Citation: Zhang Ruipu, Luo Sanzhong. Bio-inspired quinone catalysis[J]. Chinese Chemical Letters, ;2018, 29(8): 1193-1200. doi: 10.1016/j.cclet.2018.02.009 shu

Bio-inspired quinone catalysis

Zhang Ruipu ^a,b ,
Luo Sanzhong ^a,b,,

a.
Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: Luo Sanzhong, luosz@iccas.ac.cn
Received Date: 3 January 2018
Revised Date: 31 January 2018
Accepted Date: 14 February 2018
Available Online: 21 August 2018

Figures(30)

Quinoproteins are an important type of redox enzymes for biological oxidation processes. Inspired by the quinone cofactors, particularly from copper amine oxidases, a number of small molecular quinone catalysts have been developed for C-H functionalizations of amines. Bio-inspired quinone catalysts have significantly expanded the substrate scope to include branched primary amines, secondary amines and tertiary amines, far beyond the scope of quinoproteins. This review summarizes the evolution of quinone catalysts, their mechanism and catalytic applications.
- ortho-Quinone catalysis,
- Amine oxidation,
- Organocatalysis,
- Bio-inspired,
- C-H functionalization
1. [1]
  (a) C. Anthony, Biochem. J. 320 (1996) 697-711;
  (b) K. Matsushita, H. Toyama, M. Yamada, O. Adachi, Appl. Microbiol. Biotechnol. 58 (2002) 13-22.
2. [2]
  (a) J. G. Hauge, J. Biol. Chem. 239 (1964) 3630-3639;
  (b) C. Anthony, L. J. Zatman, Biochem. J. 104 (1967) 960-969;
  (c) S. A. Salisbury, H. S. Forrest, W. B. T. Cruse, O. Kennard, Nature 280 (1979) 843-844;
  (d) J. A. Duine, J. Frank, Biochem. J. 187 (1980) 221-226;
  (e) C. Anthony, Arch. Biochem. Biophys. 428 (2004) 2-9;
  (f) H. Toyama, F. S. Mathews, O. Adachi, K. Matsushita, Arch. Biochem. Biophys. 428 (2004) 10-21.
3. [3]
  S. Janes, D. Mu, D. Wemmer, et al., Science 248(1990) 981-987. doi: 10.1126/science.2111581
4. [4]
  S.X. Wang, M. Mure, K.F. Medzihradszky, et al., Science 273(1996) 1078-1084. doi: 10.1126/science.273.5278.1078
5. [5]
  W. McIntire, D. Wemmer, A. Chistoserdov, M. Lidstrom, Science 252(1991) 817-824. doi: 10.1126/science.2028257
6. [6]
  A. Satoh, J.K. Kim, I. Miyahara, et al., J. Biol. Chem. 277(2002) 2830-2834. doi: 10.1074/jbc.M109090200
7. [7]
  V.J. Klema, C.M. Wilmot, Int. J. Mol. Sci. 13(2012) 5375-5405. doi: 10.3390/ijms13055375
8. [8]
  J.P. Van Dijken, P. Bos, Arch. Microbiol. 128(1981) 320-324. doi: 10.1007/BF00422538
9. [9]
  M. Mure, S.A. Mills, J.P. Klinman, Biochem 41(2002) 9269-9278. doi: 10.1021/bi020246b
10. [10]
  (a) C. Hartmann, J. P. Klinman, Biochem 30 (2002) 4605-4611;
  (b) S. M. Janes, J. P. Klinman, Biochem 30 (2002) 4599-4605;
  (c) S. M. Janes, M. M. Palcic, C. H. Scaman, et al., Biochem 31 (1992) 12147-12154;
  (d) C. Hartmann, P. Brzovic, J. P. Klinman, Biochem 32 (1993) 2234-2241;
  (e) M. Mure, J. P. Klinman, Synth. J. Am. Chem. Soc. 115 (1993) 7117-7127;
  (f) M. Mure, J. P. Klinman, J. Am. Chem. Soc. 117 (1995) 8698-8706;
  (g) M. Mure, J. P. Klinman, J. Am. Chem. Soc. 117 (1995) 8707-8718;
  (h) J. Plastino, E. L. Green, J. Sanders-Loehr, J. P. Klinman, Biochem 38 (1999) 8204-8216;
  (i) M. Mure, S. X. Wang, J. P. Klinman, J. Am. Chem. Soc. 125 (2003) 6113-6125.
11. [11]
  (a) Y. Lee, L. M. Sayre, J. Am. Chem. Soc. 117 (1995) 11823-11828;
  (b) Y. Lee, L. M. Sayre, J. Am. Chem. Soc. 117 (1995) 3096-3105;
  (c) Y. Lee, H. B. Jeon, H. Huang, L. M. Sayre, J. Org. Chem. 66 (2001) 1925-1937.
12. [12]
  Y. Murakami, N. Yoshimoto, N. Fujieda, et al., J. Org. Chem. 72(2007) 3369-3380. doi: 10.1021/jo0700272
13. [13]
  Y. Zhang, C. Ran, G. Zhou, L.M. Sayre, Bioorg. Med. Chem. 15(2007) 1868-1877. doi: 10.1016/j.bmc.2006.11.025
14. [14]
  (a) A. E. Wendlandt, S. S. Stahl, Angew. Chem. Int. Ed. 54 (2015) 14638-14658;
  (b) X. Lu, B. Xiao, R. Shang, L. Liu, Chin. Chem. Lett. 27 (2016) 305-311;
  (c) M. Largeron, Org. Biomol. Chem. 15 (2017) 4722-4730.
15. [15]
  M. Largeron, M.B. Fleury, J. Org. Chem. 65(2000) 8874-8881. doi: 10.1021/jo000478l
16. [16]
  A.E. Wendlandt, S.S. Stahl, Org. Lett. 14(2012) 2850-2853. doi: 10.1021/ol301095j
17. [17]
  A.E. Wendlandt, S.S. Stahl, J. Am. Chem. Soc. 136(2014) 506-512. doi: 10.1021/ja411692v
18. [18]
  H. Yuan, W.J. Yoo, H. Miyamura, S. Kobayashi, J. Am. Chem. Soc. 134(2012) 13970-13973. doi: 10.1021/ja306934b
19. [19]
  Y. Qin, L. Zhang, J. Lv, S. Luo, J.P. Cheng, Org. Lett. 17(2015) 1469-1472. doi: 10.1021/acs.orglett.5b00351
20. [20]
  Y. Goriya, H.Y. Kim, K. Oh, Org. Lett. 18(2016) 5174-5177. doi: 10.1021/acs.orglett.6b02697
21. [21]
  R. Zhang, Y. Qin, L. Zhang, S. Luo, in revision.
22. [22]
  M. Largeron, A. Neudorffer, M.B. Fleury, Angew. Chem. Int. Ed. 42(2003) 1026-1029. doi: 10.1002/anie.200390263
23. [23]
  (a) E. Blattes, M. B. Fleury, M. Largeron, J. Org. Chem. 69 (2004) 882-890;
  (b) M. Largeron, A. Neudorffer, M. Vuilhorgne, E. Blattes, M. B. Fleury, Angew. Chem. Int. Ed. 41 (2002) 824-827;
  (c) D. Xu, A. Chiaroni, M. Largeron, Org. Lett. 7 (2005) 5273-5276;
  (d) D. Xu, A. Chiaroni, M. B. Fleury, M. Largeron, J. Org. Chem. 71 (2006) 6374-6381;
  (e) M. Largeron, Electrochim. Acta 54 (2009) 5109-5115.
24. [24]
  M. Largeron, A. Chiaroni, M.B. Fleury, Chem. -Eur. J. 14(2008) 996-1003. doi: 10.1002/(ISSN)1521-3765
25. [25]
  M. Largeron, M.B. Fleury, Angew. Chem. Int. Ed. 51(2012) 5409-5412. doi: 10.1002/anie.201200587
26. [26]
  M. Largeron, M.B. Fleury, Chem. -Eur. J. 21(2015) 3815-3820. doi: 10.1002/chem.v21.9
27. [27]
  M. Largeron, M.B. Fleury, Chem. -Eur. J. 23(2017) 6763-6767. doi: 10.1002/chem.201701402
28. [28]
  M. Largeron, M.B. Fleury, Org. Lett. 11(2009) 883-886. doi: 10.1021/ol802885b
29. [29]
  D.V. Jawale, E. Gravel, E. Villemin, et al., Chem. Commun. 50(2014) 15251-15254. doi: 10.1039/C4CC07951E
30. [30]
  A.E. Wendlandt, S.S. Stahl, J. Am. Chem. Soc. 136(2014) 11910-11913. doi: 10.1021/ja506546w
31. [31]
  D.V. Jawale, E. Gravel, N. Shah, et al., Chem. -Eur. J. 21(2015) 7039-7042. doi: 10.1002/chem.201500148
32. [32]
  (a) K. M. Nguyen, M. Largeron, Chem. -Eur. J. 21 (2015) 12606-12610;
  (b) K. M. H. Nguyen, M. Largeron, Catal. Eur. J. Org. Chem. 2016 (2016) 1025-1032.
33. [33]
  R. Zhang, Y. Qin, L. Zhang, S. Luo, Org. Lett. 19(2017) 5629-5632. doi: 10.1021/acs.orglett.7b02786
1. [1]
  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
2. [2]
  Wenling Yuan , Fengli Li , Zhe Chen , Qiaoxin Xu , Zhenhua Guan , Nanyu Yao , Zhengxi Hu , Junjun Liu , Yuan Zhou , Ying Ye , Yonghui Zhang . AbnI: An α-ketoglutarate-dependent dioxygenase involved in brassicicene CH functionalization and ring system rearrangement. Chinese Chemical Letters, 2024, 35(5): 108788-. doi: 10.1016/j.cclet.2023.108788
3. [3]
  Si-Hua Liu , Jun-Hao Zhou , Jian-Ke Sun . Interconnecting zero-dimensional porous organic cages into sub-8 nm nanofilm for bio-inspired separation. Chinese Journal of Structural Chemistry, 2024, 43(7): 100312-100312. doi: 10.1016/j.cjsc.2024.100312
4. [4]
  Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
5. [5]
  Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp³)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
6. [6]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
7. [7]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
8. [8]
  Gang Hu , Chun Wang , Qinqin Wang , Mingyuan Zhu , Lihua Kang . The controlled oxidation states of the H₄PMo₁₁VO₄₀ catalyst induced by plasma for the selective oxidation of methacrolein. Chinese Chemical Letters, 2025, 36(2): 110298-. doi: 10.1016/j.cclet.2024.110298
9. [9]
  Jian Han , Li-Li Zeng , Qin-Yu Fei , Yan-Xiang Ge , Rong-Hui Huang , Fen-Er Chen . Recent advances in remote C(sp³)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction. Chinese Chemical Letters, 2024, 35(11): 109647-. doi: 10.1016/j.cclet.2024.109647
10. [10]
  Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
11. [11]
  Bicheng Zhu , Jingsan Xu . S-scheme heterojunction photocatalyst for H2 evolution coupled with organic oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100327-100327. doi: 10.1016/j.cjsc.2024.100327
12. [12]
  Liang Ma , Zhou Li , Zhiqiang Jiang , Xiaofeng Wu , Shixin Chang , Sónia A. C. Carabineiro , Kangle Lv . Effect of precursors on the structure and photocatalytic performance of g-C3N4 for NO oxidation and CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100416-100416. doi: 10.1016/j.cjsc.2024.100416
13. [13]
  Jian Yang , Guang Yang , Zhijie Chen . Capturing carbon dioxide from air by using amine-functionalized metal-organic frameworks. Chinese Journal of Structural Chemistry, 2024, 43(5): 100267-100267. doi: 10.1016/j.cjsc.2024.100267
14. [14]
  Huixin Chen , Chen Zhao , Hongjun Yue , Guiming Zhong , Xiang Han , Liang Yin , Ding Chen . Unraveling the reaction mechanism of high reversible capacity CuP₂/C anode with native oxidation PO_x component for sodium-ion batteries. Chinese Chemical Letters, 2025, 36(1): 109650-. doi: 10.1016/j.cclet.2024.109650
15. [15]
  Hui Li , Yanxing Qi , Jia Chen , Juanjuan Wang , Min Yang , Hongdeng Qiu . Synthesis of amine-pillar[5]arene porous adsorbent for adsorption of CO₂ and selectivity over N₂ and CH₄. Chinese Chemical Letters, 2024, 35(11): 109659-. doi: 10.1016/j.cclet.2024.109659
16. [16]
  Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
17. [17]
  Peng Wang , Jianjun Wang , Ni Song , Xin Zhou , Ming Li . Radical dehydroxymethylative fluorination of aliphatic primary alcohols and diverse functionalization of α-fluoroimides via BF₃·OEt₂-catalyzed C‒F bond activation. Chinese Chemical Letters, 2025, 36(1): 109748-. doi: 10.1016/j.cclet.2024.109748
18. [18]
  Jingping Hu , Jing Xu . Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C₁₄–epi-deoxycalyciphylline H. Chinese Chemical Letters, 2024, 35(4): 108733-. doi: 10.1016/j.cclet.2023.108733
19. [19]
  Yujia Shi , Yan Qiao , Pengfei Xie , Miaomiao Tian , Xingwei Li , Junbiao Chang , Bingxian Liu . Rhodium-catalyzed enantioselective in situ C(sp³)−H heteroarylation by a desymmetrization approach. Chinese Chemical Letters, 2024, 35(10): 109544-. doi: 10.1016/j.cclet.2024.109544
20. [20]
  Jinpeng Du , Junlin Chen , Yulong Shan , Tongliang Zhang , Yu Sun , Zhongqi Liu , Xiaoyan Shi , Wenpo Shan , Yunbo Yu , Hong He . Insight into the effects of C₃H₆ on fresh and hydrothermally aged Cu-SSZ-39 catalysts. Chinese Chemical Letters, 2025, 36(3): 110019-. doi: 10.1016/j.cclet.2024.110019

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(712)
HTML views(8)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142