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A New, Simple, High-Affinity Glycosidase Inhibitor:  Analysis of Binding through X-ray Crystallography, Mutagenesis, and Kinetic Analysis

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Protein Engineering Network of Centres of Excellence Department of Chemistry, University of British Columbia 2036 Main Mall, Vancouver, Canada, V6T 1Z1 Ontario Cancer Institute and Department of Medical Biophysics University of Toronto, Toronto, Canada, M5G 2M9
Cite this: J. Am. Chem. Soc. 2000, 122, 17, 4229–4230
Publication Date (Web):April 14, 2000
https://doi.org/10.1021/ja0002870
Copyright © 2000 American Chemical Society

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  3. Michael T. Yang and K. A. Woerpel. The Effect of Electrostatic Interactions on Conformational Equilibria of Multiply Substituted Tetrahydropyran Oxocarbenium Ions. The Journal of Organic Chemistry 2009, 74 (2) , 545-553. https://doi.org/10.1021/jo8017846
  4. Milica Tešić, Jacqueline Wicki, David K. Y. Poon, Stephen G. Withers, Donald J. Douglas. Gas phase noncovalent protein complexes that retain solution binding properties: Binding of xylobiose inhibitors to the β-1, 4 exoglucanase from Cellulomonas fimi. Journal of the American Society for Mass Spectrometry 2007, 18 (1) , 64-73. https://doi.org/10.1016/j.jasms.2006.08.012
  5. Ganesh Pandey,, Shrinivas G. Dumbre,, M. Islam Khan, and, M. Shabab. Convergent Approach toward the Synthesis of the Stereoisomers of C-6 Homologues of 1-Deoxynojirimycin and Their Analogues:  Evaluation as Specific Glycosidase Inhibitors. The Journal of Organic Chemistry 2006, 71 (22) , 8481-8488. https://doi.org/10.1021/jo061455v
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  17. Ranjan Kumar Basak, Yashwant D. Vankar. Synthesis and Comparative Study of Homoisofagomines and Analogues as Glycosidase Inhibitors. European Journal of Organic Chemistry 2014, 2014 (4) , 844-859. https://doi.org/10.1002/ejoc.201301279
  18. Momcilo Miljkovic. Conformations and Chemistry of Oxocarbenium Ion. 2014, 87-115. https://doi.org/10.1007/978-1-4614-8268-0_4
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  24. Tina Secher Rasmussen, Henrik Helligsø Jensen. Synthesis and glycosidase inhibitory activity of noeurostegine—a new and potent inhibitor of β-glucoside hydrolases. Org. Biomol. Chem. 2010, 8 (2) , 433-441. https://doi.org/10.1039/B918576C
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  28. M. Bols, Ó. López, F. Ortega-Caballero. Glycosidase Inhibitors: Structure, Activity, Synthesis, and Medical Relevance. 2007, 815-884. https://doi.org/10.1016/B978-044451967-2/00100-8
  29. Ganesh Pandey, Shrinivas G. Dumbre, M. Islam Khan, M. Shabab, Vedavati G. Puranik. A β-lactam-azasugar hybrid as a competitive potent galactosidase inhibitor. Tetrahedron Letters 2006, 47 (45) , 7923-7926. https://doi.org/10.1016/j.tetlet.2006.09.005
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  36. Gavin Pell, Lóránd Szabo, Simon J. Charnock, Hefang Xie, Tracey M. Gloster, Gideon J. Davies, Harry J. Gilbert. Structural and Biochemical Analysis of Cellvibrio japonicus Xylanase 10C. Journal of Biological Chemistry 2004, 279 (12) , 11777-11788. https://doi.org/10.1074/jbc.M311947200
  37. Antoni Planas, Juan Nieto, Mireia Abel, Antoni Segade. Unusual Role of the 3-OH Group of Oligosaccharide Substrates in the Mechanism of Bacillus 1,3-1,4-β-glucanase. Biocatalysis and Biotransformation 2003, 21 (4-5) , 223-231. https://doi.org/10.1080/10242420310001618500
  38. Andrea Vasella, Gideon J Davies, Matthias Böhm. Glycosidase mechanisms. Current Opinion in Chemical Biology 2002, 6 (5) , 619-629. https://doi.org/10.1016/S1367-5931(02)00380-0
  39. Antonella Squarcia, Fabrizio Vivolo, Hans-Georg Weinig, Pietro Passacantilli, Giovanni Piancatelli. Glycal-mediated syntheses of enantiomerically pure polyhydroxylated γ- and δ-lactams. Tetrahedron Letters 2002, 43 (26) , 4653-4655. https://doi.org/10.1016/S0040-4039(02)00852-3
  40. Carl S Rye, Stephen G Withers. Glycosidase mechanisms. Current Opinion in Chemical Biology 2000, 4 (5) , 573-580. https://doi.org/10.1016/S1367-5931(00)00135-6

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