Using water-driven reactions to label peptides, proteins and cells

ORGN 677

Preeti Sejwal, psejwal@syr.edu, Syracuse University, Syracuse, NY 13244, Yongbin Han, yhan03@mailbox.syr.edu, Department of Chemistry, Syracuse University, 1-014 CST 111 College Place, Syracuse, 13244, and Yan-Yeung Luk, yluk@syr.edu, Department of Chemistry; Department of Biomedical and Chemical Engineering, Syracuse University, 1-014 CST, 111 College Place, Syracuse, NY 13244.
Designed organic reactions that proceed in aqueous environment with chemoselectivity are useful, but rare. In this poster, we report a novel protein and cell labeling reagent using designed squarate derivatives, which possess long-term stability and reactivity in water. Based on a recently developed chemoselective reaction driven by the presence of water at pH>8, our reagent compares favorably over commercially available NHS-labeling reagents. The NHS-labeling reagent are known to have a half life of 10 min at 25 0C in pH 7, this newly designed squarate labeling reagent is stable up to at least a week under the same conditions. We demonstrate the high reactivity and stability of this new reagent by labeling peptides, proteins and mammalian cells with biotin.

 

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