Convergent synthesis of bifunctional glycopeptides bearing differential glycans

ORGN 301

J. David Warren, Justin S. Miller, and Samuel J. Danishefsky. Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10021, and Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, NY 10027
A method is disclosed for the convergent synthesis of multiply glycosylated peptides. The approach centers on a novel technique for generating masked, complex oligosaccharide-containing glycopeptide acyl donors that are activated in situ and used directly in segment coupling with a second complex oligosaccharide-containing glycopeptide, resulting in a completely unprotected, bifunctional glycopeptide. The system demonstrates a minimum level of hydrolysis and epimerization at the C-terminal residue of the acyl donor during fully convergent segment coupling.
 

New Reactions and Methodology
8:00 AM-12:00 PM, Tuesday, August 24, 2004 Pennsylvania Convention Center -- 201A, Oral

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004