Canadian Science Publishing, Canadian Journal of Chemistry, 4(84), p. 650-658, 2006
DOI: 10.1139/v06-039
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Two cyclodextrin derivatives (1 and 2) were prepared in an attempt to create glycosidase mimics with a general acid catalyst and a nucleophilic carboxylate group. The catalysts 1 and 2 were found to catalyse the hydrolysis of 4-nitrophenyl β-D-glucopyranoside at pH 8.0, but rapidly underwent decomposition with loss of hydrogen cyanide to convert the cyanohydrin to the corresponding aldehyde. The initial rate of the catalysis shows that the cyanohydrin group in these molecules functions as a good catalyst, but that the carboxylate has no positive effect. The decomposition product aldehydes display little or no catalysis. A mechanism for the decomposition is suggested.Key words: biomimicry, enzyme model, kinetics, intramolecular reaction.