Recent Advances in Quinone Methide Chemistry for Protein-Proximity Capturing

You F. Gan; Yuan Y. Li; Xiao Q. Chen; Yu Y. Guo; Rui Wang

doi:10.1055/s-0042-1751402

Synthesis, Table of Contents

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

^aHubei 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

^aHubei 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

^aHubei 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

^aHubei 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 ∗

^aHubei 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

^bShenzhen Huazhong University of Science and Technology Research Institute, Shenzhen, Guangdong 518057, P. R. of China

› Author Affiliations

Abstract

All articles of this category

Dedicated to Professor Guoqiang Lin on the occasion of his 80^th 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

Full Text

References

References
1 Reactive Intermediate Chemistry . Moss RA, Platz MS, Jones MJr. John Wiley & Sons; Hoboken: 2004
2 Yan M, Lo JC, Edwards JT, Baran PS. J. Am. Chem. Soc. 2016; 138: 12692
3 Taylor RJ, Geeson MB, Journeaux T, Bernardes GJ. L. J. Am. Chem. Soc. 2022; 144: 14404
4 Nachtsheim BJ. Nat. Chem. 2020; 12: 326
5 Gnaim S, Shabat D. Acc. Chem. Res. 2014; 47: 2970
6 Bai WJ, David JG, Feng Z.-G, Weaver MG, Wu KL, Pettus TR. R. Acc. Chem. Res. 2014; 47: 3655
7 Purdy TN, Moore BS, Lukowski AL. J. Nat. Prod. 2022; 85: 688
8 Doyon TJ, Perkins JC, Baker Dockrey SA, Romero EO, Skinner KC, Zimmerman PM, Narayan AR. H. J. Am. Chem. Soc. 2019; 141: 20269
9 Liu HY, Luo HX, Xue Q, Qin S, Qiu S, Liu SB, Lin J, Li JP, Chen PR. J. Am. Chem. Soc. 2022; 144: 5517
10 Payne NC, Maksoud S, Tannous BA, Mazitschek R. Cell Chem. Biol. 2022; 29: 1333
11 Huang ZY, Liu ZQ, Xie X, Zeng RX, Chen ZJ, Kong LH, Fan XY, Chen PR. J. Am. Chem. Soc. 2021; 143: 18714
12 Iwashita H, Castillo E, Messina MS, Swanson RA, Chang CJ. Proc. Natl. Acad. Sci. U.S.A. 2021; 118: e2018513118
13 Jiménez-Moreno E, Guo ZJ, Oliveira BL, Albuquerque IS, Kitowski A, Guerreiro A, Boutureira O, Rodrigues T, Jiménez-Osés G, Bernardes GJ. L. Angew. Chem. Int. Ed. 2017; 56: 243
14 Doura T, Kamiya M, Obata F, Yamaguchi Y, Hiyama TY, Matsuda T, Fukamizu A, Noda M, Miura M, Urano Y. Angew. Chem. Int. Ed. 2016; 55: 9620
15 Chiba M, Kamiya M, Tsuda-Sakurai K, Fujisawa Y, Kosakamoto H, Kojima R, Miura M, Urano Y. ACS Cent. Sci. 2019; 5: 1676
16 Ito H, Kawamata Y, Kamiya M, Tsuda-Sakurai K, Tanaka S, Ueno T, Komatsu T, Hanaoka K, Okabe S, Miura M, Urano Y. Angew. Chem. Int. Ed. 2018; 57: 15702
17 Liu J, Cai L, Sun W, Cheng R, Wang N, Jin L, Rozovsky S, Seiple IB, Wang L. Angew. Chem. Int. Ed. 2019; 58: 18839
18 Liu J, Cheng R, Van Eps N, Wang N, Morizumi T, Ou WL, Klauser PC, Rozovsky S, Ernst OP, Wang L. J. Am. Chem. Soc. 2020; 142: 17057
19 Liu J, Li S, Aslam NA, Zheng F, Yang B, Cheng R, Wang N, Rozovsky S, Wang PG, Wang Q, Wang L. J. Am. Chem. Soc. 2019; 141: 9458
20 Chiang Y, Kresge AJ, Zhu Y. J. Am. Chem. Soc. 2002; 124: 6349
21 Zhou QB, Turnbull KD. J. Org. Chem. 2001; 66: 7072
22 Tang Q, Liu L, Guo Y, Zhang X, Zhang S, Jia Y, Du Y, Cheng B, Yang L, Huang Y, Chen X. Angew. Chem. Int. Ed. 2022; 61: e202113929
23 Liang CJ, Zheng QZ, Luo TL, Cai WQ, Mao LQ, Wang M. CCS Chem. 2022; 4: 3809 ; DOI: 10.31635/ccschem.022.202101529
24 Park SY, Yoon SA, Lee MH. Bull. Korean Chem. Soc. 2021; 42: 119
25 Cheng ZM, Valença WO, Dias GG, Scott J, Barth ND, de Moliner F, Souza GB. P, Mellanby RJ, Vendrell M, da Silva Júnior EN. Bioorg. Med. Chem. 2019; 27: 3938
26 Gu JA, Mani V, Huang ST. Analyst 2015; 140: 346
27 Cheng HP, Yang XH, Lan L, Xie LJ, Chen C, Liu C, Chu J, Li ZY, Liu L, Zhang TQ, Luo DQ, Cheng L. Angew. Chem. Int. Ed. 2020; 59: 10645
28 Gan Y, Li Y, Zhou H, Wang R. Org. Lett. 2022; 24: 6625
29 Zhou HL, Li YY, Zhang JW, Wang L, Zheng YY, Begley T, Sheng J, Wang R. bioRxiv 2022; preprint
30 Wang, S.; Zhou, H. L.; Li, Y. Y.; Zheng, Y. Y.; Sheng, J.; Wang, R. Bioorthogonal in-cell labeling and profiling of N ⁶-isopentenyladenosine (i⁶A) modified RNA, unpublished.
31 Trinkle-Mulcahy L.; F1000Res.; 2019, 8: F1000 Faculty Rev-135;
32 Roux KJ, Kim DI, Raida M, Burke B. J. Cell Biol. 2012; 196: 801
33 Hung V, Zou P, Rhee H.-Y, Udeshi ND, Cracan V, Svinkina T, Carr SA, Mootha VK, Ting AY. Mol. Cell 2014; 55: 332
34 Fields S, Song O. Nature 1989; 340: 245
35 Dobzhansky T. Genetics 1946; 31: 269
36 Zhang Y. Proteins 2009; 77: 100
37 Flor A., Pagacz J., Thompson D., Kron S.; J. Visualized Exp.; 2022, 187: e64176;
38 Mu Q, Cui K, Wang ZJ, Matsuda T, Cui W, Kato H, Namiki S, Yamazaki T, Frauenlob M, Nonoyama T, Tsuda M, Tanaka S, Nakajima T, Gong JP. Nat. Commun. 2022; 13: 6213