Mechanism of Phosphodiester Cleavage with ��–Cyclodextrin

Authors

Alvan C. Hengge, Utah State UniversityFollow
W. W. Cleland

Document Type

Article

Journal/Book Title

Journal of Organic Chemistry

Publication Date

1991

Volume

56

First Page

1972

Last Page

1974

Abstract

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 pK_a of 12 and act in some instances as nucleophiles and in some instances as a general base to promote nucleophilic attack by water.

Recommended Citation

A. C. Hengge and W. W. Cleland. “Mechanism of Phosphodiester Cleavage with β–Cyclodextrin.” J. Org. Chem. 1991, 56, 1972-1974.