Mechanism of Phosphodiester Cleavage with ��–Cyclodextrin
Journal of Organic Chemistry
Cyclodextrins are cyclic oligomers of glucose with a hydrophobic pocket that form complexes with a range of organic compounds.1 The secondary hydroxyl groups are clustered around one rim of the cavity and have been found to act as catalysts in the hydrolysis of esters, lactams, amides, carbonates, and other compounds.1 These hydroxyls have a pKa of 12 and act in some instances as nucleophiles and in some instances as a general base to promote nucleophilic attack by water.
A. C. Hengge and W. W. Cleland. “Mechanism of Phosphodiester Cleavage with β–Cyclodextrin.” J. Org. Chem. 1991, 56, 1972-1974.