Skip to main content
SpringerLink
Log in

Data bank of three-dimensional structures of disaccharides: Part II,N-acetyllactosaminic type N-glycans. Comparison with the crystal structure of a biantennary octasaccharide

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

Abstract

Conformational energy maps and descriptions of structures at the local minima are presented for the following fragments found inN-acetyllactosaminic type glycans of N-glycoproteins: GlcNAcβ(1–2)Man, GlcNAcβ(1–4)Man, GlcNAcβ(1–6)Man, Galβ(1–4)GlcNAc, GlcNAcβ(1–3)Gal, Fucα(1–6)GlcNAc, Fucα(1–3)GlcNAc, Xylβ(1–2)Man, Galβ(1–3)GlcNAc and GlcNAcβ(1–6)Gal. These results are the second part of a data bank on glycoprotein moieties; five disaccharides found in oligomannose type N-glycans were analysed earlier (Imbertyet al., 1990,Glycoconjugate J 7:27–54). In the present study, three to seven minima are found for each dimer. Conformations of disaccharide fragments found in the crystal structure of the complex of a biantennary octasaccharide withLathyrus ochrus lectin are plotted on these energy maps. While the observed conformations are at predicted minima, they are not always at the minimum predicted to have the lowest energy. Further, not all observed conformations are stabilized by the exo-anomeric effect. We conclude that these oligosaccharides are highly flexible.

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

Abbreviations

LOL1:

Lathyrus ochrus isolectin I

References

  1. Imberty A, Gerber S, Tran V, Pérez S (1990)Glycoconjugate J 7:27–54.

    Google Scholar 

  2. Pérez S, Delage MM (1991)Carbohydr Res 212:253–9.

    Google Scholar 

  3. Carver JP, Mandel D, Michnick SW, Imberty A, Bradye JW (1990) InComputer Modeling of Carbohydrate Molecules, ACS Symposium Series 430 (French AD, Brady JW, eds) pp. 266–80. Washington DC: American Chemical Society.

    Google Scholar 

  4. Montreuil J (1980)Adv Carbohydr Chem Biochem 37:157–223.

    Google Scholar 

  5. Fujii T, Nishiura T, Nishikawa A, Miura R, Taniguchi N (1990)J Biol Chem 265:6009–18.

    Google Scholar 

  6. François-Gérard C, Brocteur J, Andre A, Gerday C, Pierce-Cretel A, Montreuil J, Spik G (1980)Blood Transf Immunohaem XXII:579–87.

    Google Scholar 

  7. Mizuochi T, Taniguchi T, Fujikawa K, Titani K, Kobata A (1983)J Biol Chem 258:6020–24.

    Google Scholar 

  8. Krusius T, Finne J, Rauvala H (1978)Eur J Biochem 92:289–300.

    Google Scholar 

  9. Yamamoto K, Tsuji T, Tarutani O, Osawa T (1984)Eur J Biochem 143:133–44.

    Google Scholar 

  10. Fukuda M, Dell A, Fukuda MN (1984)J Biol Chem 259:4782–91.

    Google Scholar 

  11. Takahashi N, Hotta T, Ishihara H, Mori M, Tejima S, Bligny R, Akazawa T, Endo S, Arata Y (1986)Biochemistry 25:388–95.

    Google Scholar 

  12. Bourne Y, Anguille C, Fontecilla-Camps JC, Rougé P, Cambillau C (1990)J Biol Chem 213:211–13.

    Google Scholar 

  13. Bourne Y, Rougé P, Cambillau C (1991)J Biol Chem (in press).

  14. Rougé P, Borrebaeck CAK, Richardson M, Yarwood A (1987)Glycoconjugate J 4:371–8.

    Google Scholar 

  15. Debray H, Rougé P (1984)FEBS Lett 176:120–4.

    Google Scholar 

  16. Bourne Y, Abergel C, Cambillau C, Frey M, Rougé P, Fontecilla-Camps JC (1990)J Mol Biol 214:571–84.

    Google Scholar 

  17. Bourne Y, Rougé P, Cambillau C (1990)J Biol Chem 265:18161–65.

    Google Scholar 

  18. Tvaroska I, Pérez S (1986)Carbohydr Res 149:389–410.

    Google Scholar 

  19. Marchessault RH, Pérez S (1979)Biopolymers 18:2369–74.

    Google Scholar 

  20. IUPAC-IUB Commission on Biochemical Nomenclature (1971)Arch Biochem Biophys 145:405–21.

    Google Scholar 

  21. Pérez S (1978) DSc Thesis, University of Grenoble, France.

    Google Scholar 

  22. Nishida Y, Ohrui H, Meguro H (1984)Tetrahedron Lett 25:1575–78.

    Google Scholar 

  23. Cumming DA, Carver JP (1987)Biochemistry 26:6676–83.

    Google Scholar 

  24. Hori H, Nishida Y, Ohrui H, Meguro H, Uzawa J (1988)Tetrahedron Lett 29:4457–60.

    Google Scholar 

  25. Pogge R, MONGO Program, Lick Observatory, CA, USA. Vax Graphic Station version by Tom Lew, University of Toronto, Canada.

  26. Tran V, Buléon A, Imberty A, Pérez S (1989)Biopolymers 28:679–90.

    Google Scholar 

  27. Imberty A, Pérez S, Tran V (1989)J Comp Chem 11:206–16.

    Google Scholar 

  28. Cumming DA, Shah RN, Krepinsky JJ, Grey AA, Carver JP (1987)Biochemistry 26:6655–63.

    Google Scholar 

  29. Brünger AT, Kuriyan J, Karplus M (1987)Science 235:458–60.

    Google Scholar 

  30. Pérez S, Vergelati C (1987)Polymer Bull 17:141–8.

    Google Scholar 

  31. Bock K, Meyer B, Thiem J (1978)Angew Chem Int Ed Engl 17:447–9.

    Google Scholar 

  32. Cumming DA, Carver JP (1987)Biochemistry 26:6664–76.

    Google Scholar 

  33. Bouwstra JB, Spoelstra EC, de Waard, P, Leeflang BR, Kamerling JP, Vliegenthart JFG (1990)Eur J Biochem 190:113–22.

    Google Scholar 

  34. Thogersen H, Lemieux RU, Bock K, Meyer B (1982)Can J Chem 60:44–57.

    Google Scholar 

  35. Strecker G, Montreuil J (1979)Biochimie 61:1199–246.

    Google Scholar 

  36. Brisson JR, Carver JP (1983)Can J Biochem Cell Biol 61:1067–78.

    Google Scholar 

  37. Paulsen H, Peters T, Sinnwell V, Lebuhn R, Meyer B (1985)Liebigs Ann Chem 489–509.

  38. Meyer B (1990)Topics Curr Chem 154:141–208.

    Google Scholar 

  39. Deisenhofer J (1981)Biochemistry 20:2361–70.

    Google Scholar 

  40. Paulsen H (1990)Angew Chem Int Ed Engl 29:823–39.

    Google Scholar 

  41. Biswas M, Sekharudu YC, Rao VSR (1986)Int J Biol Macromol 8:2–8.

    Google Scholar 

  42. Yan Z-Y, Bush CA (1990)Biopolymers 29:799–811.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratoire de Synthèse Organique, Faculté des Sciences, 2 rue de la Houssinière, F-44072, Nantes cédex 03, France

    Anne Imberty

  2. Laboratoire de Physiochimie des Macromolécules, INRA, BP 527, F-44026, Nantes cédex 03, France

    Marie-Madeleine Delage & Serge Pérez

  3. Laboratoire de Cristallographie et de Cristallisation des Macromolécules Biologiques, Faculté de Médecine Secteur Nord, F-13326, Marseille cédex 15, France

    Yves Bourne & Christian Cambillau

Authors
  1. Anne Imberty
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Marie-Madeleine Delage
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yves Bourne
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Christian Cambillau
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Serge Pérez
    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

Imberty, A., Delage, MM., Bourne, Y. et al. Data bank of three-dimensional structures of disaccharides: Part II,N-acetyllactosaminic type N-glycans. Comparison with the crystal structure of a biantennary octasaccharide. Glycoconjugate J 8, 456–483 (1991). https://doi.org/10.1007/BF00769847

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00769847

Keywords

Search

Navigation