Citation: He Bo, Wang Dawei, Yang Wenchao, Chen Qiong, Yang Guangfu. Advances in Research on 4-Hydroxyphenylpyruvate Dioxygenase (HPPD) Structure and Pyrazole-Containing Herbicides[J]. Chinese Journal of Organic Chemistry, ;2017, 37(11): 2895-2904. doi: 10.6023/cjoc201705031 shu

Advances in Research on 4-Hydroxyphenylpyruvate Dioxygenase (HPPD) Structure and Pyrazole-Containing Herbicides

He Bo ^a ,
Wang Dawei ^b ,
Yang Wenchao ^a ,
Chen Qiong ^a ,
Yang Guangfu ^a,b,,

a.
Key Laboratory of Pesticide and Chemical Biology, College of Chemistry, Central China Normal University, Wuhan 430079
b.
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071

Corresponding author: Yang Guangfu, gfyang@mail.ccnu.edu.cn
Received Date: 21 May 2017
Revised Date: 22 June 2017
Available Online: 4 November 2017
Fund Project: Project supported by the National Key Technology Research and Development Program of the Ministry of Science and Technology (No. 2014BAD20B01), the National Natural Science Foundation of China (No. 21372093, 21672079) and the Chinese Universities Basic Scientific Research (No. CCNU15A02011)the Chinese Universities Basic Scientific Research CCNU15A02011the National Natural Science Foundation of China 21372093the National Natural Science Foundation of China 21672079the National Key Technology Research and Development Program of the Ministry of Science and Technology 2014BAD20B01

Figures(11)

4-Hydroxyphenylpyruvate dioxygenase (HPPD), a target for green herbicide discovery, has recently attracted a large number of famous scientists attention owing to controlling efficacy of resistant weeds. The structures of HPPD, inhibitors binding sites, mode of action and their metabolites are summarized. The current commercial and developing pyrazole-containing herbicides of HPPD are analyzed. Based on combining theory and practical application, a direction to find or design a new inhibitor is also oriented.
- 4-hydroxyphenylpyruvate dioxygenase,
- mode of action,
- binding site,
- herbicide
1. [1]
  Yang, G. F. Curr. Pharm. Des. 2014, 2, 0685.
2. [2]
  Hrens, H.; Lange, G.; Müller, T.; Rosinger, C.; Willms, L.; van Almsick, A. Angew. Chem., Int. Ed. 2013, 52, 9388. doi: 10.1002/anie.v52.36
3. [3]
  Beaudegnies, R.; Edmunds, A. J. F.; Fraser, T. E. M.; Hall, R. G.; Hawkes, T. R.; Mitchell, G.; Schaetzer, J.; Wendeborn, S.; Wibley, J. Bioorg. Med. Chem. 2009, 17, 4134. doi: 10.1016/j.bmc.2009.03.015
4. [4]
  Zhou, Y. Y.; Li, Z. M. World Pestic. 2013, 35, 1(in Chinese).
5. [5]
  Yin, Z. D. ; Zhang, L. ; Chen, H. ; Wang, Y. Y. ; Ouyang, G. P. Liaoning Chem. Ind. 2016, 45, 739 (in Chinese).
6. [6]
  Deng, H. X.; Qian, Y. Y.; Chen, Y. P. Zhejiang Chem. Ind. 2012, 43, 1(in Chinese).
7. [7]
  Yang, W. C.; Lin, H. Y.; Yang, S. G.; Liu, W. N.; Yang, G. F. Chin. J. Pestic. Sci. 2013, 15, 139(in Chinese).
8. [8]
  Lee, M. H.; Zhang, Z. H.; MacKinnon, C. H.; Baldwin, J. E.; Crouch, N. P. FEBS Lett. 1996, 393, 269. doi: 10.1016/0014-5793(96)00902-7
9. [9]
  Ling, T.; Shiu, S.; Yang, D. Bioorg. Med. Chem. 1999, 7, 1459. doi: 10.1016/S0968-0896(99)00062-0
10. [10]
  Ellis, M. K.; Whitfield, A. C.; Gowans, L. A.; Auton, T. R.; Provan, W. M.; Lock, E. A.; Lee, D. L.; Smith, L. L. Chem. Res. Toxicol. 1996, 9, 24. doi: 10.1021/tx950100w
11. [11]
  Endo, F.; Awata, H.; Tanoue, A.; Ishiguro, M.; Eda, Y.; Ttani, K.; Matsuda, I. J. Biol. Chem. 1992, 267, 24235.
12. [12]
  Barta, I. C.; Böger, P. Pest. Sci. 1996, 48, 109. doi: 10.1002/(SICI)1096-9063(199610)48:2<>1.0.CO;2-N
13. [13]
  Garcia, I.; Rodgers, M.; Lenne, C.; Rolland, A.; Sailland, A.; Matringe, M. Biochem. J. 1997, 325, 761. doi: 10.1042/bj3250761
14. [14]
  Yang, C.; Pflugrath, J. W.; Camper, D. L.; Foster, M. L.; Pernich, D. J.; Walsh, T. A. Biochemistry 2004, 43, 10414. doi: 10.1021/bi049323o
15. [15]
  Ruetschi, U.; Odelhog, B.; Lindstedt, S.; Barros-soderling, J.; Persson, B.; Jornvall, H. Eur. J. Biochem. 1992, 205, 463. doi: 10.1111/ejb.1992.205.issue-2
16. [16]
  Johnson-Winters, K.; Purpero, V. M.; Kavana, M.; Moran, G. R. Biochemistry 2005, 44, 7189. doi: 10.1021/bi047625k
17. [17]
  Fritze, I. M.; Linden, L.; Freigang, J.; Auerbach, G.; Huber, R.; Steinbacher, S. Plant Physiol. 2004, 134, 1388. doi: 10.1104/pp.103.034082
18. [18]
  Brownlee, J. M.; Johnson-Winters, K.; Harrison, D. H. T.; Moran, G. R. Biochemistry 2004, 43, 6370. doi: 10.1021/bi049317s
19. [19]
  Richaed, W. L.; Jane, W. B. Crit. Rev. Toxicol. 2013, 43, 185. doi: 10.3109/10408444.2013.764279
20. [20]
  Lin, J.; Li, Z. G.; Zou, J. W.; Lu, S. Y. Acta Chim. Sinica 2012, 70, 1309(in Chinese).
21. [21]
  Wójcik, A.; Broclawik, E.; Siegbahn, P. E. M.; Borowski, T. Biochemistry 2012, 51, 9570. doi: 10.1021/bi3010957
22. [22]
  Neidig, M. L.; Decker, A.; Choroba, O. W.; Huang, F.; Kavana, M.; Moran, G. R.; Spencer, J. B.; Solomon, E. I. Proc. Natl. Acad. Sci.U. S. A. 2006, 103, 12966. doi: 10.1073/pnas.0605067103
23. [23]
  Raspail, C.; Graindorge, M.; Moreau, Y.; Crouzy, S.; Lefebvre, B.; Robin, A. Y.; Dumas, R.; Matringe, M. J. Biol. Chem. 2011, 286, 26061. doi: 10.1074/jbc.M111.227595
24. [24]
  Riggins, C. W.; Peng, Y.; Stewart, C. N.; Tranel, P. J. Pest Manag. Sci. 2010, 66, 1042. doi: 10.1002/ps.2006
25. [25]
  Wójcik, A.; Broclawik, E.; Siegbahn, P. E. M.; Lundberg, M.; Moran, G.; Borowski, T. J. Am. Chem. Soc. 2014, 136, 14472. doi: 10.1021/ja506378u
26. [26]
  Lin, J. F.; Sheih, Y. L.; Chang, T. C.; Chang, N. Y.; Chang, C. W.; Shen, C. P.; Lee, H. J. PLoS One 2013, 8, e69733. doi: 10.1371/journal.pone.0069733
27. [27]
  Diebold, A. R.; Brown-Marshall, C. D.; Neidig, M. L.; Brownlee, J. M.; Moran, G. R.; Solomon, E. I. J. Am. Chem. Soc. 2011, 133, 18148. doi: 10.1021/ja202549q
28. [28]
  Wang, D. W. Ph.D. Dissertation, Central China Normal University, Wuhan, 2015 (in Chinese).
29. [29]
  Kimura, F. Jpn. Pestic. Inform. 1984, 45, 24.
30. [30]
  Rene, L.; Michael, K.; Joachim, G.; Michael, R.; Von, D. W. US 20030149276, 2003 [Chem. Abstr. 2003, 136, 118263].
31. [31]
  Schmitt, M.; van Almsick, A.; Preuss, R.; Willms, L.; Auler, T.; Bieringer, H.l; Thuerwaechter, F. WO 2001/074785, 2001 [Chem. Abstr. 2001, 135, 288780].
32. [32]
  Lian, L.; Zheng, Y. R.; He, B.; Peng, X. G.; Jin, T.; Cui, Q. CN 105218449, 2016 [Chem. Abstr. 2016, 164, 175130].
33. [33]
  Peng, X. G.; Jin, T.; Zhang, J. Y.; Zhao, D.; Cui, Q. CN 1568549, 2016 [Chem. Abstr. 2016, 165, 162543].
34. [34]
  Yamaoka, K.; Nakagawa, M.; Ishida, M. J. Pestic. Sci. 1987, 12, 209. doi: 10.1584/jpestics.12.209
35. [35]
  Wolf, J. K.; Termes, S. C. Fed. Regist. 2013, 78, 48068.
36. [36]
  Mikio, Y.; Yasumi, K.; Takashi, M.; Atsushi, N. JP 2013040141, 2013 [Chem. Abstr. 2013, 158, 381770].
37. [37]
  Wang, D. W.; Lin, H. Y.; Cao, R. J.; Chen T.; Yang, S. G.; Chen, Q.; Yang, W. C.; Yang, G. F. J. Agric. Food Chem. 2015, 63, 5587. doi: 10.1021/acs.jafc.5b01530
38. [38]
  Wang, D. W.; Lin, H. Y.; Cao, R. J.; Yang, S. G.; Chen, T.; He, B.; Chen, Q.; Yang, W. C.; Yang, G. F. Acta Chim. Sinica 2015, 73, 29(in Chinese).
39. [39]
  Xu, Y. L.; Lin, H. Y.; Cao, R. J.; Ming, Z. Z.; Yang, W. C.; Yang, G. F. Bioorg. Med. Chem. 2014, 22, 5194. doi: 10.1016/j.bmc.2014.08.011
40. [40]
  Xu, Y. L.; Lin, H. Y.; Ruan, X.; Yang, S. G.; Hao, G. F.; Yang, W. C.; Yang, G. F. Eur. J. Med. Chem. 2015, 92, 427. doi: 10.1016/j.ejmech.2015.01.018
41. [41]
  Lei, K.; Hua, X. W.; Tao, Y. Y.; Liu, Y.; Liu, N.; Ma, Y.; Li, Y. H.; Xu, X. H.; Kong, C. H. Bioorg. Med. Chem. 2016, 24, 92. doi: 10.1016/j.bmc.2015.11.032
42. [42]
  Matthias, W. Bioorg. Med. Chem. 2009, 17, 4221. doi: 10.1016/j.bmc.2008.11.006
43. [43]
  Wang, B. L.; Li, Q. N.; Zhan, Y. Z.; Xiong, L. X.; Yu, S. J.; Li, Z. M. Phosphorus Sulfur, Silicon Relat. Elem. 2014, 189, 483. doi: 10.1080/10426507.2013.829832
44. [44]
  Wang, B. L.; Wu, J.; Liu, Q. X.; Li, Y. H.; Song, H. B.; Li, Z. M. Phosphorus Sulfur, Silicon Relat. Elem. 2015, 190, 66. doi: 10.1080/10426507.2014.919503
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沈阳化工大学材料科学与工程学院沈阳 110142

Advances in Research on 4-Hydroxyphenylpyruvate Dioxygenase (HPPD) Structure and Pyrazole-Containing Herbicides

南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积

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通讯作者: 陈斌, bchen63@163.com