Skip to main content
SpringerLink
Log in

Synthesis of oligosaccharides with oligoethylene glycol spacers and their conversion into glycoconjugates usingN,N,N′,N″-tetramethyl(succinimido)uronium tetrafluoroborate as coupling reagent

  • Papers
  • Published:
Glycoconjugate Journal Aims and scope Submit manuscript

Abstract

Glycosides of glucose and lactose with di- and tetraethylene glycols, transformed into bifunctional (alcohol, ester) spacer molecules, have been synthesized. After deprotection, these spacer glycosides, containing a free carboxyl group, have been transformed efficiently into glycoconjugates usingN,N,N′,N″-tetramethyl(succinimido)uronium tetrafluoroborate (TSTU) for the formation of an active ester.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Feizi T (1981)Trends Biochem Sci 12:333–35.

    Google Scholar 

  2. Sharon N (1984)Trends Biochem Sci 15:198–202.

    Google Scholar 

  3. Garegg PJ, Lindberg AA (1988)Carbohydrate Chemistry (Kennedy JF, ed) pp. 500–59. Oxford: Clarendon Press.

    Google Scholar 

  4. Kallin E (1990) Thesis, University of Lund, Sweden.

    Google Scholar 

  5. Harris M (1985)Macr Mol Chem Phys C25:325–73.

    Google Scholar 

  6. Verez-Bencomo V, Campos-Valdes MT, Marino-Albernas JR, Fernandez-Santanam V, Hernandez-Renzoli M, Perez-Martinez CS (1991)Carbohydr Res 271:263–67.

    Google Scholar 

  7. Bertozzi CR, Bednarski MD (1991)J Org Chem 56:4326–29.

    Google Scholar 

  8. Inman JK, Merchant B, Clafin L, Tacey SE (1973)Immunochemistry 10:165–74.

    Google Scholar 

  9. Bannwarth W, Schmidt D, Stallard RL, Hornung C, Knorr R, Müller F (1988)Helv Chim Acta 71:2085–99.

    Google Scholar 

  10. Bannwarth B, Knorr R (1991)Tetrahedron Lett 32:1157–60.

    Google Scholar 

  11. Jullien L, Lehn JM (1988)Tetrahedron Lett 29:3803–6.

    Google Scholar 

  12. Magnusson G, Noori G, Dahmén J, Frejd T, Lave T (1981)Acta Chem Scand B 35:213–16.

    Google Scholar 

  13. Fügedi P, Garegg PJ (1986)Carbohydr Res 149:c9-c12.

    Google Scholar 

  14. Garegg PJ, Norberg T (1979)Acta Chem Scand B 33:116–18.

    Google Scholar 

  15. Timkovich R (1977)Biochem Biophys Res Commun 74:1463–68.

    Google Scholar 

  16. Hodge JE, Hofreiter BT (1962)Methods Carbohydr Chem I:388.

    Google Scholar 

  17. Peters, Jr T (1968)Chr Chem 14:1147.

    Google Scholar 

  18. Lundblad RL, Noyes CM (1984)Chemical Reagents for Protein Modification, Vol. 1, p. 127. Boca Raton: CRC Press.

    Google Scholar 

  19. Barrelle M, Béguin C, Tessier S (1982)Org Magn Reson 19:102–4.

    Google Scholar 

  20. Kimble BJ (1978)High Performance Mass Spectrometry: Chemical Applications (Gross ML, ed). Washington, DC: American Chemical Society.

    Google Scholar 

  21. Biemann K (1990)Methods Enzymol 193:295–305.

    Google Scholar 

  22. Gilliam JM, Landis PW, Occolowitz JL (1990)Anal Chem 56:2285–88.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91, Stockholm, Sweden

    Mats Andersson, Stefan Oscarson & Liselotte Öberg

Authors
  1. Mats Andersson
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Stefan Oscarson
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Liselotte Öberg
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Andersson, M., Oscarson, S. & Öberg, L. Synthesis of oligosaccharides with oligoethylene glycol spacers and their conversion into glycoconjugates usingN,N,N′,N″-tetramethyl(succinimido)uronium tetrafluoroborate as coupling reagent. Glycoconjugate J 10, 197–201 (1993). https://doi.org/10.1007/BF00702200

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00702200

Keywords

Search

Navigation