Fluorous Solution-Phase Synthesis of Peptides

DESCRIPTION (provided by applicant): Ready access to various oligosaccharides and glycopeptides is crucial for the development of glycobiology and glycomics-the system-wide study of the interactions of oligosaccharides with other biomolecules such as proteins. The long-term goal of the proposed project is to develop a new method for preparative scale syntheses of exceptionally pure oligopeptides, oligosaccharides, and glycopeptides utilizing Fluorous Technologies' proprietary tagging and purification techniques. The specific aims during Phase I of this STTR proposal are: 1) the development of fluorous-fluorenylmethoxycarbonyl (F-Fmoc) solution-phase oligopeptide synthesis (F-Fmoc Strategy); 2) the development of fluorous tag aided oligosaccharide synthesis; and 3) the development of fluorous tag aided oligosaccharide microarrays and multiwell-plate arrays. These developments will lay the foundation for the project's Phase II, which will include (1) parallel synthesis of oligosaccharide and glycopeptide libraries that have been reported to exhibit interesting biological activities such as immunogenicity against cancer cells, (2) development of automated solution-phase oligomer synthesis using a parallel synthesizer, a liquid handler, and an automated fluorous flash chromatography system, and (3) further exploration of fluorous tags for direct compound array production.