Chapter 20: Conformationally restricted glycoside derivatives as mechanistic probes and/or inhibitors of sugar processing enzymes and receptors
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Published:20 Mar 2014
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C. Maaliki, C. Gauthier, O. Massinon, R. Sagar, S. P. Vincent, and Y. Blériot, in Carbohydrate Chemistry: Chemical and Biological Approaches, Volume 40, ed. A. Pilar Rauter, T. Lindhorst, and Y. Queneau, The Royal Society of Chemistry, 2014, vol. 40, ch. 20, pp. 418-444.
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X-ray crystallography and kinetic isotopic effects applied to glycosyl-processing enzymes in complex with their substrates or inhibitors allowed deciphering of the sugar ring conformation at the atomic level. This information, crucial for the development of potent and selective inhibitors of these enzymes, has been extensively exploited to design conformationally restricted sugar analogues. This chapter gives an overview of the main classes of conformationally restricted sugar analogues aimed at interfering with hydrolytic and non-hydrolytic glycosyl-processing enzymes that have been reported in the literature.
