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GIycoconjugates

  • Chapter
Essentials of Carbohydrate Chemistry

Part of the book series: Springer Advanced Texts in Chemistry ((SATC))

Abstract

The discovery of a covalent linkage between a carbohydrate and a protein was made in 1938 by Albert Neuberger. He reacted crystalline hen ovalbumin with a proteinase and isolated a low molecular weight glycopeptide and showed that it contained aspartic acid and a saccharide composed of D-mannose and D-glucosamine. Because of the lack of methods at the time for the determination of structures of biological materials, the nature of the linkage between the carbohydrate and the peptide was not determined. Twenty years later, Neuberger returned to the problem and showed that the linkage was an N-glycoside formed between the hemiacetal hydroxyl of N acetyl-D-glucosamine and the nitrogen of the amide group of L-asparagine.

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References

Literature Cited

  1. J. Montreuil, Adv. Carbohydr. Chem. Biochem., 37 (1980) 158–223.

    Google Scholar 

  2. R. Schauer, Adv. Carbohydr. Chem. Biochem., 40 (1982) 132–234.

    Google Scholar 

  3. J. Montreuil, PureAppl.Chem.,42 (1975) 431–437.

    Article  CAS  Google Scholar 

  4. B. Fournet, G. Strecker, J. Montreuil, L. Dorland, J. Haverkamp, J. E G. Vliegenthart, K. Schmid, and J. P. Binette, Biochemistry, 17 (1978) 5206–5214.

    Article  CAS  Google Scholar 

  5. B. Nilsson, N. E. Nordén, and S. Svensson, J. Biol. Chem.,254 (1979) 4545–4553.

    CAS  Google Scholar 

  6. T. Kondo, M. Fukuda, and T. Osawa, Carbohydr. Res., 58 (1977) 405–414.

    Article  CAS  Google Scholar 

  7. J. Baenziger, S. Kornfeld, and S. Kochwa, J. Biol. Chem., 249 (1974) 1889–1896; 1897–1903.

    Google Scholar 

  8. J. Baenziger and S. Kornfeld, J. Biol. Chem., 249 (1974) 7260–7269; 7270–7281.

    CAS  Google Scholar 

  9. T. Krusius, J. Finne, and H. Rauvala, Eur. J. Biochem., 92 (1978) 289–297.

    Article  CAS  Google Scholar 

  10. U. Rutishauser, A. Acheson, A. K. Hall, D. M. Mann, and J. Sunshine, Science,240 (1988) 53–57.

    Article  CAS  Google Scholar 

  11. T. Tai, K. Yamashita, I. Setsuko, and A. Kobata, J. Biol. Chem.,252 (1977) 6687–6694.

    CAS  Google Scholar 

  12. K. Yamashita, Y. Tachibana, and A. Kobata, J. Biol. Chem., 253 (1978) 3862–3869.

    CAS  Google Scholar 

  13. F. Miller, Immunochemistry, 9 (1972) 217–228.

    Article  CAS  Google Scholar 

  14. A. Tsugita and S. Akabori, J. Biochem., 46 (1959) 695–704.

    CAS  Google Scholar 

  15. N. Katsura and E. A. Davidson, Biochim. Biophys. Acta, 121 (1966) 120–127.

    Article  CAS  Google Scholar 

  16. J. C. Paulson, Trends Biol. Sci.,14 (1989) 272–276.

    Article  CAS  Google Scholar 

  17. R. E. Feeney and Y. Yeh, Adv. Protein Chem., 32 (1978) 191–282.

    Article  CAS  Google Scholar 

  18. W. M. Watkins, Science,152 (1966) 172–181.

    Article  CAS  Google Scholar 

  19. V. Ginsberg, Adv. Enzymol., 36 (1972) 131–149.

    Google Scholar 

  20. K. O. Lloyd and E. A. Kabat, Proc. Natl. Acad. Sci. U.S.,61 (1968) 1470–1479.

    Article  CAS  Google Scholar 

  21. R. C. Hughes, Prog. Biophys. Mol. Biol.,26 (1973) 189–268.

    Article  CAS  Google Scholar 

  22. R. SchauerTrends Biol. Sci., 10 (1985) 357–360.

    Article  CAS  Google Scholar 

  23. W. T. Butler and L. W. Cunningham, J. Biol. Chem., 241 (1966) 3882–3888.

    CAS  Google Scholar 

  24. R. Spiro, J. Biol. Chem., 242 (1967) 4813–4823.

    CAS  Google Scholar 

  25. M. Isemura, T. Ikenaka, and Y. Matsushima, J. Biochem., 74 (1973) 11–21.

    CAS  Google Scholar 

  26. T. Biswas and A. K. Mukherjee, Carbohydr. Res., 63 (1978) 173–181.

    Article  CAS  Google Scholar 

  27. D. T. A. Lamport, Nature,216 (1967) 1322–1324.

    Article  CAS  Google Scholar 

  28. D. T. A. Lamport and D. H. Miller, Plant Physiol., 48 (1971) 454–456.

    Article  CAS  Google Scholar 

  29. C-J. Lote and J. B. Weiss, FEBS Lett., 16 (1971) 81–85.

    Article  CAS  Google Scholar 

  30. J. B. Weiss,C.-J. Lote, and H. Bobinski, Nature,234 (1971) 25–26.

    Article  CAS  Google Scholar 

  31. M. A. Krysteva, I. N. Mancheva, and I. D. Dobrew, Eur. J. Biochem., 40 (1973) 155–161.

    Article  CAS  Google Scholar 

  32. W. Fischer, Lipids, 1 (1976) 255–266; I. Ishizuka and T. Yamakawa, J. Biochem., 64 (1968) 13–23.

    Google Scholar 

  33. J. H. Veerkamp, Biochim. Biophys. Acta,273 (1972) 359–367.

    Article  CAS  Google Scholar 

  34. R. Pincelot, Arch. Biochem. Biophys.,159 (1973) 134–142.

    Article  Google Scholar 

  35. Y. Fujino and T. Miyazawa, Biochim. Biophys. Acta, 572 (1979) 442–451.

    Article  CAS  Google Scholar 

  36. H. R Siebertz, E. Hein, M Linscheid, J. Joyard, and R. Douce, Eur. J. Biochem., 101 (1979) 429–438.

    Article  CAS  Google Scholar 

  37. T. Galliard, Phytochemistry, 7 (1968) 1907–1914.

    Article  CAS  Google Scholar 

  38. T. GalliardBiochem. J.,115 (1969) 335–339.

    CAS  Google Scholar 

  39. G. Rouser, G. Kritchevshy, G. Simon, and G. J. Nelson, Lipids,2 (1967) 37–40.

    Article  CAS  Google Scholar 

  40. T. Inoue, S. S. Desmukh, and R. A. Pieringer, J. Biol. Chem., 246 (1971) 5688–5694.

    CAS  Google Scholar 

  41. M. Levine, J. Bain, R. Narasimhan, B. Palmer, A. J. Yates, and R. K. Murray, Biochim. Biophys. Acta, 441 (1976) 134–145.

    Article  CAS  Google Scholar 

  42. B. L. Slomiany, A. Slomiany, and G. B. J. Glass, Eur. J. Biochem.,84 (1978) 53–59.

    Article  CAS  Google Scholar 

  43. B. L. Slomiany, F. B. Smith, and A. Slomiany, Biochim. Biophys. Acta, 574 (1979) 480–486.

    Article  CAS  Google Scholar 

  44. . W. FischerBiochim. Biophys. Acta, 487,(1977) 89–104

    Article  CAS  Google Scholar 

  45. S. G. Wilkinson, Biochim. Biophys. Acta,164(1968)148–156

    Article  CAS  Google Scholar 

  46. S. G. Wilkinson, Biochim. Biophys. Acta,187(1969) 492–500

    Article  CAS  Google Scholar 

  47. E. C. Gotschlich, B. A. Fraser, O. Nishimura, J. B. Robbins, and T.-Y. Liu, J. Biol. Chem., 256 (1981) 8915–8921.

    CAS  Google Scholar 

  48. J. Gmeiner, O. Luderitz, and O. Westphal, Eur. J. Biochem., 7 (1969) 370–379.

    Article  CAS  Google Scholar 

  49. U. Zähringer, B. Lindner, and E. T. Rietschel, Adv. Carbohydr. Chem. Biochem., 50 (1994) 211–276.

    Article  Google Scholar 

  50. W. Weidel, Z. Physiol. Chem., 299 (1955) 253–258.

    Article  CAS  Google Scholar 

  51. E. C. Heath and M. A. Ghalambor, Biochem. Biophys. Res. Commun., 10 (1963) 340–343.

    Article  CAS  Google Scholar 

  52. R. D. Rick and M. J. Osborn, Proc. Nail. Acad. Sci. USA,69 (1972) 3756–3760.

    Article  CAS  Google Scholar 

  53. W. Dröge, O. Luderitz, and O. Westphal, Eur. J. Biochem., 4 (1968) 126–133.

    Article  Google Scholar 

  54. M. Berst, C. G. Hellerquist, B. Lindber, O. Luderitz, S. Svensson, and O. Westphal, Eur. J. Biochem., 11 (1969) 353–359.

    Article  CAS  Google Scholar 

  55. W. Dröge, V. Lehmann, O. Luderitz, and O. Westphal, Eur. J. Biochem., 14 (1970) 175–184.

    Article  Google Scholar 

  56. G. Hammerling, O. Luderitz, and O. Westphal, Eur. J. Biochem., 15 (1970) 48–56.

    Article  CAS  Google Scholar 

  57. G. Hammerling, O. Luderitz, O. Westphal, and P. H. Mäkelä, Eur. J. Biochem., 22 (1971) 331–344.

    Article  CAS  Google Scholar 

  58. V. Lehmann, O. Luderitz, and O. Westphal, Eur. J. Biochem., 21 (1971) 339–347.

    Article  CAS  Google Scholar 

References for Further Study

  • “Primary structure of glycoprotein glycans: basis for the molecular biology of glycoproteins,” J.Montreuil, Adv. Carbohydr. Chem. Biochem., 37 (1980) 158–223.

    Google Scholar 

  • “The carbohydrates of glycoproteins,” A. Kobata, in Biology of Carbohydrates, Vol. 2, Chap. 2, pp. 87–161, (V. Ginsburg and P. W. Robbins, eds.) J. Wiley, New York (1984).

    Google Scholar 

  • “Biosynthesis of glycoproteins: formation of N-linked Oligosaccharides,” M. D. Snider, in Biology of Carbohydrates, Vol. 2, Chap. 3, pp. 163–197, (V. Ginsburg and P. W. Robbins, eds.) J. Wiley, New York (1984).

    Google Scholar 

  • “Biosynthesis of glycoproteins: formation of 0-linked oligosaccharides,” J. E. Sadler, in Biology of Carbohydrates, Vol. 2, Chap. 4, pp. 199–287, J. Wiley, New York (V. Ginsburg and P. W. Robbins, eds.) (1984).

    Google Scholar 

  • “Enzymatic basis for blood groups in man,” V. Ginsburg, Adv. Enzymol., 36 (1972) 131–149.

    CAS  Google Scholar 

  • “Glycophorin A: a model membrane glycoprotein,” H. Furthmayr, in Biology of Carbohydrates, Vol. 1, Chap. 4, pp. 123–197, (V. Ginsburg and P. W. Robbins, eds.) J. Wiley, New York (1981).

    Google Scholar 

  • Glycolipids, New Comprehensive Biochemistry, Vol. 10 (H.Wiegandt, ed.) Elsevier, London (1985).

    Google Scholar 

  • “Glycoproteins: what are the sugar chains for?” J. C. Paulson, Trends Biol. Sci.,14 (1989) 272–276.

    Article  CAS  Google Scholar 

  • “Sialic acids and their role as biological masks,” R. Schauer, Trends Biol. Sci., 10 (1985) 357–360.

    Article  Google Scholar 

  • “The chemistry and biological significance of 3-deoxy-D-manno-2-octulosonic acid (KDO),” F. M. Unger, Adv. Carbohydr. Chem. Biochem., 38 (1981) 324–388.

    Google Scholar 

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  1. Laboratory of Carbohydrate Chemistry and Enzymology Department of Biochemistry and Biophysics, Iowas State University, Ames, IA, 50011, USA

    John F. Robyt

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© 1998 Springer Science+Business Media New York

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Robyt, J.F. (1998). GIycoconjugates. In: Essentials of Carbohydrate Chemistry. Springer Advanced Texts in Chemistry. Springer, New York, NY. https://doi.org/10.1007/978-1-4612-1622-3_9

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  • DOI: https://doi.org/10.1007/978-1-4612-1622-3_9

  • Publisher Name: Springer, New York, NY

  • Print ISBN: 978-1-4612-7220-5

  • Online ISBN: 978-1-4612-1622-3

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