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.
Publication types
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Research Support, U.S. Gov't, Non-P.H.S.
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Acetylation
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Azides / chemical synthesis
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Azides / chemistry
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Azides / metabolism*
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Biotin / analogs & derivatives*
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Biotin / chemical synthesis
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Biotin / chemistry
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Biotin / metabolism
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Biotinylation
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Cell Membrane / chemistry*
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Cell Membrane / metabolism*
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Flow Cytometry
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Fluorescent Dyes / metabolism
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Glycoconjugates / metabolism
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HeLa Cells
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Hexosamines / chemical synthesis
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Hexosamines / chemistry
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Hexosamines / metabolism*
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Humans
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Jurkat Cells
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Ketones / metabolism
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Oxidation-Reduction
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Phosphines / chemical synthesis
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Phosphines / chemistry
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Phosphines / metabolism*
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Solubility
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Sulfhydryl Compounds / metabolism
Substances
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4-(2-(2-(2-(biotinylamino)ethoxy)ethoxy)ethoxy)aminocarbonyl-2-diphenylphosphinobenzoic acid
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Azides
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Fluorescent Dyes
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Glycoconjugates
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Hexosamines
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Ketones
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N-azidoacetylmannosamine
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Phosphines
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Sulfhydryl Compounds
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Biotin