Distortion of a cellobio-derived isofagomine highlights the potential conformational itinerary of inverting β-glucosidases

Chemical Communications

Volumn 3, Issue 8, 2003, Pages 946-947

  Varrot, Annabelle ^a   Macdonald, James ^b   Stick, Robert V ^b   Pell, Gavin ^c   Gilbert, Harry J ^c   Davies, Gideon J ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

^c NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BETA GLUCOSIDASE; CELLULOSE 1,4 BETA CELLOBIOSIDASE; GLYCOSIDASE INHIBITOR; ISOFAGOMINE GLYCOSIDASE INHIBITOR; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; BINDING AFFINITY; CATALYSIS; CHEMICAL STRUCTURE; CONFORMATION; DRUG DESIGN; HYDROLYSIS; STRUCTURE ANALYSIS;

EID: 0037459995     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/b301592k     Document Type: Article

References (14)

1. G. Davies, M. L. Sinnott and S. G. Withers, in Comprehensive Biological Catalysis, ed. M. L. Sinnott, Academic Press, London, 1997, vol. 1, p. 119
2. J. M. Macdonald, R. V. Stick, D. M. G. Tilbrook, S. G. Withers: Aust. J. Chem., 2002, 55, 747
3. J.-Y. Zou, G. J. Kleywegt, J. Ståhlberg, H. Driguez, W. Nerinckx, M. Claeyssens, A. Koivula, T. T. Teeri, T. A. Jones: Structure, 1999, 7, 1035
4. A. Varrot, T. Frandsen, H. Driguez, G. J. Davies: Acta Crystallogr., Sect. D, 2002, 58, 2201
5. A. Varrot, M. Schülein, G. J. Davies: Biochemistry, 1999, 38, 8884
6. A. Koivula, L. Ruohonen, G. Wohlfahrt, T. Reinikainen, T. T. Teeri, K. Piens, M. Claeyssens, M. Weber, A. Vasella, D. Becker, M. L. Sinnott, J. Y. Zou, G. J. Kleywegt, M. Szardenings, J. Stahlberg, T. A. Jones: J. Am. Chem. Soc., 2002, 124, 10015
7. R. Wolfenden, X. Lu, G. Young: J. Am. Chem. Soc., 1998, 120, 6814
8. G. J. Davies, V. M.-A. Ducros, A. Varrot, D. L. Zechel: Biochem. Soc. Trans., 2003, in press
9. V. Ducros, D. L. Zechel, G. N. Murshudov, H. J. Gilbert, L. Szabo, D. Stoll, S. G. Withers, G. J. Davies: Angew. Chem., Int. Ed., 2002, 41, 2824
10. M. N. Namchuk, S. G. Withers: Biochemistry, 1995, 34, 16194
11. D. M. A. Guerin, M. B. Lascombe, M. Costabel, H. Souchon, V. Lamzin, P. Beguin, P. M. Alzari: J. Mol. Biol., 2002, 316, 1061
12. E. Sabini, G. Sulzenbacher, M. Dauter, Z. Dauter, P. L. Jørgensen, M. Schülein, C. Dupont, G. J. Davies, K. S. Wilson: Chem. Biol., 1999, 6, 483
13. S. G. Withers, M. Namchuk and R. Mosi, Potent glycosidase inhibitors: transition state mimics or simply fortuitous binders?, in Iminosugars as glycosidase inhibitors: nojirimycin and beyond, ed. A. E. Stutz, Wiley-VCH, Weinheim, 1999, p. 188
14. J. F. Stoddart, Stereochemistry of Carbohydrates, Wiley Interscience, Toronto, 1971