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Lyu Z , Zhao Y , Buuh ZY , Gorman N , Goldman AR , Islam MS , Tang HY , Wang RE
Steric-Free Bioorthogonal Labeling of Acetylation Substrates Based on a Fluorine-Thiol Displacement Reaction
J Am Chem Soc. 2021 Jan 27;143(3) :1341-1347
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Abstract
We have developed a novel bioorthogonal reaction that can selectively displace fluorine substitutions alpha to amide bonds. This fluorine-thiol displacement reaction (FTDR) allows for fluorinated cofactors or precursors to be utilized as chemical reporters, hijacking acetyltransferase-mediated acetylation both in vitro and in live cells, which cannot be achieved with azide- or alkyne-based chemical reporters. The fluoroacetamide labels can be further converted to biotin or fluorophore tags using FTDR, enabling the general detection and imaging of acetyl substrates. This strategy may lead to a steric-free labeling platform for substrate proteins, expanding our chemical toolbox for functional annotation of post-translational modifications in a systematic manner.
Notes
1520-5126 Lyu, Zhigang Orcid: 0000-0002-6903-3965 Zhao, Yue Buuh, Zakey Yusuf Gorman, Nicole Goldman, Aaron R Orcid: 0000-0001-7605-9592 Islam, Md Shafiqul Tang, Hsin-Yao Wang, Rongsheng E Orcid: 0000-0002-5749-7447 Journal Article United States J Am Chem Soc. 2021 Jan 27;143(3):1341-1347. doi: 10.1021/jacs.0c05605. Epub 2021 Jan 12.