Citation: Liu Guijun, Shi Hao. Progress in Chiral Recognition Based on Molecular Tweezers[J]. Chinese Journal of Organic Chemistry, ;2016, 36(11): 2583-2601. doi: 10.6023/cjoc201603037 shu

Progress in Chiral Recognition Based on Molecular Tweezers

Liu Guijun ,
Shi Hao ^*,,

1.
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014

Corresponding author: Shi Hao, shihao@zjut.edu.cn
Received Date: 23 March 2016
Revised Date: 19 June 2016

Fund Project: the Natural Science Foundation of Zhejiang Province LY13B020013

Figures(48)

Chirality is a common phenomenon in nature. Designing and synthesis of novel artificial receptors to emulate the molecular recognition in living organism has become the challenging forefront of bioorganic chemistry and supramolecular chemistry. Molecular tweezers have been widely applied in chiral molecular recognition and detection for its easily modified structure. Molecular tweezers and their chiral recognition properties detected by spectrometry, chromatography and mass spectrometry are summarized in this paper, and the prospect of molecular tweezers is also discussed.
- molecular tweezers artificial receptor,
- chiral recognition,
- spectrometry,
- chromatography,
- mass spectrometry
1. [1]
  Berthod, A. Anal. Chem. 2006, 78, 2093. doi: 10.1021/ac0693823
2. [2]
  Qin, H. J.; Yang, X.; He, Y. B.; Qin, Y. G.; Liu, G. J. Acta Chim. Sinica 2006, 64, 2271 (in Chinese).
3. [3]
  Qing, G. Y.; Liu, S. Y.; He, Y. B. Prog. Chem. 2008, 20, 1933 (in Chinese).
4. [4]
  Berthod, A. Anal. Chem. 2006, 78, 2093. doi: 10.1021/ac0693823
5. [5]
  Rebek, J. Acc. Chem. Res. 1990, 23, 399. doi: 10.1021/ar00180a001
6. [6]
  Jo, H. H.; Lin, C. Y.; Anslyn, E. V. Acc. Chem. Res. 2014, 47, 2212. doi: 10.1021/ar500147x
7. [7]
  Seifert, H. M.; Jiang, Y. B.; Anslyn, E. V. Chem. Commun. 2014, 50, 15330. doi: 10.1039/C4CC07927B
8. [8]
  Chen, Y. Z.; Li, H.; Yang, H. J.; Hua, S. M.; Li, H. Q.; Zhao, F. Z.; Chen, N. Y. Org. Mass Spectrom. 1988, 23, 821. doi: 10.1002/(ISSN)1096-9888
9. [9]
  Sawada, M. Mass Spectrom. Rev. 1997, 16, 73. doi: 10.1002/(ISSN)1098-2787
10. [10]
  Quinn, T. P.; Atwood, P. D.; Tanski, J. M.; Moore, T. F.; Folmer-Anderson, J. F. J. Org. Chem. 2011, 76, 10020. doi: 10.1021/jo2018203
11. [11]
  Wenzel, T. J.; Amonoo, E. P.; Shariff, S. S.; Aniagyei, S. E. Tetrahedron:Asymmetry 2003, 14, 3099. doi: 10.1016/j.tetasy.2003.07.019
12. [12]
  Seker, S.; Baris, D.; Arslan, N.; Turgut, Y.; Pirinççioglu, N.; Togrul, M. Tetrahedron:Asymmetry 2014, 25, 411. doi: 10.1016/j.tetasy.2014.01.009
13. [13]
  Nandipati, V.; Akinapelli, K.; Koya, L.; Starnes, S. D. Tetrahe-dron Lett. 2014, 55, 985. doi: 10.1016/j.tetlet.2013.12.046
14. [14]
  Yang, K.; Li, S. Z.; Wang, Y. H.; Zhang, W. Z.; Xu, Z. H.; Zhou, X. Y.; Zhu, R. X.; Luo, J.; Wan, Q. RSC Adv. 2014, 4, 6517. doi: 10.1039/c3ra46723f
15. [15]
  Garcia-Tellado, F.; Albert, J.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1991, 1761.
16. [16]
  Goswami, S.; Ghosh, K.; Dasgupta, S. J. Org. Chem. 2000, 65, 1907. doi: 10.1021/jo9909204
17. [17]
  Liu, S. Y.; Lei, F.; He, Y. B.; Chan, W. H.; Yeung, K. T.; Cheng, Y. K.; Yang, R-H. Org. Lett. 2005, 7, 5825. doi: 10.1021/ol052341t
18. [18]
  Li, S. Y.; Zheng, Q. Y.; Chen, C. F.; Huang, Z. T. Tetrahedron:Asymmetry 2005, 16, 2816. doi: 10.1016/j.tetasy.2005.07.013
19. [19]
  Qing, G. Y.; He, Y. B.; Wang, F.; Qin, H. J.; Hu, C. G.; Yang, X. Eur. J. Org. Chem. 2007, 11, 1768.
20. [20]
  Qing, G. Y.; Qin, H. J.; He, Y. B.; Hu, C. G.; Wang, F.; Hu, L. Supramol. Chem. 2008, 20, 265. doi: 10.1080/10610270701200180
21. [21]
  Feng, Z. Q. M.S. Thesis, Suzhou University, Suzhou, 2012 (in Chinene).
22. [22]
  Jiang, J. X. Ph.D. Dissertation, Suzhou University, Suzhou, 2013 (in Chinese).
23. [23]
  Granda, J. M.; Jurczak, J. Org. Lett. 2013, 15, 4730. doi: 10.1021/ol402074u
24. [24]
  Granda, J. M.; Jurczak, J. Chem. Eur. J. 2014, 20, 12368. doi: 10.1002/chem.v20.39
25. [25]
  Granda, J. M.; Jurczak, J. Chem. Eur. J. 2015, 21, 16585. doi: 10.1002/chem.v21.46
26. [26]
  Li, Z. Y.; Zhou, K.; Lai, Y.; Sun, X. Q.; Wang, L. Y. Chin. J. Org. Chem. 2015, 35, 1531 (in Chinese). doi: 10.6023/cjoc201502018
27. [27]
  Gao, G.; Lv, C.; Li, Q.; Ai, L.; Zhang, J. Tetrahedron Lett. 2015, 56, 6742. doi: 10.1016/j.tetlet.2015.10.060
28. [28]
  González-Mendoza, L.; Escorihuela, J. Altava, B.; Burguete, M. I.; Luis, S. V. Org. Biomol. Chem. 2015, 13, 5450. doi: 10.1039/C5OB00348B
29. [29]
  Feng, H. T.; Zhang, X.; Zheng, Y. S. J. Org. Chem. 2015, 80, 8096. doi: 10.1021/acs.joc.5b01194
30. [30]
  Wen, K.; Yu, S.; Huang, Z.; Chen, L.; Xiao, M.; Yu, X.; Pu, L. J. Am. Chem. Soc. 2015, 137, 4517. doi: 10.1021/jacs.5b01049
31. [31]
  Fuentes, A. L.; Herrero, A, G.; Rubio, O. H.; Monleon, L. M.; Rubio, L, S.; Alcazar, V.; Sanz, F.; Moran, J. R. Org. Biomol. Chem. 2015, 13, 493. doi: 10.1039/C4OB01954G
32. [32]
  Botha, F.; Budka, J.; Eigner, V.; Hudecek, O.; Vrzal, L.; Cisarova, I.; Lhotak, P. Tetrahedron 2014, 70, 477. doi: 10.1016/j.tet.2013.11.030
33. [33]
  Mackova, M.; Miksatko, J.; Budka, J.; Eigner, V.; Curinova, p.; Lhotak, P. New J. Chem. 2015, 39, 1382. doi: 10.1039/C4NJ01956C
34. [34]
  Lammerhofer, M.; Svec, F.; Frechet, J. M. J.; Lindner, W. TrAC, Trends Anal. Chem. 2000, 19, 676. doi: 10.1016/S0165-9936(00)00049-2
35. [35]
  Wang, W. Y. M.S. Thesis, Shanxi University, Taiyuan, 2009 (in Chinese).
36. [36]
  Hernfindez, J. V.; Almaraz, M.; Raposo, C.; Martin, M.; Lithgow, A.; Crego, M.; Caballero, C.; Moran, J. R. Tetrahedron Lett. 1998, 39, 7401. doi: 10.1016/S0040-4039(98)01606-2
37. [37]
  Martin, M.; Raposo, C.; Oliva, A. L.; Simon, L.; Caballlero, C.; Moran, J. Chem. Lett. 2000, 0, 718.
38. [38]
  Gazic, I.; Kontrec, D.; Lesac, A.; Vinkovic, V. Tetrahedron:Asymmetry 2005, 16, 1175. doi: 10.1016/j.tetasy.2005.01.042
39. [39]
  Choi, H. J.; Ha, H. J.; Shin, M. S.; Jin, J. S.; Hyun, M. H. J. Liq. Chromatogr. Related Technol. 2009, 32, 1879. doi: 10.1080/10826070903091589
40. [40]
  Yu, H.; Yin, C.; Jia, C.; Jin, Y.; Ke, Y.; Liang, X. Chirality 2012, 24, 391. doi: 10.1002/chir.v24.5
41. [41]
  Wu, J.; Su, P.; Guo, D.; Huang, J.; Yang, Y. New J. Chem. 2014, 38, 3630. doi: 10.1039/C4NJ00030G
42. [42]
  Zhou, J.; Wang, Y.; Liu, Y.; Tang, J.; Tang, W. Anal. Chim. Acta 2015, 868, 73. doi: 10.1016/j.aca.2015.02.013
43. [43]
  Wernisch, S.; Pell, R.; Lindner, W. J. Sep. Sci. 2012, 35(13), 155.
44. [44]
  Hyum, M. H.; Jin, J, S.; Lee, W. J. Chromatogr. A 1998, 822, 391.
45. [45]
  Lu, Z.; Wu, P.; Zi, M.; Yang, C.; Kong, J.; Yuan, L. Chin. J. Org. Chem. 2015, 35, 217. doi: 10.6023/cjoc201408011
46. [46]
  Wang, D.; Zhao, J.; Wu, H.; Wu, H.; Cai, J.; Ke, Y.; Liang, X. J. Sep. Sci. 2015, 38, 205. doi: 10.1002/jssc.201400977
47. [47]
  Schug, K. A.; Lindner, W. J. Sep. Sci. 2005, 28, 1932. doi: 10.1002/(ISSN)1615-9314
48. [48]
  Ranc, V.; Havlicek, V.; Bednar, P.; Lemr, K. Eur. J. Mass Spec-trom. 2008, 14, 411. doi: 10.1255/ejms.978
49. [49]
  Chen, Y.; Li, H.; Yang, H.; Hua, S.; Li, H.; Zhao, F.; Chen, N. Org. Mass Spectrom. 1988, 23, 821. doi: 10.1002/(ISSN)1096-9888
50. [50]
  Sawada, M.; Okumura, Y.; Shizuma, M.; Takai, Y.; Hidaka, Y.; Yamada, H.; Tanaka, T.; Kaneda, T.; Hirose, K. J. Am. Chem. Soc. 1993, 115, 7381. doi: 10.1021/ja00069a041
51. [51]
  Sawada, M.; Takai, Y.; Yamada, H.; Hirayama, S.; Kaneda, T.; Tanaka, T.; Kamada, K.; Mizooku, T.; Takeuchi, S.; Ueno, K.; Hirose, K.; Tobe, Y.; Naemura, K. J. Am. Chem. Soc. 1995, 117, 7726. doi: 10.1021/ja00134a017
52. [52]
  Liu, Q.; Zhang, S.; Wu, B.; Guo, J.; Xie, J.; Gu, M.; Zhao, Y.; Yun, L.; Liu, K. Anal. Chem. 2005, 77, 5302. doi: 10.1021/ac050318f
53. [53]
  Shizuma, M.; Adachi, H.; Ono, D.; Sato, H.; Nakamura, M. Chirality 2009, 21, 324. doi: 10.1002/chir.v21:2
54. [54]
  Zu, C. L.; Woolfolk, J, A.; Koscho, M. E. Anal. Chim. Acta 2010, 661, 60. doi: 10.1016/j.aca.2009.12.011
55. [55]
  Zuo, A. P. M.S. Thesis, Central China Normal University, Wuhan, 2013 (in Chinese).
56. [56]
  Fayzullin, R. R.; Bredikhina, Z. A.; Sharafutdinova, D. R.; Bazanova, O. B.; Bredikhin, A. A. Russ. J. Org. Chem. 2014, 50, 611. doi: 10.1134/S1070428014040319
57. [57]
  Bredikhina, Z. A.; Sharafutdinova, D. R.; Bazanova, O. B.; Ba-baev, V. M.; Fayzullin, R. R.; Rizvanov, I. K.; Bredikhin, A. A. J. Incl. Phenom. Macrocycl. Chem. 2014, 80, 417. doi: 10.1007/s10847-014-0430-6
58. [58]
  Alexander, J. M.; Clark, J. L.; Brett, T. J.; Stezowski, J. J. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 5115. doi: 10.1073/pnas.072647599
59. [59]
  Nunez-Aguero, C. J.; Escobar-Llanos, C. M.; Diaz, D.; Jaime, C.; Garduno-Juarez, R. Tetrahedron 2006, 62, 4162. doi: 10.1016/j.tet.2006.02.010
60. [60]
  Zhao, C.; Cann, N. M. J. Chromatogr. A 2007, 1149, 197. doi: 10.1016/j.chroma.2007.03.073
61. [61]
  Yang, Z. Y.; Liu, L.; Cheng, Y.; Wang, Y. L.; Chen, S. H.; Gan, Y.; Lv, D. J. Sichuan Univ. (Nat. Sci. Ed. 2000, 37, 477 (in Chinese).
62. [62]
  Yang, Z. Y.; Zhang, W. H. Chem. Res. Appl. 2008, 20, 386 (in Chinese).
63. [63]
  Liu, F.; Lu, G. Y.; He, W. J.; Liu, M. H.; Zhu, L. G. Thin Solid Films 2004, 468, 244. doi: 10.1016/j.tsf.2004.03.047
64. [64]
  Tu, T.; Fang, W.; Bao, X.; Li, X.; Dotz, K. H. Angew. Chem., Int. Ed. 2011, 50, 6601. doi: 10.1002/anie.v50.29
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