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
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Wong C-H, Halcomb RL, Ichikawa Y, Kajimoto T (1995) Angew Chem Int Ed Engl 34: 521
Wong C-H, Halcomb RL, Ichikawa Y, Kajimoto T (1995) Angew Chem Int Ed Engl 34: 412
Kobata A (1993) Acc Chem Res 26: 319
Dwek RA (1995) Biochem Soc Trans 23: 1
Dwek RA (1996) Chem Rev 96: 683
Sears P, Wong C-H (1998) Chem Commun 1161
Varki A (1993) Glycobiology 3: 97
Koshland DE (1953) Biol Rev Cambridge Philos Soc 28: 416
Legler G, Bause E (1973) Carbohydr Res 28: 45
Sinnott ML (1990) Chem Rev 90: 1171
Sinnott ML (1993) Bioorg Chem 21: 34
Varrot A, Schülein M, Pipelier M, Vasella A, Davies GJ (1999) J Am Chem Soc 121: 2621
Davies GJ, Henrissat B (1995) Structure 3: 853
Davies GJ, Wilson KS, Henrissat B (1997) Biochem J 321: 557
Withers SG, Street IP, Bird P, Dolphin DH (1987) J Am Chem Soc 109: 7530
Withers SG, Street IP (1988) J Am Chem Soc 110: 8551
Withers SG, Rupitz K, Street IP (1988) J Biol Chem 263: 7929
McCarter JD, Withers SG (1996) J Am Chem Soc 118: 241
McCarter JD, Withers SG (1994) Curr Opin Struct Biol 4: 885
McCarter JD (1995) PhD Thesis, The University of British Columbia
Henrissat B (1991) Biochem J 280: 309
Henrissat B, Bairoch A (1993) Biochem J 293: 781
Henrissat B, Bairoch A (1996) Biochem J 316: 695
Heightman TD, Vasella AT (1999) Angew Chem Int Ed 38: 750
Gebler JC, Aebersold R, Withers SG (1992) J Biol Chem 267: 11126
Miao S, McCarter JD, Grace ME, Grabowski GA, Aebersold R, Withers SG (1994) J Biol Chem 269: 10975
Street IP, Kempton JB, Withers SG (1992) Biochemistry 31: 9970
Braun C, Brayer GD, Withers SG (1995) J Biol Chem 270: 26778
Withers SG, Aebersold R (1995) Prot Sci 4: 361
Vocadlo DJ, Davies GJ, Laine R, Withers SG (2001) Nature 412: 835
Vocadlo DJ, Meyer C, He S, Withers SG (2000) Biochemistry 39: 117
Numao S, He S, Evjen G, Howard S, Tollersrud OK, Withers SG (2000) FEBS Letters 484: 175
Mackenzie LF, Wang Q, Warren RAJ, Withers SG (1998) J Am Chem Soc 120: 5583
Mayer C, Zechel DL, Reid SP, Warren RAJ, Withers SG (2000) FEBS Letters 466: 40
Adamson J, Foster AB, Hall LD, Johnson RN, Hesse RH (1970) Carbohydr Res 15: 351
Adamson J, Foster AB, Westwood JH (1971) Carbohydr Res 18: 345
Diksic M, Jolly D (1986) Carbohydr Res 153: 17
Burkart MD, Zhang Z, Hung S-C, Wong C-H (1997) J Am Chem Soc 119: 11743
Ortner J, Albert M, Weber H, Dax K (1999) J Carbohydr Chem 18: 297
Vincent SP, Burkart MD, Tsai C-Y, Zhang Z, Wong C-H (1999) J Org Chem 64: 5264
Albert M, Dax K, Ortner J (1998) Tetrahedron 54: 4839
Stick RV, Watts AG (unpublished results)
Campbell JA, Davies GJ, Bulone V, Henrissat B (1997) Biochem J 326: 929
Geremia RA, Petroni EA, Ielpi L, Henrissat B (1996) Biochem J 318: 133
Qiao L, Murray BW, Shimazaki M, Schultz J, Wong C-H (1996) J Am Chem Soc 118: 7653
Murray BW, Wittmann V, Burkart MD, Hung S-C, Wong C-H (1997) Biochemistry 36: 823
Murray BW, Takayama S, Schultz J, Wong C-H (1996) Biochemistry 35: 11183
Cid E, Gomis RR, Geremia RA, Guinovart JJ, Ferrer JC (2000) J Biol Chem 275: 33614
Davies GJ, Mackenzie L, Varrot A, Dauter M, Brzozowski AM, Schülein M, Withers SG (1998) Biochemistry 37: 11707
Vrielink A, Ruger W, Driessen HPC, Freemont PS (1994) EMBO J 13: 3413
Gastinel LN, Cambillau C, Bourne Y (1999) EMBO J 18: 3546
Charnock SJ, Davies GJ (1999) Biochemistry 38: 6380
Ünligil UM, Zhou S, Yuwaraj S, Sarkar M, Schachter H, Rini JM (2000) EMBO J 19: 5269
Ha S, Walker D, Shi Y, Walker S (2000) Protein Sci 9: 1045
Pedersen LC, Tsuchid K, Kitagawa H, Sugahara K, Darden TA, Negishi M (2000) J Biol Chem 275: 34580
Persson K, Ly HD, Dieckelmann M, Wakarchuk WW, Withers SG, Strynadka NCJ (2001) Nature Struct Biol 8: 166
Lin A, Mu J, Yang J, Roach PJ (1999) Arch Biochem Biophys 363: 163
Alonso MD, Lomako J, Lomako WM, Whelan WJ (1995) FASEB J 9: 1126
Lomako J, Lomako WM, Whelan WJ (1990) BioFactors 2: 251
Withers SG, MacLennan DJ, Street IP (1986) Carbohydr Res 154: 127
Wittmann V, Wong C-H (1997) J Org Chem 62: 2144
Roach PJ (unpublished results)
Gastinel LN, Bignon C, Misra AK, Hindsgaul O, Shaper JH, Joziasse DH (2001) EMBO J 20: 638
McAuliffe JC, Stick RV (1997) Aust J Chem 50: 193
Adam MJ (1982) J Chem Soc Chem Commun 730
Wong C-H (1998) Inhibitors of Glycosyl Transferases, WO 98/25940 (USA), 18th June 1998
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights 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