Open AccessPrecise Installation of Diazo-Tagged Side-Chains on Proteins to Enable In Vitro and In-Cell Site-Specific Labeling
Author(s) -
Barbara Bernardim,
Lavinia Dunsmore,
He Li,
Brad J. W. Hocking,
Reyes NúñezFranco,
Claudio D. Navo,
Gonzalo JiménezOsés,
Antonio C. B. Burtoloso,
Gonçalo J. L. Bernardes
Publication year - 2020
Publication title -
bioconjugate chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.279
H-Index - 172
eISSN - 1520-4812
pISSN - 1043-1802
DOI - 10.1021/acs.bioconjchem.0c00232
Subject(s) - diazo , chemistry , chemoselectivity , reagent , combinatorial chemistry , reactivity (psychology) , chemical biology , click chemistry , cycloaddition , bioorthogonal chemistry , cysteine , proteome , organic chemistry , biochemistry , enzyme , catalysis , alternative medicine , medicine , pathology
The 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.
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