Live cell Staudinger ligation: A FRET-based fluorogenic phosphine

BIOL 128

Matthew J Hangauer, hangauer@berkeley.edu and Carolyn R Bertozzi. Department of Chemistry, University of California - Berkeley, Berkeley, CA 94720-1460
The Staudinger ligation is a useful chemical reaction between a modified triarylphosphine and an azide yielding an amide bond linkage. With the ability to metabolically incorporate azides into glycans and proteins in living cells, this ligation has proven useful for tagging azide-bearing biomolecules on the surface of live cells in vitro and in vivo. This poster focuses on the development of a modified triarylphosphine which becomes fluorescent after Staudinger ligation with an azide. It has been shown to directly label azide-bearing biomolecules on the surface of living mammalian cells, whereas all previous phosphine tags have required a secondary detection step. The fluorogenic nature of this phosphine minimizes background fluorescence thereby providing the potential to image dynamic cellular events involving azide-bearing biomolecules in real time in live cells.