Skip to main content
SpringerLink
Log in
Book cover

Affinity Chromatography pp 297–307Cite as

Characterization of the Binding Strengths Between Boronic Acids and cis-Diol-Containing Biomolecules by Affinity Capillary Electrophoresis

  • Protocol

  • 3227 Accesses

Part of the book series: Methods in Molecular Biology ((MIMB,volume 1286))

Abstract

The affinity of boronic acids toward cis-diol-containing biomolecules has found wide applications in many fields, such as sensing, separation, drug delivery, and functional materials. A sound understanding of the binding interactions will greatly facilitate exquisite applications of this chemistry. Traditional techniques are associated with some apparent drawbacks, so they are only applicable to a limited range of boronic acids and cis-diol-containing biomolecules. This chapter describes an affinity capillary electrophoresis (ACE) method for the characterization of the binding strengths between boronic acids and cis-diol-containing biomolecules. As compared with existing approaches, such as 11B NMR, the ACE method exhibits several significant advantages: (1) possibility of simultaneous study of multiple interactions, (2) low requirement on the purity of the binding species, (3) widely applicable to almost all types of cis-diol-containing compounds and boronic acids, and (4) high accuracy and precision.

This is a preview of subscription content, log in via an institution.

Protocol
USD   49.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   119.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Springer Nature is developing a new tool to find and evaluate Protocols. Learn more

References

  1. Elstner M, Weisshart K, Müllen K, Schiller A (2012) Molecular logic with a saccharide probe on the few-molecules level. J Am Chem Soc 134:8098–8100

    Article  CAS  PubMed  Google Scholar 

  2. Liu Y, Deng C, Tang L, Qin AJ, Hu RR, Sun JZ, Tang BZ (2011) Specific detection of d-glucose by a tetraphenylethene-based fluorescent sensor. J Am Chem Soc 133:660–663

    Article  CAS  PubMed  Google Scholar 

  3. 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

    Article  CAS  Google Scholar 

  4. Liu Y, Lu Y, Liu Z (2012) Restricted access boronate affinity porous monolith as a protein A mimetic for the specific capture of immunoglobulin G. Chem Sci 3:1467–1471

    Article  CAS  Google Scholar 

  5. 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 48:6704–6707

    Article  CAS  Google Scholar 

  6. Ren L, Liu Y, Dong M, Liu Z (2009) Synthesis of hydrophilic boronate affinity monolithic capillary for specific capture of glycoproteins by capillary liquid chromatography. J Chromatogr A 1216:8421–8425

    Article  CAS  PubMed  Google Scholar 

  7. Li H, Liu Z (2012) Recent advances in monolithic column-based boronate-affinity chromatography. Trends Anal Chem 37:148–161

    Article  CAS  Google Scholar 

  8. 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

    Article  CAS  PubMed  Google Scholar 

  9. Nishiyabu R, Kubo Y, James TD, Fossey JS (2011) Boronic acid building blocks: tools for self assembly. Chem Commun 47:1124–1150

    Article  CAS  Google Scholar 

  10. 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

    Article  CAS  Google Scholar 

  11. Vlandas A, Kurkina T, Ahmad A, Kern K, Balasubramanian K (2010) Enzyme-free sugar sensing in microfluidic channels with an affinity-based single-wall carbon nanotube sensor. Anal Chem 82:6090–6097

    Article  CAS  PubMed  Google Scholar 

  12. Li Y, Xiao W, Xiao K, Berti L, Luo JT, Tseng HP, Fung G, Lam KS (2012) Well-defined, reversible boronate crosslinked nanocarriers for targeted drug delivery in response to acidic ph values and cis-diols. Angew Chem Int Ed 51:2864–2869

    Article  CAS  Google Scholar 

  13. Kim H, Kang YJ, Kang S, Kim KT (2012) Monosaccharide-responsive release of insulin from polymersomes of polyboroxole block copolymers at neutral pH. J Am Chem Soc 134:4030–4033

    Article  CAS  PubMed  Google Scholar 

  14. Ellis GA, Palte MJ, Raines RT (2012) Boronate-mediated biologic delivery. J Am Chem Soc 134:3631–3634

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  15. Chen W, Cheng Y, Wang B (2012) Dual-responsive boronate crosslinked micelles for targeted drug delivery. Angew Chem Int Ed 51:5293–5295

    Article  CAS  Google Scholar 

  16. Chapelle S, Verchere JF (1988) A 11B- and 13C-NMR determination of the structures of borate complexes of pentoses and related sugars. Tetrahedron 44:4469–4482

    Article  CAS  Google Scholar 

  17. Sinton SW (1987) Complexation chemistry of sodium-borate with poly(vinylalcohol) and small diols: a boron-11 NMR study. Macromolecules 20:2430–2441

    Article  CAS  Google Scholar 

  18. Vanduin M, Peters JA, Kieboom APG, Vanbekkum H (1984) Studies on borate esters 1: the pH-dependence of the stability of esters of boric-acid and borate in aqueous-medium as studied by 11B-NMR. Tetrahedron 40:2901–2911

    Article  CAS  Google Scholar 

  19. Henderson WG, How MJ, Kennedy GR, Mooney EF (1973) Interconversion of aqueous boron species and interaction of borate with diols: a 11B NMR study. Carbohydr Res 28:1–12

    Article  CAS  Google Scholar 

  20. Yan J, Springsteen G, Deeter S, Wang BH (2004) The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols – it is not as simple as it appears. Tetrahedron 60:11205–11209

    Article  CAS  Google Scholar 

  21. Springsteen G, Wang BH (2002) A detailed examination of boronic acid-diol complexation. Tetrahedron 58:5291–5300

    Article  CAS  Google Scholar 

  22. Springsteen G, Wang BH (2001) Alizarin Red S. as a general optical reporter for studying the binding of boronic acids with carbohydrates. Chem Commun 17:1608–1609

    Article  Google Scholar 

  23. De Guzman JM, Soper SA, McCarley RL (2010) Assessment of glycoprotein interactions with 4-(2-aminoethyl)carbamoyl phenylboronic acid surfaces using surface plasmon resonance spectroscopy. Anal Chem 82:8970–8977

    Article  PubMed  Google Scholar 

  24. Liu JT, Chen LY, Shih MC, Chang Y, Chen WY (2008) The investigation of recognition interaction between phenylboronate monolayer and glycated hemoglobin using surface plasmon resonance. Anal Biochem 375:90–96

    Article  CAS  PubMed  Google Scholar 

  25. Wiskur SL, Lavigne JL, Metzger A, Tobey SL, Lynch V, Anslyn EV (2004) Thermodynamic analysis of receptors based on guanidinium/boronic acid groups for the complexation of carboxylates, alpha-hydroxycarboxylates, and diols: driving force for binding and cooperativity. Chem Eur J 10:3792–3804

    Article  CAS  PubMed  Google Scholar 

  26. Nicholls MP, Paul PKC (2004) Structures of carbohydrate-boronic acid complexes determined by NMR and molecular modelling in aqueous alkaline media. Org Biomol Chem 2:1434–1441

    Article  CAS  PubMed  Google Scholar 

  27. Tsukagoshi K, Shinkai S (1991) Specific complexation with monosaccharides and disaccharides that can be detected by circular-dichroism. J Org Chem 56:4089–4091

    Article  CAS  Google Scholar 

  28. 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 85:2361–2369

    Article  PubMed  Google Scholar 

  29. Tanaka Y, Terabe S (2002) Estimation of binding constants by capillary electrophoresis. J Chromatogr B 768:81–92

    Article  CAS  Google Scholar 

  30. Li N, Zeng S, He L, Zhong WW (2010) Probing nanoparticle-protein interaction by capillary electrophoresis. Anal Chem 82:7460–7466

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Hankou Road 22, Nanjing, 210093, China

    Chenchen Lü & Zhen Liu

Authors
  1. Chenchen Lü
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zhen Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zhen Liu .

Editor information

Editors and Affiliations

  1. Leibniz-Institut für Oberflächenmodifizierung, Leipzig, Germany

    Senta Reichelt

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer Science+Business Media New York

About this protocol

Cite this protocol

Lü, C., Liu, Z. (2015). Characterization of the Binding Strengths Between Boronic Acids and cis-Diol-Containing Biomolecules by Affinity Capillary Electrophoresis. 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_23

Download citation

  • DOI: https://doi.org/10.1007/978-1-4939-2447-9_23

  • Publisher Name: Humana Press, New York, NY

  • Print ISBN: 978-1-4939-2446-2

  • Online ISBN: 978-1-4939-2447-9

  • eBook Packages: Springer Protocols

Publish with us

Policies and ethics

Search

Navigation