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

Abstract

Conformational energy maps and descriptions of structures at the local minima are presented for the following fragments found in_N_-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 (Imberty_et 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 with_Lathyrus 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.

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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) In_Computer 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

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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
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  2. Marie-Madeleine Delage
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  3. Yves Bourne
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  4. Christian Cambillau
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  5. Serge Pérez
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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

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