Skip to main content

Oligosaccharide Antigen Conjugation to Carrier Proteins to Formulate Glycoconjugate Vaccines

  • Protocol
  • First Online:
Vaccine Delivery Technology

Part of the book series: Methods in Molecular Biology ((MIMB,volume 2183))

Abstract

Conjugation, that is, covalent linkage, to immunological proteins is a common strategy to address the low immunogenicity issue of carbohydrate antigens in vaccine development. This chapter describes an easy and efficient method for oligosaccharide–protein conjugation employing dicarboxylic acid linkers. In this regard, a free amino group is introduced to an oligosaccharide antigen to facilitate coupling with the bifunctional linker upon reaction with its corresponding disuccinimidyl ester. The resultant monosuccinimidyl ester of the oligosaccharide antigen then reacts with the free amino groups of a carrier protein to provide the desired oligosaccharide–protein conjugate.

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

Access this chapter

Protocol
USD 49.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 109.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 139.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
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

Institutional subscriptions

References

  1. Monzavi-Karbassi B, Pashov A, Kieber-Emmons T (2013) Tumor-associated glycans and immune surveillance. Vaccine 1:174–203

    Article  CAS  Google Scholar 

  2. Hakomori SI (2001) Tumor-associated carbohydrate antigens defining tumor malignancy: basis for development of anti-cancer vaccines. Adv Exp Med Biol 491:369–402

    Article  CAS  Google Scholar 

  3. Danishefsky S, Allen J (2000) From the laboratory to the clinic: a retrospective on fully synthetic carbohydrate-based anticancer vaccines. Angew Chem Int Ed Engl 39:836–863

    Article  CAS  Google Scholar 

  4. Feng D, Shaikh AS, Wang F (2016) Recent advance in tumor-associated carbohydrate antigens (TACAs)-based antitumor vaccines. ACS Chem Biol 11:850–863

    Article  CAS  Google Scholar 

  5. Guo Z, Wang Q (2009) Recent development in carbohydrate-based cancer vaccines. Curr Opin Chem Biol 13:608–617

    Article  CAS  Google Scholar 

  6. Moyle PM, Toth I (2008) Self-adjuvanting lipopeptide vaccines. Curr Med Chem 15:506–516

    Article  CAS  Google Scholar 

  7. Hermanson GT (2013) The reactions of bioconjugation. In: Audet J, Preap M (eds) Bioconjugate techniques. Elsevier, Rockford, pp 229–258

    Chapter  Google Scholar 

  8. Gamblin DP, Scanlan EM, Davis BG (2009) Glycoprotein synthesis: an update. Chem Rev 109:131–163

    Article  CAS  Google Scholar 

  9. Jacques S, Rich JR, Ling C et al (2006) Chemoenzymatic synthesis of GM 3 and GM 2 gangliosides containing a truncated ceramide functionalized for glycoconjugate synthesis and solid phase applications. Org Biomol Chem 3:142–154

    Article  Google Scholar 

  10. Andersen SM, Ling C-C, Zhang P et al (2004) Synthesis of ganglioside epitopes for oligosaccharide specific immunoadsorption therapy of Guillian-Barré syndrome. Org Biomol Chem 2:1199–1212

    Article  CAS  Google Scholar 

  11. Wang Q, Xue J, Guo Z (2009) Synthesis of a monophosphoryl lipid A derivative and its conjugation to a modified form of a tumor-associated carbohydrate antigen GM3. Chem Commun 5536–5537

    Google Scholar 

  12. Liao G, Zhou Z, Suryawanshi S et al (2016) Fully synthetic self-adjuvanting α-2,9-oligosialic acid based conjugate vaccines against group C meningitis. ACS Cent Sci 2:210–218

    Article  CAS  Google Scholar 

  13. Toyokuni T, Dean B, Cai S et al (1994) Synthetic vaccines: synthesis of a dimeric Tn antigen-lipopeptide conjugate that elicits immune responses against Tn-expressing glycoproteins. J Am Chem Soc 116:395–396

    Article  CAS  Google Scholar 

  14. Wang Q, Ekanayaka SA, Wu J et al (2008) Synthetic and immunological studies of 5′-N-phenylacetyl sTN to develop carbohydrate-based cancer vaccines and to explore the impacts of linkage between carbohydrate antigens and carrier proteins. Bioconjug Chem 19:2060–2067

    Article  CAS  Google Scholar 

  15. Zhou Z, Liao G, Mandal SS et al (2015) A fully synthetic self-adjuvanting globo H-based vaccine elicited strong T cell-mediated antitumor immunity. Chem Sci 6:7112–7121

    Article  CAS  Google Scholar 

  16. Liao G, Zhou Z, Burgula S et al (2015) Synthesis and immunological studies of linear oligosaccharides of β-glucan as antigens for antifungal vaccine development. Bioconjug Chem 26:466–476

    Article  CAS  Google Scholar 

  17. Buskas T, Li Y, Boons G (2004) The immunogenicity of the tumor-associated antigen Lewis(y) may be suppressed by a bifunctional cross-linker required for coupling to a carrier protein. Chem Eur J 10:3517–3524

    Article  CAS  Google Scholar 

  18. Burgula S, Swarts BM, Guo Z (2012) Total synthesis of a glycosylphosphatidylinositol anchor of the human lymphocyte CD52 antigen. Chem Eur J 18:1194–1201

    Article  CAS  Google Scholar 

  19. Liao G, Zhou Z, Guo Z (2015) Synthesis and immunological study of α-2,9-oligosialic acid conjugates as anti-group C meningitis vaccines. Chem Commun 51:9647–9650

    Article  CAS  Google Scholar 

  20. Fournier E (2001) Colorimetric quantification of carbohydrates. In: Wrolstad RE, Acree TE, Decker EA et al (eds) Handbook of food analytical chemistry. Wiley, New York, pp E1.1.1–E1.1.8

    Google Scholar 

  21. Wu J, Guo Z (2006) Improving the antigenicity of sTn antigen by modification of its sialic acid residue for development of glycoconjugate cancer vaccines. Bioconjug Chem 17:1537–1544

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Zhongwu Guo .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2021 Springer Science+Business Media, LLC, part of Springer Nature

About this protocol

Check for updates. Verify currency and authenticity via CrossMark

Cite this protocol

Smith, B.R., Guo, Z. (2021). Oligosaccharide Antigen Conjugation to Carrier Proteins to Formulate Glycoconjugate Vaccines. In: Pfeifer, B.A., Hill, A. (eds) Vaccine Delivery Technology. Methods in Molecular Biology, vol 2183. Humana, New York, NY. https://doi.org/10.1007/978-1-0716-0795-4_15

Download citation

  • DOI: https://doi.org/10.1007/978-1-0716-0795-4_15

  • Published:

  • Publisher Name: Humana, New York, NY

  • Print ISBN: 978-1-0716-0794-7

  • Online ISBN: 978-1-0716-0795-4

  • eBook Packages: Springer Protocols

Publish with us

Policies and ethics