Science China Chemistry

, Volume 53, Issue 9, pp 1963–1969 | Cite as

Synthesis of 3″- and 4″-deoxy-Lewisx trisaccharides: A useful tool for study of carbohydrate-carbohydrate interaction

  • DengXiang Dong
  • Chafika Gourmala
  • YanYan Zhang
  • YongMin Zhang
Articles

Abstract

Synthesis of 3″-deoxy and 4″-deoxy Lewisx trisaccharides is described. Phenyl 2,3,6-tri-O-benzoyl-4-deoxy-1-thio-β-d-xylo-hexopyranoside was condensed with a diol of glucosamine to give regio- and stereo-selectively a disaccharide. Stereoselective fucosylation of this disaccharide provided a protected deoxy Lewisx trisaccharide which was deprotected to give the 4″-deoxy Lewisx trisaccharide. Application of the similar synthetic sequence provided the 3″-deoxy Lewisx trisaccharide.

Keywords

carbohydrate glycosylation synthesis trisaccharide 

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References

  1. 1.
    Hakomori S. Carbohydrate-to-carbohydrate interaction in basic cell biology: A brief overview. Arch Biochem Biophy, 2004, 426: 173–181CrossRefGoogle Scholar
  2. 2.
    Hakomori S. Carbohydrate-carbohydrate interaction as an initial step in cell recognition. Pure Appl Chem, 1991, 63: 473–482CrossRefGoogle Scholar
  3. 3.
    Yoshida C, Heasman J, Golstone K, Vickers L, Wylie C. Expression of the Lewis group carbohydrate antigens during xenopus development. Glycobiology, 1999, 9: 1323–1330CrossRefGoogle Scholar
  4. 4.
    Eggens I, Fenderson B, Toyokuni T, Dean B, Stroud M, Hakomori S. Specific interaction between Lex and Lex determinants. J Biol Chem, 1989, 264: 9476–9484Google Scholar
  5. 5.
    Kojima N, Fenderson BA, Stroud MR, Goldberg RI, Habermann R, Toyokuni T, Hakomori S. Further studies on cell adhesion based on Lex-Lex interaction, with new approaches: Embryoglycan aggregation of F9 teratocarcinoma cells, and adhesion of various tumour cells based on Lex expression. Glycoconjugate J, 1994, 11: 238–248CrossRefGoogle Scholar
  6. 6.
    Wormald MR, Edge CJ, Dwek RA. The solution conformation of the Lex group. Biochem Biophys Res Commun, 1991, 180: 1214–1221CrossRefGoogle Scholar
  7. 7.
    Henry B, Desvaux H, Pristchepa M, Berthault P, Zhang Y, Mallet JM, Esnault J, Sinaÿ P. NMR study of a Lewisx pentasaccharide derivative: solution structure and interaction with cations. Carbohydr Res, 1999, 315: 48–62CrossRefGoogle Scholar
  8. 8.
    Geyer A, Gege C, Schmidt RR. Carbohydrate-carbohydrate recognition between Lewisx glycoconjugates. Angew Chem Int Ed, 1999, 38: 1466–1468CrossRefGoogle Scholar
  9. 9.
    Geyer A, Gege C, Schmidt RR. Calcium-dependent carbohydrate-carbohydrate recognition between Lewisx blood group antigens. Angew Chem Int Ed, 2000, 39: 3246–3249Google Scholar
  10. 10.
    Gege C, Geyer A, Schmidt RR. Carbohydrate-carbohydrate recognition between Lewis X blood group antigens, mediated by calcium ions. Eur J Org Chem, 2002, 2475–2485Google Scholar
  11. 11.
    Siuzdak G, Ichikawa Y, Caulfield TJ, Munoz B, Wong CH, Nicolaou KC. Evidence of Ca2+-dependent carbohydrate association through ion spray mass-spectrometry. J Am Chem Soc, 1993, 115: 2877–2881CrossRefGoogle Scholar
  12. 12.
    Pincet F, Le Bouar T, Zhang Y, Esnault J, Mallet JM, Perez E, Sinaÿ P. Ultraweak sugar interactions for transient cell adhesion. Biophys J, 2001, 80: 1354–1358CrossRefGoogle Scholar
  13. 13.
    Gourier C, Pincet F, Perez E, Zhang Y, Mallet JM, Sinaÿ P. Specific and non specific interactions involving Lex determinant quantified by lipid vesicle micromanipulation, Glycoconj J, 2004, 21: 165–174CrossRefGoogle Scholar
  14. 14.
    Gourier C, Pincet F, Perez E, Zhang Y, Zhu Z, Mallet JM, Sinaÿ P. The natural Lewisx bearing lipids promote membrane adhesion. Influence of ceramide on carbohydrate-carbohydrate bond formation. Angew Chem Int Ed, 2005, 44: 1683–1687CrossRefGoogle Scholar
  15. 15.
    Tromas C, Rojo J, de la Fuente JM, Barrientos AG, Garcia R, Penadés S. Adhesion forces between Lewisx determinant antigen measured by atomic force microscopy. Angew Chem Int Ed, 2001, 40: 3052–3055CrossRefGoogle Scholar
  16. 16.
    de la Fuente JM, Eaton P, Barrientos AG, Menéndez M, Penadés S. Thermodynamic evidence for Ca2+-mediated self-aggregation of Lewisx gold glyconanoparticles. A model for cell adhesion via carbohydrate-carbohydrate interaction. J Am Chem Soc, 2005, 127: 6192–6197CrossRefGoogle Scholar
  17. 17.
    Hernaiz MJ, de la Fuente JM, Barrientos AG, Penadés S. A model system mimicking glycosphingolipid clusters to quantify carbohydrate self-interactions by surface plasmon resonance. Angew Chem Int Ed, 2002, 41: 1554–1557CrossRefGoogle Scholar
  18. 18.
    Boubelik M, Floryk D, Bohata J, Drabevora L, Macak J, Smid F, Draber P. Lex glycosphingolipids mediated cell aggregation. Glycobiology, 1998, 8: 139–146CrossRefGoogle Scholar
  19. 19.
    Nodet G, Poggi L, Abergel D, Gourmala C, Dong D, Zhang Y, Mallet JM, Bodenhausen G. Weak calcium-mediated interactions between Lewisx-related trisaccharides studied by NMR measurements of residual dipolar couplings. J Am Chem Soc, 2007, 129: 9080–9085CrossRefGoogle Scholar
  20. 20.
    He Y, Johansson M, Sterner O. Mild microwave-assisted hydrolysis of acetals under solvent-free conditions. Synth Commun, 2004, 34: 4153–4158CrossRefGoogle Scholar
  21. 21.
    Guilbert B, Davis NJ, Pearce M, Aplin RT, Flitsch SL. Dibutylstannylene acetals: Useful intermediates for the regioselective sulfation of glycosides. Tetrahedron: Asymmetry, 1994, 5: 2163–2178CrossRefGoogle Scholar
  22. 22.
    Zhang J, Otter A, Bundle DR. Synthesis and conformational studies of the tyvelose capped, Lewis-x like tetrasaccharide epitope of Trichinella spiralis. Bioorg Med Chem, 1996, 4: 1989–2001CrossRefGoogle Scholar
  23. 23.
    Gourmala C, Zhu Z, Luo Y, Fan BT, Ghalem S, Hu Y, Zhang Y. First synthesis of 3′-deoxy Lewisx pentasaccharide. Tetrahedron: Asymmetry, 2005, 16: 3024–3029CrossRefGoogle Scholar
  24. 24.
    Lönn H. Synthesis of a tri- and a hepta-saccharide which contain α-L-fucopyranosyl groups and are part of the complex type of carbohydrate moiety of glycoproteins. Carbohydr Res, 1985, 139: 105–113Google Scholar
  25. 25.
    Stick RV, Stubbs KA. From glycoside hydrolases to thioglycoligases: The synthesis of thioglycosides. Tetrahedron: Asymmetry, 2005, 16: 321–335CrossRefGoogle Scholar

Copyright information

© Science China Press and Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  • DengXiang Dong
    • 1
    • 2
  • Chafika Gourmala
    • 1
  • YanYan Zhang
    • 1
    • 2
  • YongMin Zhang
    • 1
    • 2
  1. 1.Institut Parisien de Chimie Moléculaire, UMR 7201 CNRSUniversité Pierre et Marie Curie-Paris 6ParisFrance
  2. 2.Guiyang College of Traditional Chinese MedicineGuiyangChina

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