Citation: Bai Dong, Zhou Yang, Lu Jihong, Liu Qingyun, Chen Qing, Tao Zhu, Xiao Xin. Study of the Interaction between Two Kinds of Cucurbit [7]urils and 3-(2-Naphthyl)-alanine[J]. Chinese Journal of Organic Chemistry, ;2018, 38(6): 1477-1483. doi: 10.6023/cjoc201801020 shu

Study of the Interaction between Two Kinds of Cucurbit [7]urils and 3-(2-Naphthyl)-alanine

Bai Dong ^a ,
Zhou Yang ^b ,
Lu Jihong ^a ,
Liu Qingyun ^c ,
Chen Qing ^a,, ,
Tao Zhu ^a ,
Xiao Xin ^a,,

a.
Key Laboratory of Macrocyclic and Supramolecular Chenmistry of Guizhou Province, Guizhou University, Guiyang 550025
b.
College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014
c.
College of Chemistry and Environmental Engineering, Shandong University of Science and Technology, Qingdao 266590

Corresponding author: Chen Qing, Xiao Xin, gyhxxiaoxin@163.com
Received Date: 13 January 2018
Revised Date: 8 February 2018
Available Online: 11 June 2018
Fund Project: the Major Program for Creative Research Groups of Guizhou Provincial Education Department 2017-028the National Natural Science Foundation of China 21561007the Science and Technology Fund of Guizhou Province 2016-1030the Innovation Program for High-Level Talents of Guizhou Province 2016-5657Project supported by the National Natural Science Foundation of China (No. 21561007), the Science and Technology Fund of Guizhou Province (No. 2016-1030), the Innovation Program for High-Level Talents of Guizhou Province (No. 2016-5657) and the Major Program for Creative Research Groups of Guizhou Provincial Education Department (No. 2017-028)

Figures(6)

The interaction of a pair of amino acid enantiomers, L-3-(2-naphthyl)-alanine (L-NA) and D-3-(2-naphthyl)-alanine (D-NA), with cucurbit[7]uril (Q[7]) and inverted cucurbit[7]uril (iQ[7]) was investigated, respectively, by using NMR spectroscopy, electronic absorption spectroscopy, fluorescence spectroscopies, isothermal titration calorimetry (ITC) experiments and MALDI-TOF mass spectrometry. Furthermore, the similarities and differences of the self-assembly patterns between the two kinds of cucurbituril with different cavity sizes and this pair of amino acid enantiomers were also researched. The results obtained from the experiment revealed that the naphthyl groups of amino acids were all entrapped in the cavity of the Q[n]s, whereas the other section of amino acids remained outside the portal and thus resulted in a more stable supramolecular self-assembly at a 1:1 ratio. Meanwhile, we found that the two different kinds of cucurbit[7]urils showed a slightly different selectivity for the L/D-NA chiral enantiomer.
- inverted cucurbit[7]uril,
- cucurbit[7]uril,
- enantiomer,
- amino acid,
- self-assembly
1. [1]
  Peczuh, M. W.; Hamilton, A. D. Chem.Rev. 2000, 100, 2479. doi: 10.1021/cr9900026
2. [2]
  Yin, H.; Hamilton, A. D. Angew.Chem., Int.Ed. 2005, 44, 4130. doi: 10.1002/(ISSN)1521-3773
3. [3]
  Schmuck, C. Coord.Chem.Rev. 2006, 250, 3053. doi: 10.1016/j.ccr.2006.04.001
4. [4]
  Urbach, A. R.; Ramalingam, V. Isr.J.Chem. 2011, 55, 664.
5. [5]
  Zhang, W.; Xu, N. W.; Yao, Z. J.; Li, K.; Zhu, Y.; Chen, L. Y.; Ye, W. L.; Deng, W. Chin.J.Org.Chem. 2016, 36, 2039(in Chinese).
6. [6]
  Freeman, W. A.; Mock, W. L.; Shih, N. Y. J.Am.Chem.Soc. 1981, 103, 7367. doi: 10.1021/ja00414a070
7. [7]
  Ni, X. L.; Xiao, X.; Cong, H.; Liang, L. L.; Chen, K.; Cheng, X. J.; Ji, N. N.; Zhu, Q. J.; Xue, S. F.; Tao, Z. Chem.Soc.Rev. 2013, 42, 9480. doi: 10.1039/c3cs60261c
8. [8]
  Yi, J. M.; Chen, M. H.; Xue, S. F.; Tao, Z. Chin.J.Org.Chem. 2016, 36, 653(in Chinese).
9. [9]
  Yin, Z. J.; Wu, Z. Q.; Lin, F.; Qi, Q. Y.; Xu, X. N.; Zhao, X. Chin.Chem.Lett. 2017, 28, 1167. doi: 10.1016/j.cclet.2017.03.029
10. [10]
  Zhang, M.; Gao, J.; Cai, M.; Jiang, J.; Tian, Z. Sci.China, Ser.B:Chem. 2016, 59, 848. doi: 10.1007/s11426-015-0535-0
11. [11]
  Day, A. I.; Blanch, R. J.; Arnold, A. P.; Lorenzo, S.; Lewis, G. R.; Dance, I. A. Angew.Chem., Int.Ed. 2002, 41, 285.
12. [12]
  Xiao, X.; Liu, J. X.; Fan, Z. F.; Chen, K.; Zhu, Q. J.; Xue, S. F.; Tao Z. Chem.Commun. 2010, 46, 3741. doi: 10.1039/b927592d
13. [13]
  Yi, J. M.; Xiao, X.; Zhang, Y. Q.; Xue, S. F.; Tao, Z.; Zhang, J. X. Acta Chim.Sinica 2014, 72, 949(in Chinese). doi: 10.7503/cjcu20131020
14. [14]
  Cui, X. W.; Chen, S. Y.; Wang, C. Z.; Zhao, W. X.; Sun, T.; Ni, X. L.; Zhang, Y. Q.; Tao, Z. Chin.Chem.Lett. 2016, 27, 173. doi: 10.1016/j.cclet.2015.10.007
15. [15]
  Ni, X. L.; Xiao, X.; Cong, H.; Zhu, Q. J.; Xue, S. F.; Tao, Z. Acc.Chem.Res. 2010, 47, 1386.
16. [16]
  Kaifer, A. E. Acc.Chem.Res. 2014, 47, 2160. doi: 10.1021/ar5001204
17. [17]
  Bai, D.; Wang, X.; Gao, Z. Z.; Qiu, S. C.; Tao, Z.; Zhang, J. X.; Xiao, X. Chin.J.Org.Chem. 2017, 37, 2022(in Chinese).
18. [18]
  Dong, N.; Wang, X. L.; Pan, J. P.; Tao, Z. Acta Chim.Sinica 2011, 69, 1431(in Chinese). doi: 10.3866/PKU.WHXB20110634
19. [19]
  Liu, Q. Y.; Chen, P. P.; Xu, Z.; Chen, M. M.; Ding, Y. N.; Yue, K.; Xu, J. Sens. Actuators, B 2017, 251, 339. doi: 10.1016/j.snb.2017.05.069
20. [20]
  Liu, Q. Y.; Ge, S. S.; Cui, G. W. Acta Crystallogr. 2009, 65, 359.
21. [21]
  Li, B.; Li, X.; Sun, X.; Wang, N. Chin. J. Chem. 2016, 34, 1114. doi: 10.1002/cjoc.v34.11
22. [22]
  Li, T. T.; Wen, L. L.; Ji, H. L.; Liu, F. Y.; Sun, S. G. Chin.Chem.Lett. 2017, 28, 463. doi: 10.1016/j.cclet.2016.10.004
23. [23]
  Freeman, W. A.; Mock, W. L.; Shih, N. Y. J.Am.Chem.Soc. 1981, 103, 7367. doi: 10.1021/ja00414a070
24. [24]
  Zhao, Y. J.; Xue, S. F.; Zhu, Q. J.; Tao, Z.; Zhang, J. X.; Wei, Z. B.; Long, L. S.; Hu, M. L.; Xiao, H. P.; Day, A. I. Chin.Sci.Bull. 2004, 49, 1111. doi: 10.1360/04wb0031
25. [25]
  Ayhan, M. M.; Karoui, H.; Hardy, M.; Rockenbauer, A.; Charles, R.; Udachin, K.; Tordo, P.; Bardelang, D.; Ouari, O. J.Am.Chem.Soc. 2015. 137, 10238. doi: 10.1021/jacs.5b04553
26. [26]
  Wu, F.; Wu, L. H.; Xiao, X.; Zhang, Y. Q.; Xue, S. F.; Tao, Z.; Day, A. I. J.Org.Chem. 2012, 77, 606. doi: 10.1021/jo2021778
27. [27]
  Zhang, L. M.; Zhu, J. N.; Zhang, Y. Q.; Xue, S. F.; Tao, Z. J.Mol.Struct. 2009, 927, 14. doi: 10.1016/j.molstruc.2009.01.051
28. [28]
  Cheng, X. J.; Liang, L. L.; Chen, K.; Ji, N. N.; Xiao, X.; Zhang, J. X.; Zhang, Y. Q.; Xue, S. F.; Zhu, Q. J.; Ni, X. L.; Tao, Z. Angew.Chem., Int.Ed. 2013, 52, 7252. doi: 10.1002/anie.201210267
29. [29]
  Li, Q.; Qiu, S. C.; Zhang, J.; Chen, K.; Huang, Y.; Xiao, X.; Zhang, Y. Q.; Xue, S. F.; Zhu, Q. J.; Tao, Z.; Lindoy, L. F.; Wei, G. Org.Lett. 2016, 18, 4020. doi: 10.1021/acs.orglett.6b01842
30. [30]
  Chen, P.; Gao, R. H.; Fan, Y.; Xiao, B.; Xue, S. F.; Zhu, Q. J.; Tao, Z. J. Guizhou Univ. (Nat. Sci.) 2016, 33, 27(in Chinese).
31. [31]
  Isaacs, L.; Park, S. K.; Liu, S. M.; Ko, Y. H.; Selvapalam, N.; Kim, Y.; Kim, H.; Zavalij, P. Y.; Kim, G. H.; Lee, H. S.; Kim, K. J.Am.Chem.Soc. 2005, 127, 18000. doi: 10.1021/ja056988k
32. [32]
  Logsdon, L. A.; Schardon, C. L.; Ramalingam, V.; Kwee, S. K.; Urbach, A. R. J.Am.Chem.Soc. 2011, 133, 17087. doi: 10.1021/ja207825y
33. [33]
  Chinai, J. M.; Taylor, A. B.; Ryno, L. M.; Hargreaves, N. D.; Morris, C. A.; Hart, P. J.; Urbach, A. R. J.Am.Chem.Soc. 2011, 133, 8810. doi: 10.1021/ja201581x
34. [34]
  Logsdon, L. A.; Urbach, A. R. J.Am.Chem.Soc. 2013, 135, 11414. doi: 10.1021/ja406032x
35. [35]
  Smith, L. C.; Leach, D. G.; Blaylock, B. E.; Ali, O. A.; Urbach A. R. J.Am.Chem.Soc. 2015, 137, 3663. doi: 10.1021/jacs.5b00718
36. [36]
  Lee, J. W.; Lee, H. H. L.; Ko, Y. H.; Kim, K.; Kim, H. I. J.Phys.Chem.B 2015, 119, 4628. doi: 10.1021/acs.jpcb.5b00743
37. [37]
  Sonzini, S.; Ryan, S. T. J.; Scherman, O. A. Chem.Commun. 2013, 49, 8779. doi: 10.1039/c3cc45420g
38. [38]
  Shan, P. H.; Tu, S. C.; Lin, R. L.; Tao, Z.; Liu, J. X.; Xiao, X. CrystEngComm 2017, 19, 2168. doi: 10.1039/C7CE00340D
39. [39]
  Gao, Z. Z.; Lin, R. L.; Bai, D.; Tao, Z.; Liu, J. X.; Xiao, X. Sci.Rep. 2017, 7, 44717. doi: 10.1038/srep44717
40. [40]
  Li, Q.; Zhang, Y. Q.; Zhu, Q. J.; Xue, S. F.; Tao, Z.; Xiao, X. Chem.-Asian J. 2015, 10, 1159. doi: 10.1002/asia.v10.5
41. [41]
  Day, A. I.; Arnold, A. P. WO 2000068232, 2000[Chem.Abstr. 2000, 133, 362775].
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