Synthesis 2023; 55(08): 1172-1186
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

You F. Gan
a   Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, Hubei 430030, P. R. of China
,
Yuan Y. Li
a   Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, Hubei 430030, P. R. of China
,
Xiao Q. Chen
a   Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, Hubei 430030, P. R. of China
,
Yu Y. Guo
a   Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, Hubei 430030, P. R. of China
,
Rui Wang  ∗
a   Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, Hubei 430030, P. R. of China
b   Shenzhen Huazhong University of Science and Technology Research Institute, Shenzhen, Guangdong 518057, P. R. of China
› Author AffiliationsStartup fund from HUST and Open Fund supported by the State Key Laboratory of Natural and Biomimetic Drugs (K202218).
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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 interactions


Publication History

Received: 30 October 2022

Accepted after revision: 01 December 2022

Article published online:
03 January 2023

© 2023. Thieme. All rights reserved

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