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Synthesis 2023; 55(08): 1172-1186
DOI: 10.1055/s-0042-1751402
DOI: 10.1055/s-0042-1751402
short review
Special Issue Honoring Prof. Guoqiang Lin's Contributions to Organic Chemistry
Recent Advances in Quinone Methide Chemistry for Protein-Proximity Capturing
Startup fund from HUST and Open Fund supported by the State Key Laboratory of Natural and Biomimetic Drugs (K202218).
Dedicated to Professor Guoqiang Lin on the occasion of his 80th birthday.
Abstract
Here we summarize the most recent findings in the chemical-, photo-, or enzyme-triggered generation of nitrogen and oxygen anions leading to the formation of quinone methide intermediates (QMIs). This short review is divided into two categories: generation of nitrogen and oxygen anions. Based on quinone methide intermediates (QMIs), proximate capture of a wide range of proteins has been widely determined and studied. Generally, the triggers include, photoirradiation using 365/254 nm UV light, small molecules (ROS/TBAF/s-tetrazine), metal catalysis (iridium catalysis), and enzymes (NQO1/β-galactosidase). New directions including far-red light, heat, force, microwave, and more practical approaches are explored and illustrated.
1 Introduction
2 Generation of the Nitrogen Anion
3 Generation of the Oxygen Anion
4 Conclusion
Key words
quinone methide chemistry - reactive oxygen species - boronic acid - photoirradiation - NAD(P)H quinone dehydrogenase 1 - β-galactosidase - protein-protein interactionsPublication History
Received: 30 October 2022
Accepted after revision: 01 December 2022
Article published online:
03 January 2023
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