Skip to main content
Log in

Synthesis of methyl α- and β-N-dansyl-d-galactosaminides, probes for the combining sites ofN-acetyl-d-galactosamine-specific lectins

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

Abstract

The synthesis of the methyl α- and β-N-dansyl-d-galactosaminides is described using methyl α,β-2-azido-2-deoxy-d-galactopyranoside as starting material. This was reduced to the corresponding methyl α,β-2-amino-2-deoxy-d-galactopyranoside and then treated with dansyl chloride to yield a mixture of methyl α,β-N-dansyl-d-galactosaminides which was separated into individual anomeric forms by flash chromatography on silica gel. Methyl α-N-dansyl-d-galactosaminide was used as a fluorescent indicator ligand in continuous substitution titrations to determine the association constants of nonchromophoric carbohydrates with theN-acetyl-d-galactosamine specific lectin fromErythrina corallodendron.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

Abbreviations

ECorL:

Erythrina corallodendron lectin

MeαGalNDns:

methyl 2-deoxy-2-(5-dimethylamino-1-naphthalenesulfamido)-α-d-galactopyranoside

MeβGalNDns:

methyl 2-deoxy-2-(5-dimethylamino-1-naphthalenesulfamido)-β-d-galactopyranoside

References

  1. Schepers G, Blatt Y, Himmelspach K, Pecht I (1978)Biochemistry 17:2239–45.

    Google Scholar 

  2. Lartey PA, Derechin M (1979)Prep Biochem 9:85–95.

    Google Scholar 

  3. De Boeck H, Lis H, van Tilbeurgh H, Sharon N, Loontiens FG (1984)J Biol Chem 259:7067–74.

    Google Scholar 

  4. De Boeck H, Loontiens FG, Lis H, Sharon N (1984)Arch Biochem Biophys 234:297–304.

    Google Scholar 

  5. Swamy MJ, Gupta D, Mahanta SK, Surolia A (1991)Carbohydr Res 213:59–67.

    Google Scholar 

  6. Jacquinet J-C, Sinay P (1987)Carbohydr Res 159:229–54.

    Google Scholar 

  7. Shaanan B, Lis H, Sharon N (1991)Science 253:862–6.

    Google Scholar 

  8. Kinzy W, Lis H, Sharon N (1988)14th International Symposium on Carbohydrate Chemistry, Stockholm, p. 358.

  9. De Boeck H, Loontiens FG, De Bruyne CK (1982)Anal Biochem 124:308–13.

    Google Scholar 

  10. De Boeck H, Matta KI, Claeyssens M, Sharon N, Loontiens FG (1983)Eur J Biochem 131:453–60.

    Google Scholar 

  11. Lis H, Joubert FJ, Sharon N (1985)Phytochemistry 24:2803–9.

    Google Scholar 

  12. Still WC, Kahn M, Mitra A (1978)J Org Chem 43:2923–5.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Dedicated to Hilde De Boeck (1958–1991).

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kinzy, W.R., Belenky, D.M., Loontiens, F.G. et al. Synthesis of methyl α- and β-N-dansyl-d-galactosaminides, probes for the combining sites ofN-acetyl-d-galactosamine-specific lectins. Glycoconjugate J 9, 225–227 (1992). https://doi.org/10.1007/BF00731133

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00731133

Keywords

Navigation