A practical method for purification of cucurbituril[6] by affinity chromatography

ORGN 358

Sanjita Sasmal1, Mantosh K. Sinha2, and Ehud Keinan2. (1) Department of Molecular Biology and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, CA 92037, (2) The Department of Organic Chemistry, Technion-Israel Institute of Technology, The Department of Molecular Biology and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, Haifa, 32000, Israel
Cucurbit[6]uril (CB[6]) 1 is a macrocyclic cavitand comprising of six glycoluril units, which has a cavity that is accessible through two identical carbonyl portals. The rigid structure and the combination of a hydrophobic cavity with polar portals allow these cavitands to host various molecules and cations, rendering the CBs attractive synthetic receptors and useful building blocks of various supramolecular structures. The major drawback for utilization of CB[6] is its purification from the other cyclic and acyclic isomers. A practical method for the separation and purification of cucurbituril (CB) hexamers has been developed in our group. The approach is based on affinity chromatography using a column packed with aminopentylaminomethylated polystyrene beads, which facilitates the general preparation of cucurbituril[6] derivatives.