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Enzymes as Catalysts in Carbohydrate Synthesis

  • Eric J. Toone
  • Yoshihiro Kobori
  • David C. Myles
  • Akio Ozaki
  • Walther Schmid
  • Claus von der Osten
  • Anthony J. Sinskey
  • George M. Whitesides
Part of the Industry-University Cooperative Chemistry Program Symposia book series (IUCC)

Abstract

The field of carbohydrate chemistry is perhaps one of the most thoroughly investigated of all disciplines of chemistry. Thousands of investigators, from the time of Emil Fischer, have probed the structure, function and reactivity of mono-, oligo-, and polysaccharides. Nevertheless, carbohydrate chemistry and biology are currently undergoing a major renaissance. In addition to their well known roles as energy storage vehicles and structural components of cells, carbohydrates are now recognized as vital components in biological recognition phenomena.1–3 The involvement of carbohydrates has been implicated in many biological processes, including cell-cell recognition in growth and differentiation, clearance of aging cells from circulation, and cell sorting and targeting. Cell-surface carbohydrates are specific attachment sites for certain pathogenic viruses, bacteria, and parasites, and for several soluble bacterial toxins.4–7 With the realization of these new roles has come a renewed demand for improved synthetic routes to carbohydrates.

Keywords

Adenylate Kinase Inversion Strategy Acetyl Phosphate Carbohydrate Chemistry Vicinal Diol 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Sharon, N. Complex Carbohydrates; Addison-Wesley: Reading, MA, 1975.Google Scholar
  2. 2.
    Horowitz, M. I.; Pigman, W., Eds. The Glycocongugates, Vol I–II; Academic: New York, 1977–1978.Google Scholar
  3. 3.
    Horowitz, M. I., Ed. The Glycoconjugates, Vol III–IV; Academic: New York, 1982.Google Scholar
  4. 4.
    Schauer, R. Adv. Carbohydr. Chem. Biochem. 1982, 40, 131.PubMedCrossRefGoogle Scholar
  5. 5.
    The Lectins: Properties, Functions and Applications in Biology and Medicine: Liener, I. E.; Sharon, N.; Goldstein, I. J., Eds.; Academic: New York, 1986.Google Scholar
  6. 6.
    Paulson, J. C. In The Receptors; Cohn, P. M., Ed.; Academic: New York, 1985; Vol. 2, p 131.Google Scholar
  7. 7.
    Sairam, M. R. In The Receptors: Cohn, P. M., Ed.; Academic: New York, 1985; Vol. 2, p307Google Scholar
  8. 8.
    Schmidt, R. R. Angew. Chem. Int. Ed. Engl. 1986, 25, 212.CrossRefGoogle Scholar
  9. 9.
    Kunz, H. Angew. Chem. Int. Ed. Engl. 1987, 26, 294.CrossRefGoogle Scholar
  10. 10.
    Paulsen, H. Angew. Chem. Int. Ed. Engl. 1982, 21, 155.CrossRefGoogle Scholar
  11. 11.
    Lemieux, R U. Chem Soc. Rev. 1978, 7, 423.CrossRefGoogle Scholar
  12. 12.
    Toone, E. J.; Simon, E. S.; Bednarski, M. D.; Whitesides, G. M. Tetrahedron 1989, 45, 5365.CrossRefGoogle Scholar
  13. 13.
    Jones, J. B. Tetrahedron 1986, 42, 3351.CrossRefGoogle Scholar
  14. 14.
    Enzymes in Organic Synthesis (Ciba Foundation Symposium 111); Porter, R; Clark, S., Eds.; Pitman: London, 1985.Google Scholar
  15. 15.
    Akiyama, A.; Bednarski, M. D.; Kim, M.-J.; Simon, E. S.; Waldmann, H.; Whitesides, G. M. CHEMTECH 1988, 627.Google Scholar
  16. 16.
    Horecker, L.; Tsolas, O.; Lai, C. Y. In The Enzymes, Boyer, P. D. Ed.; Academic: New York, 1972; Vol. VII. p 213.Google Scholar
  17. 17.
    Bednarski, M. D.; Simon, E. S.; Bischofberger, N.; Fessner, W.-D.; Kim, M.-J.; Lees, W.; Saito, T.; Waldmann, H.; Whitesides, G. M. J. Am. Chem Soc. 1989, 111, 627.CrossRefGoogle Scholar
  18. 18.
    von der Osten, C. H.; Sinskey, A. J.; Barbas, C. F.; Pederson, R. L.; Wang, Y.-F.; Wong, C.-H. J. Am Chem Soc., 1989, 111, 3924.CrossRefGoogle Scholar
  19. 19.
    Borysenko, C; Spaltenstein, A.; Straub, J.; Whitesides, G. M. J. Am. Chem. Soc. 1989, 111, 9275.CrossRefGoogle Scholar
  20. 20.
    Ozaki, A.; Toone, E. J.; von der Osten, C. H.; Sinskey, A. J.; Whitesides, G. M. J. Am Chem. Soc. 1990, submitted for publication.Google Scholar
  21. 21.
    Ghalamor, M. A.; Heath, E. C. J. Biol Chem. 1962, 237, 2427.Google Scholar
  22. 22.
    Effenberger, F.; Straub, A. Tetrahedron Lett. 1987, 28, 1641.CrossRefGoogle Scholar
  23. 23.
    Schmid, W.; Whitesides, G. M. unpublished results.Google Scholar
  24. 24.
    Crans, D. C.; Kazlauskas, R J.; Hirschbein, B. L.; Wong, C.-H.; Abril, O.; Whitesides, G. M. Methods Enzymol 1987, 136, 263.PubMedCrossRefGoogle Scholar
  25. 25.
    Simon, E. S.; Grabowski, S.; Whtiesides, G. M. J. Am Chem Soc., 1989, 111, 8920.CrossRefGoogle Scholar
  26. 26.
    Racker, E. In The Enzymes: Boyer, P. D.; Lardy, H.; Myrbäch, K., Eds.; Academic: New York; 1961; Vol. 5, p 397.Google Scholar
  27. 27.
    Villifranca, J. J.; Axelrod, B. J. Biol Chem, 1971, 246, 3126.Google Scholar
  28. 28.
    Bolte, J.; Demuynck, C.; Samaki, H. Tetrahedron Lett. 1987, 28, 5525.CrossRefGoogle Scholar
  29. 29.
    Mocali, A.; Aldinucci, D.; Paoletti, F. Carbohydr. Res. 1985, 143, 288.CrossRefGoogle Scholar
  30. 30.
    Kobori, Y.; Myles, D.; Whitesides, G. M. unpublished results.Google Scholar
  31. 31.
    Myles, D.; Whitesides, G. M. unpublished results.Google Scholar
  32. 32.
    Paulsen, H. Chem Soc. Rev. 1984, 13, 15.CrossRefGoogle Scholar
  33. 33.
    Haynie, S. L.; Whitesides, G. M. Appl Biotech. Biochem. 1990, 23, 155.CrossRefGoogle Scholar
  34. 34.
    Waldman, H.; Gygax, D.; Bednarski, M. D.; Shangraw, R; Whitesides, G. M. Carbohydr. Res., 1986, 157, c4.CrossRefGoogle Scholar
  35. 35.
    Simon, E. S.; Grabowski, S.; Whitesides, G. M. J. Org. Chem 1990, submitted.Google Scholar
  36. 36.
    Hirschein, B.:.; Mazenod, F. P.; Whtiesides, G. M. J. Org. Chem., 1982, 47, 3765.CrossRefGoogle Scholar
  37. 37.
    Simon, E. S.; Bednarski, M. D.; Whitesides, G. M. Tetrahedron Lett., 1988, 29, 1123.CrossRefGoogle Scholar
  38. 38.
    Enzymatic Bases of Detoxication; Jakoby, W. B. Ed.; Academic: New York, 1980; Vol. II.Google Scholar
  39. 39.
    Zalitis, J.; Feingold, D. S.; Arch. Biochem Biophys. 1969, 12, 457.CrossRefGoogle Scholar
  40. 40.
    Toone, E. J.; Whitesides, G. M. unpublished results.Google Scholar
  41. 41.
    Van Dam, H. E.; Dieboom, A. P. G.; ban Bekkum, H. Appl Catal, 1987, 33, 367.Google Scholar
  42. 42.
    Van Dam, H. E.; Dieboom, A. P. G.; ban Bekkum, H. Appl Catal, 1987, 33, 373.Google Scholar
  43. 43.
    Simon. E. S.; Bednarski, M. D.; Whitesides, G. M. J. Am Chem Soc. 1988, 110, 7159.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1990

Authors and Affiliations

  • Eric J. Toone
    • 1
  • Yoshihiro Kobori
    • 1
  • David C. Myles
    • 1
  • Akio Ozaki
    • 1
  • Walther Schmid
    • 1
  • Claus von der Osten
    • 2
  • Anthony J. Sinskey
    • 2
  • George M. Whitesides
    • 1
  1. 1.Department of ChemistryHarvard UniversityCambridgeUSA
  2. 2.Department of BiologyMassachusetts Institute of TechnologyCambridgeUSA

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