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The synthesis of two per-O-methylated cyclodextrins with one or two α-hydroxypropionitrile groups attached to the secondary rim is described. The two new cyanohydrins are found to catalyse the hydrolysis of 4-nitrophenyl β-D-glucopyranoside in a buffer solution at pH 8.0 with a rate acceleration of up to 1770.
β-Cyclodextrin containing one or two N-linked ortho-N-acetylaminophenols has been synthesized and tested for their properties as artificial glycosidases. Four different para-nitrophenyl glycosides were used as substrates and k cat /k uncat values of up to 381 were found for the di-functionalized products, whereas the mono derivative showed up to 47 times rate enhancement. The optimum...
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