bc0c00232_si_001.pdf (7.96 MB)
Precise Installation of Diazo-Tagged Side-Chains on Proteins to Enable In Vitro and In-Cell Site-Specific Labeling
journal contribution
posted on 2020-05-19, 12:09 authored by Barbara Bernardim, Lavinia Dunsmore, He Li, Brad Hocking, Reyes Nuñez-Franco, Claudio D. Navo, Gonzalo Jiménez-Osés, Antonio C. B. Burtoloso, Gonçalo J. L. BernardesThe
chemistry of diazo compounds has generated a huge breadth of
applications in the field of organic synthesis. Their versatility
combined with their tunable reactivity, stability, and chemoselectivity
makes diazo compounds desirable reagents for chemical biologists.
Here, we describe a method for the precise installation of diazo handles
on proteins and antibodies in a mild and specific approach. Subsequent
1,3-cycloaddition reactions with strained alkynes enable both bioimaging
through an in-cell “click” reaction and probing of the
cysteine proteome in cell lysates. The selectivity and efficiency
of these processes makes these suitable reagents for chemical biology
studies.