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A synthetic supramolecular system is described that models the effect of ph
osphoryl transfer in molecular recognition. beta-Cyclodextrin-6A-phosphate
(pCD), which is shown to be a substrate of alkaline phosphatase, binds cati
onic aromatic guests, including anticancer agents, up to 100-fold better th
an native beta-CD. The above observations demonstrate that pCD is capable o
f releasing the guests from its cavity upon hydrolysis with the phosphatase
, as also confirmed by monitoring the hydrolysis in the presence of a guest
.