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
1. [1]
  Wei Shao , Wanqun Zhang , Pingping Zhu , Wanqun Hu , Qiang Zhou , Weiwei Li , Kaiping Yang , Xisheng Wang . Design and Practice of Ideological and Political Cases in the Course of Instrument Analysis Experiment: Taking the GC-MS Experiment as an Example. University Chemistry, 2024, 39(2): 147-154. doi: 10.3866/PKU.DXHX202309048
2. [2]
  Qiuting Zhang , Fan Wu , Jin Liu , Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174
3. [3]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
4. [4]
  Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052
5. [5]
  Zunxiang Zeng , Yuling Hu , Yufei Hu , Hua Xiao . Analysis of Plant Essential Oils by Supercritical CO₂Extraction with Gas Chromatography-Mass Spectrometry: An Instrumental Analysis Comprehensive Experiment Teaching Reform. University Chemistry, 2024, 39(3): 274-282. doi: 10.3866/PKU.DXHX202309069
6. [6]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
7. [7]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
8. [8]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
9. [9]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
10. [10]
  Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
11. [11]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
12. [12]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
13. [13]
  Zian Lin , Yingxue Jin . Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry (MALDI-MS) for Disease Marker Screening and Identification: A Comprehensive Experiment Teaching Reform in Instrumental Analysis. University Chemistry, 2024, 39(11): 327-334. doi: 10.12461/PKU.DXHX202403066
14. [14]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
15. [15]
  Houjin Li , Lin Wu , Xingwen Sun , Yuan Zheng , Zhanxiang Liu , Shuanglian Cai , Ying Xiong , Guangao Yu , Qingwen Liu , Jie Han , Xin Du , Chengshan Yuan , Qihan Zhang , Jianrong Zhang , Shuyong Zhang . Basic Operations and Specification Suggestions for Organic Chemical Chromatography Experiments. University Chemistry, 2025, 40(5): 93-105. doi: 10.12461/PKU.DXHX202408100
16. [16]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
17. [17]
  Wenliang Wang , Weina Wang , Lixia Feng , Nan Wei , Sufan Wang , Tian Sheng , Tao Zhou . Proof and Interpretation of Severe Spectroscopic Selection Rules. University Chemistry, 2025, 40(3): 415-424. doi: 10.12461/PKU.DXHX202408063
18. [18]
  Jingming Li , Bowen Ding , Nan Li , Nurgul . Application of Comparative Teaching Method in Experimental Project Design of Instrumental Analysis Course: A Case Study in Chromatography Experiment Teaching. University Chemistry, 2024, 39(8): 263-269. doi: 10.3866/PKU.DXHX202312078
19. [19]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
20. [20]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1127)
HTML views(176)

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