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. 2012 Dec 19;23(12):2321-8.
doi: 10.1021/bc300410p. Epub 2012 Nov 29.

Formylbenzene diazonium hexafluorophosphate reagent for tyrosine-selective modification of proteins and the introduction of a bioorthogonal aldehyde

Julia Gavrilyuk  1 , Hitoshi Ban, Masanobu Nagano, Wataru Hakamata, Carlos F Barbas 3rd
Affiliations

Formylbenzene diazonium hexafluorophosphate reagent for tyrosine-selective modification of proteins and the introduction of a bioorthogonal aldehyde

Julia Gavrilyuk et al. Bioconjug Chem. .

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.

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Figures

Figure 1
Figure 1
Diazonium-based biotinylation of proteins.
Figure 2
Figure 2
Diazonium-based biotinylation efficiency as a function of pH.
Figure 3
Figure 3
ELISA evaluation of the FBDP modified trastuzumab and binding to ErbB2 and streptavidin.
Figure 4
Figure 4
HeLa cells labeling with FBDP. (a) Schematic representation of the labeling procedure; (b) FITC histogram overlay of unlabeled cells (red), cells treated with 100 uM FBDP (blue) or 10 uM FBDP (green) or 1 uM FBDP (orange); (c) Representative dot plots of cells labeled with 100 uM FBDP (I) and unlabeled cells (II).
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
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