Cell surface engineering by a modified Staudinger reaction.

Science (New York, N.Y.) (2000-03-17)
E Saxon, C R Bertozzi
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2-(Diphenylphosphino)terephthalic acid 1-methyl 4-pentafluorophenyl diester, 97%
Sigma-Aldrich
N-Azidoacetylglucosamine, Acetylated

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