Advertisement

Microchimica Acta

, 185:308 | Cite as

Amorphous titania modified with boric acid for selective capture of glycoproteins

Original Paper
  • 122 Downloads

Abstract

Amorphous titania was modified with boric acid, and the resulting material was characterized by scanning electron microscopy, Fourier transform infrared spectroscopy, X-ray powder diffraction and X-ray photoelectron spectrometry. The new material, in contrast to conventional boronate affinity materials containing boronic acid ligands, bears boric acid groups. It is shown to exhibit high specificity for glycoproteins, and this was applied to design a method for solid phase extraction of glycoproteins as shown for ribonuclease B, horse radish peroxidase and ovalbumin. Glycoproteins were captured under slightly alkaline environment and released in acidic solutions. The glycoproteins extracted were detected by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. The binding capacities for ribonuclease B, horse radish peroxidase and ovalbumin typically are 9.3, 26.0 and 53.0 mg ∙ g−1, respectively. The method was successfully applied to the selective enrichment of ovalbumin from egg white.

Graphical abstract

Schematic presentation of the capture of glycoproteins by amorphous titania modified with boric acid.

Keywords

Boronate affinity Solid phase extration Ovalbumin Horse radish peroxidase Ribonuclease B 

Notes

Funding

This work has been supported by the Natural Science Foundation of Hubei Province of China (no. 2014CFB179).

Compliance with ethical standards

The authors declare that they have no competing interests.

Supplementary material

604_2018_2824_MOESM1_ESM.doc (796 kb)
ESM 1 (DOC 796 kb)

References

  1. 1.
    Furukawa K, Kobata A (1992) Protein glycosylation. Curr Opin Biotechnol 3:554–559CrossRefGoogle Scholar
  2. 2.
    Rudd PM, Elliott T, Cresswell P, Wilson IA, Dwek RA (2001) Glycosylation and the immune system. Science 291:2370–2376CrossRefGoogle Scholar
  3. 3.
    Gabius HJ (2011) Glycobiomarkers by glycoproteomics and glycan profiling (glycomics): emergence of functionality. Biochem Soc Trans 39:399–405CrossRefGoogle Scholar
  4. 4.
    Zielinska DF, Gnad F, Wisnewski JR, Mann M (2010) Precision mapping of an in vivo N-glycoproteome reveals rigid topological and sequence constraints. Cell 141:897−907CrossRefGoogle Scholar
  5. 5.
    Monzo A, Bonn GK, Guttman A (2007) Lectin-immobilization strategies for affinity purification and separation of glycoconjugates. TrAC Trends Anal Chem 26:423−432CrossRefGoogle Scholar
  6. 6.
    Zhang H, Li XJ, Martin DB, Aebersold R (2003) Identification and quantification of N-linked glycoproteins using hydrazide chemistry, stable isotope labeling and mass spectrometry. Nat Biotechnol 21:660−666Google Scholar
  7. 7.
    Zhang Y, Zhuang Y, Shen H, Chen X, Wang J (2017) A super hydrophilic silsesquioxane-based composite for highly selective adsorption of glycoproteins. Microchim Acta 184:1037–1044CrossRefGoogle Scholar
  8. 8.
    Guan F, Uboh CE, Soma LR, Birks E, Chen J, Mitchell J, You Y, Rudy J, Xu F, Li X, Mbuy G (2007) LC-MS/MS method for confirmation of recombinant human erythropoietin and darbepoetin alpha in equine plasma. Anal Chem 79:4627–4635CrossRefGoogle Scholar
  9. 9.
    Li D, Chen Y, Liu Z (2015) Boronate affinity materials for separation and molecular recognition: structure, properties and applications. Chem Soc Rev 44:8097–8123CrossRefGoogle Scholar
  10. 10.
    Li X, Pennington J, Stobaugh JF, Schoeich C (2008) Synthesis of sulfonamide- and sulfonyl-phenylboronic acid-modified silica phases for boronate affinity chromatography at physiological pH. Anal Biochem 372:227–236CrossRefGoogle Scholar
  11. 11.
    Wulff G (1982) Selective binding to polymers via covalent bonds. The construction of chiral cavities as specific receptor sites. Pure Appl Chem 54:2093–2102CrossRefGoogle Scholar
  12. 12.
    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 128:4226–4227CrossRefGoogle Scholar
  13. 13.
    Lü C, Li H, Wang H, Liu Z (2013) Probing the interactions between boronic acids and cis-diol-containing biomolecules by affinity capillary electrophoresis. Anal Chem 85:2361–2369CrossRefGoogle Scholar
  14. 14.
    Ren L, Liu Z, Liu Y, 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 48:6704–6707CrossRefGoogle Scholar
  15. 15.
    Espina-Benitez MB, Randon J, Demesmay C, Dugas V (2017) Back to BAC: insights into boronate affinity chromatography interaction mechanisms. Sep Purif Rev 00:1–15Google Scholar
  16. 16.
    Yang Q, Huang D, Zhou P (2014) Synthesis of a SiO2/TiO2 hybrid boronate affinity monolithic column for specific capture of glycoproteins under neutral conditions. Analyst 139:987–991CrossRefGoogle Scholar
  17. 17.
    Yang Q, Huang D, Jin S, Zhou H, Zhou P (2013) One-step synthesis of an organic–inorganic hybrid boronate affinity monolithic column with synergistic co-monomers. Analyst 138:4752–4755CrossRefGoogle Scholar
  18. 18.
    Wang ST, Chen D, Ding J, Yuan BF, Feng YQ (2013) Borated titania, a new option for the selective enrichment of cis-diol biomolecules. Chem Eur J 19:606–612CrossRefGoogle Scholar
  19. 19.
    Li J, Xia S, Gao S (1995) FT-IR and Raman spectroscopic study of hydrated borates. Spectrochim Acta 51A:519–532Google Scholar
  20. 20.
    Feng N, Zheng A, Wang Q, Ren P, Gao X, Liu S, Shen Z, Chen T, Deng F (2011) Boron environments in B-doped and (B, N)-codoped TiO2 photocatalysts: a combined solid-state NMR and theoretical calculation study. J Phys Chem C 115:2709–2719CrossRefGoogle Scholar
  21. 21.
    Zhao W, Ma W, Chen C, Zhao J, Shuai Z (2004) Efficient degradation of toxic organic pollutants with Ni2O3/TiO2-xBx under visible irradiation. J Am Chem Soc 126:4782–4783CrossRefGoogle Scholar
  22. 22.
    Feng N, Wang Q, Zheng A, Zhang Z, Fan J, Liu SB, Amoureux JP, Deng F (2013) Understanding the high photocatalytic activity of (B, Ag)-codoped TiO2 under solar-light irradiation with XPS, solid-state NMR, and DFT calculations. J Am Chem Soc 135:1607–1616CrossRefGoogle Scholar
  23. 23.
    Liu G, Zhao Y, Sun C, Li F, Lu GQ, Cheng H (2008) Synergistic effects of B/N doping on the visible-light photocatalytic activity of mesoporous TiO2. Angew Chem Int Ed 47:4516–4520CrossRefGoogle Scholar
  24. 24.
    Li L, Yang Y, Liu X, Fan R, Shi Y, Li S, Zhang L, Fan X, Tang P, Xu R, Zhang W, Wang Y, Ma L (2013) A direct synthesis of B-doped TiO2 and its photocatalytic performance on degradation of RhB. Appl Surf Sci 265:36–40CrossRefGoogle Scholar
  25. 25.
    Dong L, Feng S, Li S, Song P, Wang J (2015) Preparation of concanavalin A-chelating magnetic nanoparticles for selective enrichment of glycoproteins. Anal Chem 87:6849–6853CrossRefGoogle Scholar
  26. 26.
    Bie Z, Chen Y, Ye J, Wang S, Liu Z (2015) Boronate-affinity glycan-oriented surface imprinting: a new strategy to mimic lectins for the recognition of an intact glycoprotein and its characteristic fragments. Angew Chem Int Ed 54:10211–10215CrossRefGoogle Scholar
  27. 27.
    Sun X, Ma R, Chen J, Shi Y (2017) Boronate-affinity based magnetic molecularly imprinted nanoparticles for the efficient extraction of the model glycoprotein horseradish peroxidase. Microchim Acta 184:3729–3737CrossRefGoogle Scholar
  28. 28.
    Jiang L, Messing ME, Ye L (2017) Temperature and pH dual-responsive core-brush nanocomposite for enrichment of glycoproteins. ACS Appl Mater Interfaces 9:8985–8995CrossRefGoogle Scholar
  29. 29.
    Zhou C, Chen X, Du Z, Li G, Xiao X, Cai Z (2017) A hybrid monolithic column based on boronate-functionalized graphene oxide nanosheets for online specific enrichment of glycoproteins. J Chromatogr A 1498:90–98CrossRefGoogle Scholar
  30. 30.
    Yang J, He X, Chen L, Zhang Y (2017) Thiol-yne click synthesis of boronic acid functionalized silica nanoparticle-graphene oxide composites for highly selective enrichment of glycoproteins. J Chromatogr A 1513:118–125CrossRefGoogle Scholar
  31. 31.
    Wu Q, Jiang B, Weng Y, Liu J, Li S, Hu Y, Yang K, Liang Z, Zhang L, Zhang Y (2018) 3-Carboxybenzoboroxole functionalized polyethylenimine modified magnetic graphene oxide nanocomposites for human plasma glycoproteins enrichment under physiological condition. Anal Chem 90:2671–2677CrossRefGoogle Scholar
  32. 32.
    Li D, Bie Z (2017) Branched polyethyleneimine-assisted boronic acid-functionalized magnetic nanoparticles for the selective enrichment of trace glycoproteins. Analyst 142:4494–4502CrossRefGoogle Scholar
  33. 33.
    Su J, He X, Chen L, Zhang Y (2018) A combination of "thiol-ene" click chemistry and surface initiated atom transfer radical polymerization: fabrication of boronic acid functionalized magnetic graphene oxide composite for enrichment of glycoproteins. Talanta 180:54–60CrossRefGoogle Scholar
  34. 34.
    Zhang D, Chen Q, Hu L, Chen X, Wang J (2015) Preparation of a cobalt mono-substituted silicotungstic acid doped with aniline for the selective adsorption of ovalbumin. J Mater Chem B 3:4363–4369CrossRefGoogle Scholar
  35. 35.
    Apostol I, Miller KJ, Ratto J, Kelner DN (2009) Comparison of different approaches for evaluation of the detection and quantitation limits of a purity method: a case study using a capillary isoelectrofocusing method for a monoclonal antibody. Anal Biochem 385:101−106CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Key Laboratory of Analytical Chemistry for Biology and Medicine (Ministry of Education), College of Chemistry and Molecular SciencesWuhan UniversityWuhanPeople’s Republic of China

Personalised recommendations