Abstract
4-Formylbenzene diazonium hexafluorophosphate (FBDP) is a novel bench-stable crystalline diazonium salt that reacts selectively with tyrosine to install a bioorthogonal aldehyde functionality. Model studies with N-acyl-tyrosine methylamide allowed us to identify conditions optimal for tyrosine ligation reactions with small peptides and proteins. FBDP-based conjugation was used for the facile introduction of small molecule tags, poly(ethylene glycol) chains (PEGylation), and functional small molecules onto model proteins and to label the surface of living cells.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemistry
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Amides / chemistry
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Animals
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Biotinylation
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Cattle
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Diazonium Compounds / chemistry*
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HeLa Cells
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Humans
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Hydrogen-Ion Concentration
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Indicators and Reagents / chemistry*
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Models, Molecular
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Oligopeptides / analysis
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Oligopeptides / chemistry*
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Phosphates / chemistry*
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Proteins / analysis
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Proteins / chemistry*
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Staining and Labeling / methods*
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Tyrosine / chemistry*
Substances
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Aldehydes
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Amides
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Diazonium Compounds
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Indicators and Reagents
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Oligopeptides
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Phosphates
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Proteins
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Tyrosine