Oligosaccharide recognition using polypyrrolic macrocycles as scaffolds

ORGN 779

Amanda E. Hargrove, aehargrove@cm.utexas.edu, Eric V. Anslyn, anslyn@ccwf.cc.utexas.edu, and Jonathan L. Sessler, sessler@mail.utexas.edu. Department of Chemistry and Biochemistry, University of Texas at Austin, 1 University Station A5300, Austin, TX 78731
Oligosaccharide recognition and sensing can provide valuable insight into several human diseases and may lead to new methods of disease diagnosis. We propose a series of tunable synthetic receptors used in conjunction with selected RNA-aptamers as an efficient and selective system for the recognition and sensing of biologically relevant oligosaccharides. Porphyrin and expanded-porphyrin scaffolds allow for the systematic variation of the number, positions and relative distances of the o-(aminomethyl)phneyl boronic acid recognition units as well as the size and shape of the receptor cavity. The developed synthetic route is based on the condensation of a boronic acid-appended aldehyde with a variety of pyrrole-based precursors to form macrocycles such as those shown here. We are currently testing the saccharide binding properties of such molecules and the use of RNA-aptamers, selected to bind the receptor-saccharide complex, as a method to increase selectivity.