Glycoconjugate Journal

, Volume 8, Issue 1, pp 29–37 | Cite as

Structures of the α(1-3)-galactose-containing asparagine-linked glycans of a Lewis lung carcinoma cell subline resistant toAleuria aurantia agglutinin: elucidation by1H-NMR spectroscopy

  • Henri Debray
  • Danuta Dus
  • Jean-Michel Wieruszeski
  • Gérard Strecker
  • Jean Montreuil


Four bi-antennary glycan fractions of theN-acetyllactosamine-type, derived from a Lewis lung carcinoma (LL2) cell subline resistant to theAleuria aurantia agglutinin were studied by 400 MHz1H-NMR spectroscopy. By this method, their antennae were found to be terminated either by α(2-3 or 6)-linkedN-acetylneuraminic acid or α(1-3)-linked galactose residues. The primary structure of glycans of these four glycopeptide or derived oligosaccharide-alditols has been determined in full detail.


1H-NMR asparagine-linked glycans lectin resistance 



N-acetyl group


N-glycolyl group




N-acetylneuraminic acid


N-glycolylneuraminic acid







Con A

concanavalin A


Lens culinaris agglutinin


Aleuria aurantia agglutinin


Wheat germ agglutinin


Ricinus communis agglutinin II


phosphate buffered saline, 0.01m Na2HPO4/0.14m NaCl, pH 7.2


high performance liquid chromatography


Eagle's Minimal Essential Medium


lectin resistant




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  1. 1.
    Smets LA, Van Beek WP (1984)Biochim Biophys Acta 738:238–49.Google Scholar
  2. 2.
    Montreuil J, Debray H, Debeire P, Delannoy P (1983) InStructural Carbohydrates in the Liver, Falk Symposium 34 (Popper H, Reutter W, Köttgen E, Gudat F, eds), pp 239–58. Boston: MTP Press.Google Scholar
  3. 3.
    Hakomori S, Kannagi R (1986)J Nat Cancer Inst 71:231–51.Google Scholar
  4. 4.
    Debray H, Qin Z, Delannoy P, Montreuil J, Dus D, Radzikowski C, Christensen B, Kieler J (1986)Int J Cancer 37:607–11.Google Scholar
  5. 5.
    Dennis JW (1989)Cancer Surveys 7:573–95.Google Scholar
  6. 6.
    Nicolson GL (1982)Biochim Biophys Acta 695:113–76.Google Scholar
  7. 7.
    Yogeeswaran G (1983)Adv Cancer Res 38:289–350.Google Scholar
  8. 8.
    Dus D, Budzynski W, Radzikowski C (1985)Arch Immunol Ther Exp 33:817–23.Google Scholar
  9. 9.
    Dus D, Debray H, Strazadala L, Rak J, Kusnierczyk H, Montreuil J, Radzikowski C (1990)Clin Exp Metastasis 8:277–86.Google Scholar
  10. 10.
    Debray H, Dus D, Hueso P, Radzikowski C, Montreuil J (1990)Clin Exp Metastasis 8:287–98.Google Scholar
  11. 11.
    Debray H, Montreuil J (1989)Carbohydr Res 185:15–26.Google Scholar
  12. 12.
    Oliver GJA, Hemming FW (1975)Biochem J 152:191–9.Google Scholar
  13. 13.
    Muramatsu T, Atkinson PM, Nathenson SG, Ceccarini C (1973)J Mol Biol 80:781–99.Google Scholar
  14. 14.
    Debray H, Pierce-Cretel A, Spik G, Montreuil J (1983) InLectins-Biology, Biochemistry, Clinical Biochemistry (Bøg-Hansen TC, Spengler GA, eds) pp 335–50. Berlin: Walter de Gruyter.Google Scholar
  15. 15.
    Lee YC, Scocca JR (1972)J Biol Chem 247: 5753–8.Google Scholar
  16. 16.
    Hewitt LF (1937)Biochem J 31:360–6.Google Scholar
  17. 17.
    Baenziger JU, Natowicz M (1981)Anal Biochem 112:357–61.Google Scholar
  18. 18.
    Paz Parente J, Cardon P, Leroy Y, Montreuil J, Fournet B, Ricart G (1985)Carbohydr Res 141:41–57.Google Scholar
  19. 19.
    Fournet B, Strecker G, Leroy Y, Montreuil J (1981)Anal Biochem 116:489–502.Google Scholar
  20. 20.
    Kornfeld K, Reitman ML, Kornfeld R (1981)J Biol Chem 256:6633–40.Google Scholar
  21. 21.
    Anderson DR, Atkinson PH, Grimes WJ (1985)Arch Biochem Biophys 243:605–18.Google Scholar
  22. 22.
    Dorland L, Van Halbeek H, Vliegenthart JFG (1984)Biochem Biophys Res Commun 122:859–66.Google Scholar
  23. 23.
    Vliegenthart JFG, Dorland L, Van Halbeek H (1983)Adv Carbohydr Chem Biochem 41:209–374.Google Scholar
  24. 24.
    Galili U, Macher BA, Buehler J, Shohet SB (1985)J Exp Med 162:573–82.Google Scholar
  25. 25.
    Galili U, Clark MR, Shohet SB, Buehler J, Macher BA (1987)Proc Natl Acad Sci USA 84:1369–73.Google Scholar
  26. 26.
    Eckhardt AE, Goldstein IJ (1983)Biochemistry 22:5280–9.Google Scholar
  27. 27.
    Eckhardt AE, Goldstein IJ (1983)Biochemistry 22:5290–7.Google Scholar
  28. 28.
    Geyer, R, Geyer H, Stirm S, Hunsmann G, Schneider J, Dabrowski V, Dabrowski J (1984)Biochemistry 23:5628–37.Google Scholar
  29. 29.
    Shibata S, Peters BP, Roberts DD, Goldstein IJ, Liotta LA (1982)FEBS Lett 142:194–8.Google Scholar
  30. 30.
    Hanfland P, Egge H, Dabrowski V, Kuhn S, Roelcke D, Dabrowski J (1981)Biochemistry 20:5310–19.Google Scholar
  31. 31.
    Elices MJ, Goldstein IJ (1989)J Biol Chem 264:1375–80.Google Scholar
  32. 32.
    Stanley WP, Peters BP, Blake DA, Yep D, Chu EHY, Goldstein IJ (1979)Proc Natl Acad Sci USA 76:303–7.Google Scholar
  33. 33.
    Hull SR, Laine R, Kaizu T, Rodriguez I, Carraway KL (1984)J Biol Chem 259:4866–77.Google Scholar
  34. 34.
    Cummings RD, Kornfeld S (1984)J Biol Chem 259:6253–60.Google Scholar
  35. 35.
    Dennis JW, Laferte S, Fukuda M, Dell A, Carver JP (1986)Eur J Biochem 161:35–73.Google Scholar
  36. 36.
    Santers UV, Desantis R, Hard KJ, Van Kuik JA, Vliegenthart JFG, Won B, Glick MC (1989)Eur J Biochem 181:249–60.Google Scholar

Copyright information

© Chapman and Hall Ltd 1991

Authors and Affiliations

  • Henri Debray
    • 1
  • Danuta Dus
    • 2
  • Jean-Michel Wieruszeski
    • 1
  • Gérard Strecker
    • 1
  • Jean Montreuil
    • 1
  1. 1.Laboratoire de Chimie Biologique, Unité Mixte du CNRS No 111Université des Sciences et Techniques de Lille Flandres-ArtoisVilleneuve d'Ascq CedexFrance
  2. 2.Department of Tumor Immunology, Hirszfeld Institute of Immunology and Experimental TherapyPolish Academy of SciencesWroclawPoland

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