Artificial enzymes based on cyclodextrin with phenol as the catalytic group

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 kcat/kuncat 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 pH for the catalysis was found to be approximately pH 8 and the influence of phosphate concentration was investigated.