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PubMed · 10720325

Cell surface engineering by a modified Staudinger reaction.

E Saxon·C R Bertozzi
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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.

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AcetylationAzidesBiotinBiotinylationCell MembraneFlow CytometryFluorescent DyesGlycoconjugatesHeLa CellsHexosaminesHumansJurkat CellsKetonesOxidation-ReductionPhosphinesSolubilitySulfhydryl CompoundsJournal ArticleResearch Support, U.S. Gov't, Non-P.H.S.Research Support, U.S. Gov't, P.H.S.

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E Saxon, C R Bertozzi. 2000-03-17. Cell surface engineering by a modified Staudinger reaction.. https://doi.org/10.1126/science.287.5460.2007

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