Encapsulation effects catalysis of the quaternization of quinuclidine

ORGN 748

Byron W. Purse, Arnaud Gissot, gissot@scripps.edu, and Julius Rebek Jr., jrebek@scripps.edu. The Skaggs Institute for Chemical Biology and The Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Rd. MB-26, La Jolla, CA 92037
One concern in the field of molecular encapsulation is the creation of microenvironments analogous to enzyme active sites in which chemical reactions may take place. One such microenvironment is provided by cavitands, which are open-ended vase-shaped host molecules. The self-folding octaamide cavitand shown in the figure forms kinetically stable host-guest complexes with a variety of small molecules including quinuclidine. We have observed a greater than 500 fold increase in the rate of reaction of bromobutane with quinuclidine upon encapsulation. Our most recent results in the investigation of this chemistry will be reported.

 

Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005