoto K, Yoshida R, Kataoka K, Aoyagi T, Miyahara Y (2010) A totally synthetic glucose responsive gel operating in physiological aqueous conditions. Chem Commun 46:2203–2205
Liu YC, Ren LB, Liu Z (2011) A unique boronic acid functionalized monolithic capillary for specific capture, separation and immobilization of cis-diol biomolecules. Chem Commun 47:5067–5069
Li QJ, Lü CC, Li HY, Liu YC, Wang HY, Wang X, Liu Z (2012) Preparation of organic-silica hybrid boronate affinity monolithic column for the specific capture and separation of cis-diol-containing compounds. J Chromatogr A 1256:114–120
Li QJ, Lü CC, Liu Z (2013) Preparation and characterization of fluorophenylboronic acid-functionalized monolithic columns for high affinity capture of cis-diol-containing compounds. J Chromatogr A 1305:123–130
Wulff G (1982) Selective binding to polymers via covalent bonds – the construction of chiral cavities as specific receptor-sites. Pure Appl Chem 54:2093–2102
Li HY, Liu YC, Liu J, Liu Z (2011) A Wulff-type boronate for boronate affinity capture of cis-diol compounds at medium acidic pH condition. Chem Commun 47:8169–8171
Berube M, Dowlut M, Hall DG (2008) Benzoboroxoles as efficient glycopyranoside-binding agents in physiological conditions: structure and selectivity of complex formation. J Org Chem 73:6471–6479
Dowlut M, Hall DG (2006) An improved class of sugar-binding boronic acids, soluble and capable of complexing glycosides in neutral water. J Am Chem Soc 128:4226–4227
Pal A, Berube M, Hall DG (2010) Design, synthesis, and screening of a library of peptidyl bis(boroxoles) as oligosaccharide receptors in water: identification of a receptor for the tumor marker TF-antigen disaccharide. Angew Chem Int Ed 49:1492–1495
Schumacher S, Katterle M, Hettrich C, Paulke BR, Hall DG, Scheller FW, Gajovic-Eichelmann N (2011) Label-free detection of enhanced saccharide binding at pH 7.4 to nanoparticulate benzoboroxole based receptor units. J Mol Recognit 24:953–959
Li HY, Wang HY, Liu YC, Liu Z (2012) A benzoboroxole-functionalized monolithic column for the selective enrichment and separation of cis-diol-containing biomolecules. Chem Commun 48:4115–4117
Ren LB, Liu Z, Liu YC, Dou P, Chen HY (2009) Ring-opening polymerization with synergistic co-monomers: access to a boronate-functionalized polymeric monolith for the specific capture of cis-diol-containing biomolecules under neutral conditions. Angew Chem Int Ed 48:6704–6707
Liang L, Liu Z (2011) A self-assembled molecular team of boronic acids at the gold surface for specific capture of cis-diol biomolecules at neutral pH. Chem Commun 47:2255–2257
Lü CC, Li HY, Wang HY, Liu Z (2013) Probing the interactions between boronic acids and cis-diol-containing biomolecules by affinity capillary electrophoresis. Anal Chem 85:2361–2369
Acknowledgement
We gratefully acknowledge the financial support from the National Natural Science Foundation of China (grants nos. 21075063, 21275073, and 21121091), the Natural Science Foundation of Jiangsu Province (grant no. KB2011054), and the Ministry of Science and Technology of China (grant no. 35-15).
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Li, Q., Liu, Z. (2015). Preparation and Characterization of Fluorophenylboronic Acid-Functionalized Affinity Monolithic Columns for the Selective Enrichment of cis-Diol-Containing Biomolecules. In: Reichelt, S. (eds) Affinity Chromatography. Methods in Molecular Biology, vol 1286. Humana Press, New York, NY. https://doi.org/10.1007/978-1-4939-2447-9_13
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DOI: https://doi.org/10.1007/978-1-4939-2447-9_13
Publisher Name: Humana Press, New York, NY
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