ORGN 642 |
| Orthogonal protecting group strategies have been developed for the generation of sulfated oligosaccharides related to heparan sulfate. A library of heparan sulfate-like disaccharides has been synthesized using six different protecting groups, and a set of deprotection conditions have been developed enabling the selective removal of each group in the presence of sulfate esters. This method has been further applied toward the preparation of sulfated mono- and disaccharides on solid support. Orthogonally protected glucosamines have been loaded onto resin linked by α-(2-hydroxyethyl) units, and subjected to multistep deprotection–sulfation sequences. The sulfated oligosaccharides are then cleaved from the resin and purified by reverse-phase HPLC. In particular, we have investigated the role of the sulfate counterion in subsequent deprotection and cleavage steps, and purification conditions which minimize counterion exchange for reproducible chemical characterization. |
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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 |