两种七元瓜环与3-(2-萘基)-丙氨酸的包结行为分析
收稿日期: 2018-01-13
修回日期: 2018-02-08
网络出版日期: 2018-02-11
基金资助
国家自然科学基金（No.21561007）、贵州省科学基金（No.2016-1030）、贵州省高层次创新型人才培养计划（No.2016-5657）和贵州省教育厅创新群体重大研究（No.黔教合KY字2017-028）资助项目.
Study of the Interaction between Two Kinds of Cucurbit [7]urils and 3-(2-Naphthyl)-alanine
Received date: 2018-01-13
Revised date: 2018-02-08
Online published: 2018-02-11
Supported by
Project 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).
以反式七元瓜环（iQ[7]）和七元瓜环（Q[7]）作为主体分子，一对氨基酸对映体L-3-（2-萘基）-丙氨酸（L-NA）及D-3-（2-萘基）-丙氨酸（D-NA）为客体分子，利用紫外-可见吸收光谱、荧光光谱、等温滴定量热分析、基质辅助激光解吸电离飞行时间质谱以及核磁共振技术等手段，对比探究了这两种具有不同空腔大小的七元瓜环与这一对氨基酸对映体之间的自组装模式的异同点，实验结果表明：这四组主客体包结物具有相同的作用模式，均为瓜环的空腔包结了客体分子的萘环部分而客体分子的氨基及羧酸部分位于瓜环的端口外侧，主客体均以1∶1的作用比相互配位形成较为稳定的超分子自组装体，同时发现两种七元瓜环对L/D-NA手性对映体的分子选择性略有不同.
白东 , 周杨 , 卢季红 , 刘青云 , 陈青 , 陶朱 , 肖昕 . 两种七元瓜环与3-(2-萘基)-丙氨酸的包结行为分析[J]. 有机化学, 2018 , 38(6) : 1477 -1483 . DOI: 10.6023/cjoc201801020
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.
Key words： inverted cucurbit[7]uril; cucurbit[7]uril; enantiomer; amino acid; self-assembly
[1] Peczuh, M. W.; Hamilton, A. D. Chem.Rev. 2000, 100, 2479.
[2] Yin, H.; Hamilton, A. D. Angew.Chem., Int.Ed. 2005, 44, 4130.
[3] Schmuck, C. Coord.Chem.Rev. 2006, 250, 3053.
[4] Urbach, A. R.; Ramalingam, V. Isr.J.Chem. 2011, 55, 664.
[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). (张薇, 徐妮为, 姚子健, 李宽, 朱玉, 陈良艳, 叶文玲, 邓维, 有机化学, 2016, 36, 2039.)
[6] Freeman, W. A.; Mock, W. L.; Shih, N. Y. J.Am.Chem.Soc. 1981, 103, 7367.
[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.
[8] Yi, J. M.; Chen, M. H.; Xue, S. F.; Tao, Z. Chin.J.Org.Chem. 2016, 36, 653(in Chinese). (易君明, 陈明华, 薛赛凤, 陶朱, 有机化学, 2016, 36, 653.)
[9] Yin, Z. J.; Wu, Z. Q.; Lin, F.; Qi, Q. Y.; Xu, X. N.; Zhao, X. Chin.Chem.Lett. 2017, 28, 1167.
[10] Zhang, M.; Gao, J.; Cai, M.; Jiang, J.; Tian, Z. Sci.China, Ser.B:Chem. 2016, 59, 848.
[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] Xiao, X.; Liu, J. X.; Fan, Z. F.; Chen, K.; Zhu, Q. J.; Xue, S. F.; Tao Z. Chem.Commun. 2010, 46, 3741.
[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). (易君明, 肖昕, 张云黔, 薛赛凤, 陶朱, 张建新, 化学学报, 2014, 72, 949.)
[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.
[15] Ni, X. L.; Xiao, X.; Cong, H.; Zhu, Q. J.; Xue, S. F.; Tao, Z. Acc.Chem.Res. 2010, 47, 1386.
[16] Kaifer, A. E. Acc.Chem.Res. 2014, 47, 2160.
[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). (白东, 王鑫, 高中政, 邱胜超, 陶朱, 张建新, 肖昕, 有机化学, 2017, 37, 2022.)
[18] Dong, N.; Wang, X. L.; Pan, J. P.; Tao, Z. Acta Chim.Sinica 2011, 69, 1431(in Chinese). (董南, 王秀林, 盘金品, 陶朱, 化学学报, 2011, 69, 1431.)
[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.
[20] Liu, Q. Y.; Ge, S. S.; Cui, G. W. Acta Crystallogr. 2009, 65, 359.
[21] Li, B.; Li, X.; Sun, X.; Wang, N. Chin. J. Chem. 2016, 34, 1114.
[22] Li, T. T.; Wen, L. L.; Ji, H. L.; Liu, F. Y.; Sun, S. G. Chin.Chem.Lett. 2017, 28, 463.
[23] Freeman, W. A.; Mock, W. L.; Shih, N. Y. J.Am.Chem.Soc. 1981, 103, 7367.
[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.
[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.
[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.
[27] Zhang, L. M.; Zhu, J. N.; Zhang, Y. Q.; Xue, S. F.; Tao, Z. J.Mol.Struct. 2009, 927, 14.
[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.
[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.
[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). (陈鹏, 高瑞晗, 范颖, 肖勃, 薛赛凤, 祝黔江, 陶朱, 贵州大学学报(自然科学版), 2016, 33, 27.)
[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.
[32] Logsdon, L. A.; Schardon, C. L.; Ramalingam, V.; Kwee, S. K.; Urbach, A. R. J.Am.Chem.Soc. 2011, 133, 17087.
[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.
[34] Logsdon, L. A.; Urbach, A. R. J.Am.Chem.Soc. 2013, 135, 11414.
[35] Smith, L. C.; Leach, D. G.; Blaylock, B. E.; Ali, O. A.; Urbach A. R. J.Am.Chem.Soc. 2015, 137, 3663.
[36] Lee, J. W.; Lee, H. H. L.; Ko, Y. H.; Kim, K.; Kim, H. I. J.Phys.Chem.B 2015, 119, 4628.
[37] Sonzini, S.; Ryan, S. T. J.; Scherman, O. A. Chem.Commun. 2013, 49, 8779.
[38] Shan, P. H.; Tu, S. C.; Lin, R. L.; Tao, Z.; Liu, J. X.; Xiao, X. CrystEngComm 2017, 19, 2168.
[39] Gao, Z. Z.; Lin, R. L.; Bai, D.; Tao, Z.; Liu, J. X.; Xiao, X. Sci.Rep. 2017, 7, 44717.
[40] Li, Q.; Zhang, Y. Q.; Zhu, Q. J.; Xue, S. F.; Tao, Z.; Xiao, X. Chem.-Asian J. 2015, 10, 1159.
[41] Day, A. I.; Arnold, A. P. WO 2000068232, 2000[Chem.Abstr. 2000, 133, 362775].
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