Automated solution-phase iterative synthesis using fluorocarbon tags

ORGN 629

Gisun Park, gsunny39@iastate.edu, Department of Chemistry, Iowa State University, Gilman Hall, Ames, IA 50011 and Nicola L. Pohl, npohl@iastate.edu, Department of Chemistry and the Plant Sciences Institute, Iowa State University, Gilman, Ames, IA 50011.
Automated solid-phase synthesis has been a successful platform for the production of a range of molecules such as nucleic acids and peptides; however, solid-phase approaches require large excesses of building blocks to achieve the high yields required when intermediates cannot be purified. Here we present an alternative automated solution-phase approach to iterative synthesis based on fluorous tags. This method avoids both the large wastes of building blocks and the requirement to carry-through truncation sequences till the end of the syntheses. The challenges in implementing such as automated approach will be presented in the context of the synthesis of polyrhamnose and a variety of other oligosaccharides.
 

Asymmetric Reactions, Combinatorial Chemistry, Molecular Recognition and Self-Assembly, Proteins, Peptides, Amino Acids and Enzyme Inhibitors
8:00 PM-10:00 PM, Wednesday, March 28, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007