Glycosylation employing bio-systems: from enzymes to whole cells

(Note: The full text of this document is currently only available in the PDF Version )

Vladimír Křen and Joachim Thiem


Abstract

This contribution will highlight chemoenzymatic approaches to the rather complex task of stereospecific and regiospecific glycosylation. Advantages and problems associated with the application of enzymes from carbohydrate metabolism as organic reagents in aqueous and non-aqueous solvent systems are discussed. One chapter will report on the use of glycosidases in reverse hydrolysis and tranglycosylation reactions. Another section focuses on the syntheses with simple as well as more complex and delicate glycosyl-transferases including cofactor regeneration. Further, effective combination of both degrading and synthesising enzyme systems, and finally glycosylations employing cells with direct access to their complete enzyme equipment are treated.


References

  1. C.-H. Wong and G. M. Whitesides, Enzymes in Synthesis Organic Chemistry, Tetrahedron Org. Chem. Ser., ed. J. E. Baldwin and P. D. Magnus, Pergamon, 1994, vol. 12, and references therein. Search PubMed.
  2. D. H. G. Crout, D. A. MacManus and P. Critchley, J. Chem. Soc., Perkin Trans. 1, 1990, 1865 Search PubMed.
  3. Y. Ooi, T. Hashimoto, N. Mitsuo and T. Satoh, Chem. Pharm. Bull., 1985, 33, 1808 Search PubMed.
  4. S. Attal, S. Bay and D. Cantacuzene, Tetrahedron, 1993, 48, 9251 Search PubMed.
  5. V. Křen, Curr. Chem., 1997, 186, 45 Search PubMed and references therein..
  6. E. Rajnochová, J. Dvořáková, Z. Huňkoivá and V. Křen, Biotechnol. Lett., 1997, 19, 869 Search PubMed.
  7. Y. Okahata and T. Mori, J. Chem. Soc., Perkin Trans. 1, 1996, 2861 Search PubMed.
  8. J. Thiem and B. Sauerbrei, Angew. Chem., Int. Ed. Engl., 1991, 30, 1503 Search PubMed.
  9. S. C. T. Svensson and J. Thiem, Carbohydr. Res., 1990, 200, 391 Search PubMed.
  10. K. G. I. Nilsson, Carbohydr. Res., 1987, 167, 95 Search PubMed; K. G. I. Nilsson, Carbohydr. Res., 1988, 180, 53 Search PubMed.
  11. K. Ajisaka, H. Fujimoto and M. Isomura, Carbohydr. Res., 1994, 259, 103 Search PubMed , and the references therein..
  12. V. Křen and J. Thiem, Angew. Chem., Int. Ed. Engl., 1995, 34, 893 Search PubMed.
  13. R. T. Brown, N. E. Carter, F. Scheinmann and N. J. Turner, Tetrahedron Lett., 1995, 36, 1117 Search PubMed.
  14. W. Boos, J. Lehmann and K. Wallenfels, Carbohydr. Res., 1968, 7, 381 Search PubMed.
  15. F. B. Björkling and S. E. Gotfredsen, Tetrahedron, 1988, 44, 2957 Search PubMed.
  16. B. Werschkun, W. A. König, V. Křen and J. Thiem, J. Chem. Soc., Perkin Trans. 1, 1995, 2459 Search PubMed.
  17. S. Tsuji, J. Biochem., 1996, 120, 1 Search PubMed.
  18. C.-H. Wong, S. L. Haynie and G. M. Whitesides, J. Org. Chem., 1982, 47, 5416 Search PubMed.
  19. J. Thiem and T. Wiemann, Angew. Chem., Int. Ed. Engl., 1991, 30, 1163 Search PubMed.
  20. Y. Nishida, T. Wiemann, V. Sinnwell and J. Thiem, J. Am. Chem. Soc., 1993, 115, 2536 Search PubMed.
  21. T. Wiemann, Y. Nishida, V. Sinnwell and J. Thiem, J. Org. Chem., 1994, 59, 6744 Search PubMed.
  22. K. Stangier, M. M. Palcic, D. R. Brundle, O. Hindsgaul and J. Thiem, Carbohydr. Res., in press Search PubMed.
  23. Y. Suzuki and K. Suzuki, Agric. Biol. Chem., 1991, 55, 181 Search PubMed.
  24. S. Kitao and H. Sekine, Biosci. Biotech. Biochem., 1994, 58, 419 Search PubMed.
  25. B. Evers, P. Mischnick and J. Thiem, Carbohydr. Res., 1994, 262, 335 Search PubMed.
  26. U. Kragl, M. Kittelmann, O. Gisalba and C. Wandrey, Ann. N. Y. Acad. Sci., 1995, 750, 300 Search PubMed.
  27. M. Ichikawa, R. L. Schnaar and Y. Ichikawa, Tetrahedron Lett., 1995, 36, 8731 Search PubMed.
  28. Y. Ito and J. C. Paulson, J. Am. Chem. Soc., 1993, 115, 7862 Search PubMed.
  29. B. R. Petuch, B. Arison, A. Hsu, R. Monaghan, F. J. Dumont and T. S. Chen, J. Industrial Microbiol., 1994, 13, 131 Search PubMed.
  30. I. A. Mikhailopulo, A. I. Zinchenko, Z. Kazimierczuk, V. N. Barai, S. B. Bokut and E. N. Kalinichenko, Nucleosides Nucleotides, 1993, 12, 417 Search PubMed.
  31. Y. Umetani, E. Kodakari, T. Yamamura, S. Tanaka and M. Tabata, Plant Cell Reports, 1990, 9, 325 Search PubMed.
  32. M. Ushiyama and T. Furuya, Phytochemistry, 1989, 28, 3009 Search PubMed.
  33. V. Křen, A. Minghetti, P. Sedmera, V. Havlíček, V. Přikrylová and N. Crespi-Perellino, Phytochemistry, 1997, in press Search PubMed.
  34. S. Kamel, M. Brazier, G. Desmet, M.-A. Fliniaux and A. Jacquin-Dubreuil, Photochemistry, 1992, 31, 1581 Search PubMed.
  35. Y. Suzuki, Y. Inada and K. Uchida, Phytochemistry, 1986, 25, 2049 Search PubMed.
  36. R. Osborne, P. Thompson, S. Joel, D. Trew, N. Patel and M. Slevin, Br. J. Clin. Pharmacol., 1992, 34, 130 Search PubMed.
  37. T. A. Aasmundstad, Å. Ripel, E. Bodd, A. Bjørneboe and J. Møland, Biochem. Pharmacol., 1993, 46, 961 Search PubMed.
  38. W. H. Fishman, Method Enzymol., 1957, 3, 55 Search PubMed.