scholarly journals Steric-Free Bioorthogonal Labeling of Acetylation Substrates Based on a Fluorine–Thiol Displacement Reaction

2021 ◽  
Vol 143 (3) ◽  
pp. 1341-1347
Author(s):  
Zhigang Lyu ◽  
Yue Zhao ◽  
Zakey Yusuf Buuh ◽  
Nicole Gorman ◽  
Aaron R. Goldman ◽  
...  
2020 ◽  
Author(s):  
Zhigang Lyu ◽  
Yue Zhao ◽  
Zakey Yusuf Buuh ◽  
Nicole Gorman ◽  
Aaron R. Goldman ◽  
...  

ABSTRACTWe 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 al- kyne- 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 (PTMs) in a systematic manner.


2017 ◽  
Vol 56 (31) ◽  
pp. 8992-8997 ◽  
Author(s):  
David R. Spiciarich ◽  
Rosalie Nolley ◽  
Sophia L. Maund ◽  
Sean C. Purcell ◽  
Jason Herschel ◽  
...  

2021 ◽  
Vol 508 ◽  
pp. 230326
Author(s):  
Wenyang Zhou ◽  
Qinghuang Lian ◽  
Xiaokai Huang ◽  
Weiqiang Ding ◽  
Chunhai Jiang ◽  
...  

1959 ◽  
Vol 37 (6) ◽  
pp. 1048-1052 ◽  
Author(s):  
M. Jackson ◽  
L. D. Hayward

In the displacement reaction with sodium iodide in acetic anhydride solution the rates of reaction of four isohexide tosyl esters were compared to that of an O-acetyl-O-tosylisosorbide recently described. The tosyloxy group in the latter compound was replaced rapidly and was therefore in the 5-endo-position, the compound being correctly named 2-O-acetyl-5-O-p-toluenesulphonyl-1,4;3,6-dianhydro-D-glucitol. The product of the reaction was isolated as a crystalline material, and was identified as 2-O-acetyl-5-deoxy-5-iodo-1,4;3,6-dianhydro-L-iditol.


RSC Advances ◽  
2015 ◽  
Vol 5 (25) ◽  
pp. 19409-19417 ◽  
Author(s):  
Xuejiao Yan ◽  
Haiyan Xiong ◽  
Qingguo Bai ◽  
Jan Frenzel ◽  
Conghui Si ◽  
...  

Ultrathin Pd films with one to five atomic layers were decorated on nanoporous gold by underpotential deposition and galvanic displacement.


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