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Preparation of a boronate-functionalized affinity hybrid monolith for specific capture of glycoproteins

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Abstract

A novel strategy for preparation of a boronate affinity hybrid monolith was developed using a Cu(I)-catalyzed 1,3-dipolar azide–alkyne cycloaddition (CuAAC) reaction of an alkyne–boronate ligand with an azide-functionalized monolithic intermediate. An azide-functionalized hybrid monolith was first synthesized via a single-step procedure to provide reactive sites for click chemistry; then the alkyne–boronate ligands were covalently immobilized on the azide-functionalized hybrid monolith via an in-column CuAAC reaction to form a boronate affinity hybrid monolith under mild conditions. The boronate affinity monolith was characterized and evaluated by means of elemental analysis, Fourier transform infrared spectroscopy, and scanning electron microscopy. The boronate affinity hybrid monolith exhibited excellent specificity toward nucleosides and glycoproteins, which were chosen as test cis-diol-containing compounds under neutral conditions. The binding capacity of the monolith for the glycoprotein ovalbumin was 2.36 mg · g-1 at pH 7.0. The practicability of the boronate affinity hybrid monolithic material was demonstrated by specific capture of the glycoproteins ovalbumin and ovotransferrin from an egg sample.

A novel strategy for preparation of boronate affinity hybrid monolith was developed by utilizing Cu(I)-catalyzed 1,3-dipolar azide-alkyne cycloaddition reaction (CuAAC). The obtained boronate affinity hybrid monolith exhibited excellent performance for isolation and enrichment of nucleosides and glycoproteins and was successfully employed to specific capture of glycoproteins from the egg sample

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Acknowledgments

The authors are grateful to the National Basic Research Program of China (no. 2012CB910601), the National Natural Science Foundation of China (no. 20935001, 21275080), the Research Fund for the Doctoral Program of Higher Education of China (no. 20120031110007), and the Natural Science Foundation of Tianjin (no. 10JCZDJC17600).

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Authors and Affiliations

  1. State Key Laboratory of Medical Chemical Biology, Department of Chemistry, Nankai University, Tianjin, 300071, China

    F. Yang, J. Mao, X. W. He, L. X. Chen & Y. K. Zhang

  2. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116011, China

    Y. K. Zhang

Authors
  1. F. Yang
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  2. J. Mao
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  3. X. W. He
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  4. L. X. Chen
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  5. Y. K. Zhang
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Correspondence to L. X. Chen or Y. K. Zhang.

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Yang, F., Mao, J., He, X.W. et al. Preparation of a boronate-functionalized affinity hybrid monolith for specific capture of glycoproteins. Anal Bioanal Chem 405, 5321–5331 (2013). https://doi.org/10.1007/s00216-013-6917-y

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  • DOI: https://doi.org/10.1007/s00216-013-6917-y

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