Preparation and characterization of fluorophenylboronic acid-functionalized monolithic columns for high affinity capture of cis-diol containing compounds

•Three fluorophenylboronic acid-functionalized monoliths were prepared.•The monoliths exhibited untrahigh boronate affinity toward cis-diol compounds.•The boronate affinity was strongly influenced by spacer arm length.•The monolith with appropriate spacer arm length can bind with cis-diols at pH 6.0...

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Vydáno v:	Journal of Chromatography A Ročník 1305; s. 123 - 130
Hlavní autoři:	Li, Qianjin, Lü, Chenchen, Liu, Zhen
Médium:	Journal Article
Jazyk:	angličtina
Vydáno:	Amsterdam Elsevier B.V 30.08.2013 Elsevier
Témata:	acids Affinity Analytical chemistry Binding binding capacity Biological and medical sciences Boronate affinity Boronic Acids - chemistry Capture Chemistry Chromatographic methods and physical methods associated with chromatography chromatography Chromatography, Affinity - instrumentation Cis-diol Enrichment Exact sciences and technology Fluorine - chemistry Fluorophenylboronic acid Glycoprotein glycoproteins humans Hydrogen-Ion Concentration Investigative techniques, diagnostic techniques (general aspects) Ligands Medical sciences Microscopy, Electron, Scanning Miscellaneous. Technology molecular weight Monolithic columns monosaccharides Nucleosides Other chromatographic methods Pathology. Cytology. Biochemistry. Spectrometry. Miscellaneous investigative techniques Spacers Urine Cis-diol Fluorophenylboronic acid Boronate affinity Monolithic columns Capture Biological fluid Chemical analysis Chromatographic retention Micellar electrokinetic capillary chromatography Esterases Pyrocatechol Diphenols Chemical enrichment Surface structure Affinity adsorbent Characterization Clinical biology Nucleoside Trace analysis Human Urine Scanning electron microscopy Diol Healthy subject Enzyme Monolithic column Morphology Preparation Hydrolases Boron Organic compounds Pancreatic ribonuclease Boronic acids
ISSN:	0021-9673, 1873-3778, 1873-3778
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Shrnutí:	•Three fluorophenylboronic acid-functionalized monoliths were prepared.•The monoliths exhibited untrahigh boronate affinity toward cis-diol compounds.•The boronate affinity was strongly influenced by spacer arm length.•The monolith with appropriate spacer arm length can bind with cis-diols at pH 6.0. Boronic acids are important ligands for the selective recognition and capture of cis-diol containing compounds, such as nucleosides and glycoproteins. In a recent study, it was found that 2,4-difluoro-3-formyl-phenylboronic acid (DFFPBA) exhibited an ultrahigh boronate affinity for binding with monosaccharides. Herein three DFFPBA-functionalized monolithic columns with varying spacer arms were synthesized and characterized. Different cis-diol containing compounds were used for the evaluation of the boronate affinity of the DFFPBA-functionalized monoliths. The DFFPBA-functionalized monoliths exhibited advantageous characteristics. These monoliths exhibited an ultrahigh boronate affinity toward cis-diol containing compounds. Moreover, the monolith with appropriate spacer arm exhibited a low binding pH (6.0) for cis-diols of small molecular weight. These advantages made DFFPBA-functionalized monoliths suitable for the enrichment of trace cis-diol containing compounds in neutral and weak acidic real samples. In addition, it was interesting that the length of spacer arms strongly influenced the boronate affinity: increasing the spacer arm resulted in apparently reduced boronate affinity, and inappropriate spacer arm length even eliminated the boronate affinity toward glycoprotein. To explain such a phenomenon, a possible mechanism was proposed. Finally, the potential of DFFPBA-functionalized monoliths for real applications was demonstrated with the selective enrichment of modified nucleosides from human urine.
Bibliografie:	http://dx.doi.org/10.1016/j.chroma.2013.07.007 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0021-9673 1873-3778 1873-3778
DOI:	10.1016/j.chroma.2013.07.007