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Cell Surface Engineering by a Modified Staudinger Reaction

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Science  17 Mar 2000:
Vol. 287, Issue 5460, pp. 2007-2010
DOI: 10.1126/science.287.5460.2007

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Abstract

Selective chemical reactions enacted within a cellular environment can be powerful tools for elucidating biological processes or engineering novel interactions. A chemical transformation that permits the selective formation of covalent adducts among richly functionalized biopolymers within a cellular context is presented. A ligation modeled after the Staudinger reaction forms an amide bond by coupling of an azide and a specifically engineered triarylphosphine. Both reactive partners are abiotic and chemically orthogonal to native cellular components. Azides installed within cell surface glycoconjugates by metabolism of a synthetic azidosugar were reacted with a biotinylated triarylphosphine to produce stable cell-surface adducts. The tremendous selectivity of the transformation should permit its execution within a cell's interior, offering new possibilities for probing intracellular interactions.

  • * To whom correspondence should be addressed. E-mail: bertozzi{at}cchem.berkeley.edu

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