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

doi:10.6023/cjoc201801020

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (6): 1477-1483.DOI: 10.6023/cjoc201801020 Previous Articles Next Articles

Special Issue: 有机超分子化学合辑

Articles

两种七元瓜环与3-(2-萘基)-丙氨酸的包结行为分析

白东^a, 周杨^b, 卢季红^a, 刘青云^c, 陈青^a, 陶朱^a, 肖昕^a

a 贵州大学贵州省大环化学及超分子化学重点实验室贵阳 550025;
b 山东师范大学化学化工与材料科学学院济南 250014;
c 山东科技大学化学与环境工程学院青岛 266590

收稿日期:2018-01-13 修回日期:2018-02-08 发布日期:2018-02-11
通讯作者: 肖昕,E-mail:gyhxxiaoxin@163.com E-mail:gyhxxiaoxin@163.com
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

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

Received:2018-01-13 Revised:2018-02-08 Published:2018-02-11
Contact: 10.6023/cjoc201801020 E-mail:gyhxxiaoxin@163.com
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).

1. Study of the Interaction between Two Kinds of Cucurbit [7]urils and 3-(2-Naphthyl)-alanine.PDF(2045KB)

Abstract

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

Cite this article

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]. Chin. J. Org. Chem., 2018, 38(6): 1477-1483.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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].

两种七元瓜环与3-(2-萘基)-丙氨酸的包结行为分析

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

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Wenjie Zhu, Zhenchuang Xu, Yu-Cheng Gu, Yanchuan Zhao. Research Progress on Organic Cation Receptors Based on Molecular Containers [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 2991-3005.
[2]	Haoruo Shangguan, Ping Huang, Zhenya Dai, Ping Wang. Synthesis and Application of β-Thiolated Amino Acids [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3089-3097.
[3]	Zhangtao Zhou, Yang Wang, Bingxin Cheng, Weiping Ye. [RuCl(p-cymene)-(S)-BINAP]Cl Catalyzed Asymmetric Preparation of trans-3-Amino-bicyclo[2.2.2]octane-2-carboxylic Acid Ethyl Ester [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2961-2967.
[4]	Sifan Dong, Haolong Li, Yuan Qin, Shiming Fan, Shouxin Liu. Research Progress of Amino Acids as Transient Directing Groups in C—H Bond Activation Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2351-2367.
[5]	Fen Li, Chuanzhi Liu, Zhiyuan Hu, Panpan Luo, Rongzheng Cui, Yanke Huang, Xinming Liu, Lantao Liu, Wei Wu. Intermolecular Halogen and Hydrogen Bonding-Controlled Self-Assembly of Network Structures [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 705-711.
[6]	Yongling Wang, Tiexin Zhang, Xuming Zhang, Hanyang Sun, Jinyao Leng, Yaming Li. Synthesis of Unnatural Amino Acid Derivatives by Visible- Light-Catalyzed Decarboxylative Alkylation of N-Aromatic Glyoxylimines [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4284-4293.
[7]	Na Li, Xiaofeng Tan, Qinglai Yang. Recent Progress on Strategies and Applications of Imaging for Intestinal Microflora [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1375-1386.
[8]	Jiayu Hu, Zhiqiang Zhu, Zongbo Xie, Zhanggao Le. Recent Advances in Visible-Light-Induced Decarboxylative Coupling Reactions of α-Amino Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 978-1001.
[9]	Ting Wang, Jingchao Chen, Lun Wang, Zheting Wang, Baomin Fan. Asymmetric Transfer Hydrogenation of α-Aryl Amidates Using Methanol as Hydrogen Source [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3693-3703.
[10]	Nana Wang, Jingcheng Xu, Haibo Mei, Hiroki Moriwaki, Kunisuke Izawa, Vadim A. Soloshonok, Jianlin Han. Electrochemical Approaches for Preparation of Tailor-Made Amino Acids [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3034-3049.
[11]	Hongyu Qian, Pin He, Lu Zhang, Ke Chen, Binbin Xu, Shaoliang Lin. Synthesis and Photo-responsive Self-Assembly of Azobenzene-Containing Molecular Brushes [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2891-2897.
[12]	Changxing Ji, Guangxia Wang, Hua Wang. Progress in Metal-Organic Supramolecular System Based on Subcomponent Self-Assembly [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2261-2279.
[13]	Li Sheng, Haoling Gao, Xufeng Wu, Gang Fan, Pengcheng Liu. Rhodium/(2S,2'S,3S,3'S)-3,3'-Di-tert-butyl-4,4'-dimethoxy-2,2',3,3'-tetrahydro-2,2'-bibenzo[d][1,3]oxaphosphole (MeO-BIBOP) Catalyzed Synthesis of (R)-3-tert-Butoxy-carbonylamino-4-(2,4,5-trifluorophenyl)butyric Acid by Asymmetric Reduction of Enamines [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2105-2111.
[14]	Han Ren, Ruxiang Li, Zhijian Chen, Lili Li, Hao Wang. Modification Methods and Applications of Self-Assembly Peptides [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3983-3994.
[15]	Qiang Pei, Aixiang Ding, Jinjin Wu. Supramolecular Assemblies Based on Intramolecular Three-Center Hydrogen Bond and their Applications [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 105-125.