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Substrate and Donor Specificity of Glycosyl Transferases

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Abstract

It has been shown that all selectins recognize the carbohydrate epitopes sialyl Lewisx and sialyl Lewisa. For the establishment of the structure-activity relationship, the efficient synthesis of these tetrasaccharides and derivatives is therefore of vital interest. The glycosyl transferase-mediated approach is summarized with emphasis on the use of modified acceptors and modified sugar-nucleotide donors. A survey of the involved enzymes: β(1-3) and β(1-4)galactosyl transferases, α(2-3)sialyl transferase, FucT III and FucT VI reveals that the enzymatic synthesis is highly efficient for the rapid preparation of sialyl Lewisx- and sialyl Lewisa-derivatives.

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References

  1. Varki A (1993) Glycobiology 3: 97–130;Witczak ZJ (1995) Curr Med Chem 1: 392–405; Simon PM (1994) Exp Opin Invest Drugs 3: 223–39;McAuliffe JC,HindsgaulO (1997) Chemistry & Industry,170–74.

    Google Scholar 

  2. Karlsson K-A (1995) Curr Opin Struct Biol 5: 622–35; Zopf D (1996) Lancet 347: 1017–21.

    Google Scholar 

  3. Hakomori S-J (1989) Adv Cancer Res 52: 257–331; Dennis JW (1988) Cancer Surveys 7: 753–94.

    Google Scholar 

  4. Welply JK, Keene JL, Schmuke JJ, Howard SC (1994) Biochem Biophys Acta 1197: 215–26.

    Google Scholar 

  5. Stein KE (1994) Int J Technol Assessment in Health Care 10: 167–76.

    Google Scholar 

  6. Sharar SR, Winn RK, Harlan JM (1995) Springer Semin Immunopathol 16: 359–78.

    Google Scholar 

  7. Granger DN, Schmid-Schönbein GW, eds. (1995) Physiology and Pathophysiology of Leukocyte Adhesion New York: Oxford University Press.

    Google Scholar 

  8. Phillips ML, Nudelman E, Gaeta FCA, Perez M, Singhal AK, Hakomori S, Paulson JC (1990) Science 250: 1130–32; Walz G, Aruffo A,KolanusW, Bevilacqua MP, Seed B (1990) Science 250: 1132–35; Bevilacqua MP (1993) Annu Rev Immunol 11: 767–804; McEver RP (1994) Curr Opin Immunol 6: 75–84; Rosen SD, Bertozzi CR (1994) Curr Opin Cell Biol 6: 663–73; Springer TA (1994) Cell 76: 301–14.

    Google Scholar 

  9. Koenig A, Jain R, Vig R, Norgard-Sumnicht KE, Matta KL, Varki A (1997) Glycobiology 7: 79–93.

    Google Scholar 

  10. Magnani JL (1991) Glycobiology 1, 318–20; Berg EL, Robinson MK, Mansson O, Butcher EC, Magnani JL (1991) J Biol Chem 266: 14869–72; Berg EL, Magnani JL, Warnock RA, Robinson MK, Butcher EC (1992) Biochem Biophys Res Commun 184:1048–55.

    Google Scholar 

  11. Scheffler K, Ernst B, Katopodis A, Magnani JL, Wang W-T, Weisemann R, Peters T (1995) Angew Chem Int Ed Engl 34: 1841–44; Scheffler K, Brisson J-R, Weisemann R, Magnani JL, Ernst B, Peters T (1997) J Biomol NMR 9: 423–36; Henrichsen D, Ernst B, Magnani JL, Wang W-T, Meyer B, Peters T (1999) Angew Chem Int Ed.Engl 38: 98–102;Harris R, Kiddle GR, Field RA, Ernst B, Magnani JL, Homans S (1999) J Am Chem Soc 14: 2546–51; JahnkeW,Kolb HC, Blommers MJJ, Magnani JL,Ernst B (1997) Angew Chem Int Ed Engl 36: 2603–7; Kolb HC, Ernst B (1997) Pure Appl Chem 69: 1879–84; Kolb HC, Ernst B (1997) Chem Eur J 3: 1571–78; Hanessian S, Reddy GV,Huynh HK, Pan J, Pedatella S, Kolb HC, Ernst B (1997) Bioorg Med Chem Lett 7: 2729–34; Bänteli R, Ernst B (1997) Tetrahedron Lett 38: 4059–62; Roche D, Bänteli R,Winkler T, Casset F, Ernst B (1998) Tetrahedron Lett 38: 2545–48; Hanessian S, Huynh HK, Reddy GV, McNaughton-Smith G, Ernst B, Kolb HC, Magnani JL, Sweeley C (1998) Bioorg Med Chem Lett 8: 2803–6; Tsai C-Y, Park WKC,Weitz-Schmidt G, Ernst B,Wong C-W(1998) Bioorg Med Chem Lett 8: 2333–38;Norman KE,AndersonGP,KolbHC, Ley K, Ernst B (1998) Blood, 91: 475–83.

    Google Scholar 

  12. Toone EJ, Simon ES, Bednarski MD, Whitesides GM (1989) Tetrahedron 45: 5365–422; David S,Augé C, Gautheron C (1991) Adv Carbohydr Chem Biochem 49: 175–89;Drueckhammer DG, Hennen WJ, Pederson RL, Barbas CF,Gautheron CM, Krach T, Wong C-H (1991) Synthesis 7: 499–525; Ichikawa Y, Look GC, Wong C-H (1992) Anal Biochem 202: 215–21

    Google Scholar 

  13. Hindsgaul O, Palcic MM (1996) Trends Glycosci Glycotechnol 8: 37–49.

    Google Scholar 

  14. Leloir LF (1971) Science 172: 1299–303.

    Google Scholar 

  15. Heidlas JE, Williams KW, Whitesides GM (1992) Acc Chem Res 25: 307–14.

    Google Scholar 

  16. Öhrlein R In Ernst B, Hart G, Sinay P, eds Chemistry and Biology of Carbohydrates: A Comprehensive Handbook. New York: Wiley-VCH (in preparation).

  17. Heidlas JE, Lees WJ, Whitesides GM (1992) J Org Chem 57: 152–57.

    Google Scholar 

  18. YAMASA-Corporation 1-23-8, Nihonbashi-Kagigaracho, Chouku, Tokyo 103, JPN.

  19. Srivastava G, Hindsgaul O, Palcic MM (1993) Carbohydr Res 245: 137–44.

    Google Scholar 

  20. Endo T, Kajihara Y, Kodama H, Hashimoto H (1996) Bioorg Med Chem 4: 1939–48.

    Google Scholar 

  21. Uchiyama T, Hindsgaul O (1998) J Carbohydr Res 17: 1181–90.

    Google Scholar 

  22. Yuasa H, Hindsgaul O, Palcic MM (1992) J Am Chem Soc 114: 5891–92.

    Google Scholar 

  23. Kajihara Y, Endo T, Ogasawara H, Kodama H, Hashimoto H, (1995) Carbohydr Res 269: 273–94.

    Google Scholar 

  24. Jülich Enzyme Products, Germany, offers bulk quantities of CMP-sialic acid on request.

  25. Brossmer R, Gross HJ (1994) Methods Enzymol 247: 153–76.

    Google Scholar 

  26. Chappell MD, Halcomb RL (1997) Tetrahedron 53: 11109–120.

    Google Scholar 

  27. Brossmer R, Gross HJ (1988) Eur J Biochem 177: 583–89.

    Google Scholar 

  28. Martin R, Witte KL, Wong C-H (1998) Bioorg Med Chem 6: 1283–89.

    Google Scholar 

  29. Baisch G, Öhrlein R (1997) Bioorg Med Chem 5: 383–91.

    Google Scholar 

  30. Gokhale UB, Hindsgaul O, Palcic MM (1990) Can J Chem 68: 1063–71.

    Google Scholar 

  31. Binch H, Stangier K, Thiem J (1998) Carbohydr Res 306: 409–19.

    Google Scholar 

  32. Vogel C, Bergemann C, Ott A-J, Lindhorst TK, Thiem J, Dahlhoff WV, Hällgren C, Palcic MM, Hindsgaul O (1997) Liebigs Ann 601–12.

  33. Hällgren C, Hindsgaul O (1995) J Carbohydr Res 14: 453–64.

    Google Scholar 

  34. Srivastava G, Kaur KJ, Hindgaul O, Palcic MM (1992) J Biol Chem 267: 22356–61.

    Google Scholar 

  35. Crawley SC, Palcic MM (1996) In Khan SH, O'Neill RA, eds Modern Methods in Carbohydrate Synthesis. Amsterdam: Harwood Academic Publishers, pp 492–517.

    Google Scholar 

  36. Öhrlein R (1999) Topics in Curr Chem 200: 227–54.

    Google Scholar 

  37. Palcic MM (1994) Methods Enzymol 230: 300–16.

    Google Scholar 

  38. Öhrlein R, Ernst B, Berger EG (1992) Carbohydr Res 236: 335–38.

    Google Scholar 

  39. Ats S-C, Lehmann J, Petry S (1994) Carbohydr Res 252: 325–32.

    Google Scholar 

  40. Baisch G, Öhrlein R (1996) Angew Chem Int Ed Engl 35: 1812–15.

    Google Scholar 

  41. Baisch G, Öhrlein R, Ernst B (1996) Bioorg Med Chem Lett 6: 749–54.

    Google Scholar 

  42. Kren V, Augé C, Sedmera P, Havlìcek V, (1994) J Chem Soc Perkin I, 2481–84.

  43. Schultz M, Kunz H (1993) Tetrahedron Assym 4: 1205–20.

    Google Scholar 

  44. Wong C-H, Schuster M, Wang P, Sears P (1993) J Am Chem Soc 115: 5893–901.

    Google Scholar 

  45. Öhrlein R (1997) Biotrans 97, abstract C10, La Granded Motte, France.

  46. Baisch G, Öhrlein R (1998) Bioorg Med Chem 6: 1673–82.

    Google Scholar 

  47. Schmidt RR, Frische K (1993) Bioorg Med Chem Lett 3: 1747–50.

    Google Scholar 

  48. Hayashi T, Murray BW, Wang R, Wong C-H (1997) Bioorg Med Chem 5: 497–500.

    Google Scholar 

  49. Shaheer HK, Hindsgaul O (1994) In Fukuda M, Hindsgaul O, eds Molecular Glycobiology. Oxford: IRL-Press, pp 206–29.

    Google Scholar 

  50. Baisch G, Öhrlein R, Streiff M, Kolbinger F (1998) Bioorg Med Chem Lett 8: 755–58.

    Google Scholar 

  51. Koszdin KL, Bowen BR (1992) Biochem Biophys Res Commun 187: 152–57; Ge Z, Chan NWC, Palcic MM, Taylor DE (1997) J Biol Chem 272: 21357–63.

    Google Scholar 

  52. Baisch G, Öhrlein R, Katopodis A, Ernst B (1996) Bioorg Med Chem Lett 6: 759–62.

    Google Scholar 

  53. Baisch G, Öhrlein R, Katopodis A, (1997) Bioorg Med Chem Lett 7: 2431–34.

    Google Scholar 

  54. Baisch G, Öhrlein R, Streiff M, Kolbinger F (1998) Bioorg Med Chem Lett 8: 751–54.

    Google Scholar 

  55. Baisch G, Öhrlein R (1998) Carbohydr Res 312: 61–72.

    Google Scholar 

  56. Du M, Hindsgaul O (1996) Carbohydr Res 286: 87–105

    Google Scholar 

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Authors and Affiliations

  1. Institute of Molecular Pharmacy, University of Basel, Totengässlein 3, CH-4057, Basel, Switzerland

    Beat Ernst

  2. Novartis Pharma AG, Department of Transplantation, St. Johann, CH-4002, Basel, Switzerland

    Reinhold Oehrlein

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  1. Beat Ernst
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Ernst, B., Oehrlein, R. Substrate and Donor Specificity of Glycosyl Transferases. Glycoconj J 16, 161–170 (1999). https://doi.org/10.1023/A:1026496714403

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