Skip to main content

The Chameleon of Retaining Glycoside Hydrolases and Retaining Glycosyl Transferases: The Catalytic Nucleophile

  • Chapter
  • 220 Accesses

Summary

This paper addresses the existence and role of a catalytic nucleophile in retaining glycoside hydrolases and retaining glycosyl transferases. Although the former has now been established beyond doubt, such is not the case with the latter. We report reliable procedures for the synthesis of various 2-deoxy-2-fluoro glycosyl nucleoside diphosphates, useful donor analogues for the study of the mechanism of action of retaining glycosyl transferases.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD   109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Wong C-H, Halcomb RL, Ichikawa Y, Kajimoto T (1995) Angew Chem Int Ed Engl 34: 521

    Article  CAS  Google Scholar 

  2. Wong C-H, Halcomb RL, Ichikawa Y, Kajimoto T (1995) Angew Chem Int Ed Engl 34: 412

    Article  CAS  Google Scholar 

  3. Kobata A (1993) Acc Chem Res 26: 319

    Article  CAS  Google Scholar 

  4. Dwek RA (1995) Biochem Soc Trans 23: 1

    CAS  Google Scholar 

  5. Dwek RA (1996) Chem Rev 96: 683

    Article  CAS  Google Scholar 

  6. Sears P, Wong C-H (1998) Chem Commun 1161

    Google Scholar 

  7. Varki A (1993) Glycobiology 3: 97

    Article  CAS  Google Scholar 

  8. Koshland DE (1953) Biol Rev Cambridge Philos Soc 28: 416

    Article  CAS  Google Scholar 

  9. Legler G, Bause E (1973) Carbohydr Res 28: 45

    Article  CAS  Google Scholar 

  10. Sinnott ML (1990) Chem Rev 90: 1171

    Article  CAS  Google Scholar 

  11. Sinnott ML (1993) Bioorg Chem 21: 34

    Article  CAS  Google Scholar 

  12. Varrot A, Schülein M, Pipelier M, Vasella A, Davies GJ (1999) J Am Chem Soc 121: 2621

    Article  CAS  Google Scholar 

  13. Davies GJ, Henrissat B (1995) Structure 3: 853

    Article  CAS  Google Scholar 

  14. Davies GJ, Wilson KS, Henrissat B (1997) Biochem J 321: 557

    CAS  Google Scholar 

  15. Withers SG, Street IP, Bird P, Dolphin DH (1987) J Am Chem Soc 109: 7530

    Article  CAS  Google Scholar 

  16. Withers SG, Street IP (1988) J Am Chem Soc 110: 8551

    Article  CAS  Google Scholar 

  17. Withers SG, Rupitz K, Street IP (1988) J Biol Chem 263: 7929

    CAS  Google Scholar 

  18. McCarter JD, Withers SG (1996) J Am Chem Soc 118: 241

    Article  CAS  Google Scholar 

  19. McCarter JD, Withers SG (1994) Curr Opin Struct Biol 4: 885

    Article  CAS  Google Scholar 

  20. McCarter JD (1995) PhD Thesis, The University of British Columbia

    Google Scholar 

  21. Henrissat B (1991) Biochem J 280: 309

    CAS  Google Scholar 

  22. Henrissat B, Bairoch A (1993) Biochem J 293: 781

    CAS  Google Scholar 

  23. Henrissat B, Bairoch A (1996) Biochem J 316: 695

    Google Scholar 

  24. Heightman TD, Vasella AT (1999) Angew Chem Int Ed 38: 750

    Article  CAS  Google Scholar 

  25. Gebler JC, Aebersold R, Withers SG (1992) J Biol Chem 267: 11126

    CAS  Google Scholar 

  26. Miao S, McCarter JD, Grace ME, Grabowski GA, Aebersold R, Withers SG (1994) J Biol Chem 269: 10975

    CAS  Google Scholar 

  27. Street IP, Kempton JB, Withers SG (1992) Biochemistry 31: 9970

    Article  CAS  Google Scholar 

  28. Braun C, Brayer GD, Withers SG (1995) J Biol Chem 270: 26778

    Article  CAS  Google Scholar 

  29. Withers SG, Aebersold R (1995) Prot Sci 4: 361

    Article  CAS  Google Scholar 

  30. Vocadlo DJ, Davies GJ, Laine R, Withers SG (2001) Nature 412: 835

    Article  CAS  Google Scholar 

  31. Vocadlo DJ, Meyer C, He S, Withers SG (2000) Biochemistry 39: 117

    Article  CAS  Google Scholar 

  32. Numao S, He S, Evjen G, Howard S, Tollersrud OK, Withers SG (2000) FEBS Letters 484: 175

    Article  CAS  Google Scholar 

  33. Mackenzie LF, Wang Q, Warren RAJ, Withers SG (1998) J Am Chem Soc 120: 5583

    Article  CAS  Google Scholar 

  34. Mayer C, Zechel DL, Reid SP, Warren RAJ, Withers SG (2000) FEBS Letters 466: 40

    Article  CAS  Google Scholar 

  35. Adamson J, Foster AB, Hall LD, Johnson RN, Hesse RH (1970) Carbohydr Res 15: 351

    Article  CAS  Google Scholar 

  36. Adamson J, Foster AB, Westwood JH (1971) Carbohydr Res 18: 345

    Article  CAS  Google Scholar 

  37. Diksic M, Jolly D (1986) Carbohydr Res 153: 17

    Article  CAS  Google Scholar 

  38. Burkart MD, Zhang Z, Hung S-C, Wong C-H (1997) J Am Chem Soc 119: 11743

    Article  CAS  Google Scholar 

  39. Ortner J, Albert M, Weber H, Dax K (1999) J Carbohydr Chem 18: 297

    Article  CAS  Google Scholar 

  40. Vincent SP, Burkart MD, Tsai C-Y, Zhang Z, Wong C-H (1999) J Org Chem 64: 5264

    Article  CAS  Google Scholar 

  41. Albert M, Dax K, Ortner J (1998) Tetrahedron 54: 4839

    Article  CAS  Google Scholar 

  42. Stick RV, Watts AG (unpublished results)

    Google Scholar 

  43. Campbell JA, Davies GJ, Bulone V, Henrissat B (1997) Biochem J 326: 929

    CAS  Google Scholar 

  44. Geremia RA, Petroni EA, Ielpi L, Henrissat B (1996) Biochem J 318: 133

    CAS  Google Scholar 

  45. Qiao L, Murray BW, Shimazaki M, Schultz J, Wong C-H (1996) J Am Chem Soc 118: 7653

    Article  CAS  Google Scholar 

  46. Murray BW, Wittmann V, Burkart MD, Hung S-C, Wong C-H (1997) Biochemistry 36: 823

    Article  CAS  Google Scholar 

  47. Murray BW, Takayama S, Schultz J, Wong C-H (1996) Biochemistry 35: 11183

    Article  CAS  Google Scholar 

  48. Cid E, Gomis RR, Geremia RA, Guinovart JJ, Ferrer JC (2000) J Biol Chem 275: 33614

    Article  CAS  Google Scholar 

  49. Davies GJ, Mackenzie L, Varrot A, Dauter M, Brzozowski AM, Schülein M, Withers SG (1998) Biochemistry 37: 11707

    Article  CAS  Google Scholar 

  50. Vrielink A, Ruger W, Driessen HPC, Freemont PS (1994) EMBO J 13: 3413

    CAS  Google Scholar 

  51. Gastinel LN, Cambillau C, Bourne Y (1999) EMBO J 18: 3546

    Article  CAS  Google Scholar 

  52. Charnock SJ, Davies GJ (1999) Biochemistry 38: 6380

    Article  CAS  Google Scholar 

  53. Ünligil UM, Zhou S, Yuwaraj S, Sarkar M, Schachter H, Rini JM (2000) EMBO J 19: 5269

    Article  Google Scholar 

  54. Ha S, Walker D, Shi Y, Walker S (2000) Protein Sci 9: 1045

    Article  CAS  Google Scholar 

  55. Pedersen LC, Tsuchid K, Kitagawa H, Sugahara K, Darden TA, Negishi M (2000) J Biol Chem 275: 34580

    Article  CAS  Google Scholar 

  56. Persson K, Ly HD, Dieckelmann M, Wakarchuk WW, Withers SG, Strynadka NCJ (2001) Nature Struct Biol 8: 166

    Article  CAS  Google Scholar 

  57. Lin A, Mu J, Yang J, Roach PJ (1999) Arch Biochem Biophys 363: 163

    Article  CAS  Google Scholar 

  58. Alonso MD, Lomako J, Lomako WM, Whelan WJ (1995) FASEB J 9: 1126

    CAS  Google Scholar 

  59. Lomako J, Lomako WM, Whelan WJ (1990) BioFactors 2: 251

    CAS  Google Scholar 

  60. Withers SG, MacLennan DJ, Street IP (1986) Carbohydr Res 154: 127

    Article  CAS  Google Scholar 

  61. Wittmann V, Wong C-H (1997) J Org Chem 62: 2144

    Article  CAS  Google Scholar 

  62. Roach PJ (unpublished results)

    Google Scholar 

  63. Gastinel LN, Bignon C, Misra AK, Hindsgaul O, Shaper JH, Joziasse DH (2001) EMBO J 20: 638

    Article  CAS  Google Scholar 

  64. McAuliffe JC, Stick RV (1997) Aust J Chem 50: 193

    Article  CAS  Google Scholar 

  65. Adam MJ (1982) J Chem Soc Chem Commun 730

    Google Scholar 

  66. Wong C-H (1998) Inhibitors of Glycosyl Transferases, WO 98/25940 (USA), 18th June 1998

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2002 Springer-Verlag Wien

About this chapter

Cite this chapter

Stick, R.V., Watts, A.G. (2002). The Chameleon of Retaining Glycoside Hydrolases and Retaining Glycosyl Transferases: The Catalytic Nucleophile. In: Schmid, W., Stütz, A.E. (eds) Timely Research Perspectives in Carbohydrate Chemistry. Springer, Vienna. https://doi.org/10.1007/978-3-7091-6130-2_13

Download citation

  • DOI: https://doi.org/10.1007/978-3-7091-6130-2_13

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-7289-6

  • Online ISBN: 978-3-7091-6130-2

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics