1 Aarhus University, Aarhus University2 Faculty of Science, Aarhus University, Aarhus University3 Department of Chemistry, Faculty of Science, Aarhus University, Aarhus University4 Nano-teknologi, Aarhus University, Aarhus University5 unknown
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 beta-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.