Citation: Chen Jian-Yu, Xiao Qi, Behera Harekrushna, Hou Jun-Li. Unimolecular artificial transmembrane channel with terminal dihydrogen phosphate groups showing transport selectivity for ammonium[J]. Chinese Chemical Letters, ;2020, 31(1): 77-80. doi: 10.1016/j.cclet.2019.05.009 shu

Unimolecular artificial transmembrane channel with terminal dihydrogen phosphate groups showing transport selectivity for ammonium

Department of Chemistry, Fudan University, Shanghai 200433, China

houjl@fudan.edu.cn

Received Date: 26 March 2019
Revised Date: 17 April 2019
Accepted Date: 6 May 2019
Available Online: 6 January 2019

Figures(4)

A new artificial transmembrane channel molecule bearing dihydrogen phosphate groups has been synthesized. The terminal dihydrogen phosphate groups enable the channel to be highly negatively charged at both ends of the channel structures. The artificial channel could incorporate into the lipid bilayer efficiently under low concentration. The channel displays high NH₄⁺/K⁺ selectivity due to the electrostatic interaction and hydrogen bonding between NH₄⁺ and the terminal dihydrogen phosphate groups.
- Artificial transmembrane channel,
- Ammonium transport,
- Dihydrogen phosphate,
- Pillar[5]arene,
- Transmembrane transport,
- Transport selectivity
1. [1]
  B. Hille, Ionic Channels of Excitable Membranes, 3rd ed., Sinauer Associates, Sunderland, MA, 2001.
2. [2]
  D.A. Doyle, J. Morais Cabral, R.A. Pfuetzner, et al., Science 280(1998) 69-77. doi: 10.1126/science.280.5360.69
3. [3]
  G.W. Gokel, O. Murillo, Acc. Chem. Res. 29(1996) 425-432. doi: 10.1021/ar9601353
4. [4]
  T.M. Fyles, Chem. Soc. Rev. 36(2007) 335-347. doi: 10.1039/B603256G
5. [5]
  S. Matile, A.V. Jentzsch, J. Montenegro, A. Fin, Chem. Soc. Rev. 40(2011) 2453-2474. doi: 10.1039/c0cs00209g
6. [6]
  J. Montenegro, M.R. Ghadiri, J.R. Granja, Acc. Chem. Res. 46(2013) 2955-2965. doi: 10.1021/ar400061d
7. [7]
  B. Gong, Z. Shao, Acc. Chem. Res. 46(2013) 2856-2866. doi: 10.1021/ar400030e
8. [8]
  Y. Zhao, H. Cho, L. Widdanapathirana, S. Zhang, Acc. Chem. Res. 46(2013) 2763-2772. doi: 10.1021/ar300337f
9. [9]
  M. Barboiu, A. Gilles, Acc. Chem. Res. 46(2013) 2814-2823. doi: 10.1021/ar400025e
10. [10]
  Y. Huo, H. Zeng, Acc. Chem. Res. 49(2016) 922-930. doi: 10.1021/acs.accounts.6b00051
11. [11]
  M. Barboiu, Y.L. Duc, A. Gilles, et al., Nat. Commun. 5(2014) 4142-4149. doi: 10.1038/ncomms5142
12. [12]
  X. Wu, L. Gao, J. Sun, X. Hu, L. Wang, Chin. Chem. Lett. 27(2016) 1655-1660. doi: 10.1016/j.cclet.2016.05.004
13. [13]
  T. Xiao, L. Zhou, L. Xu, et al., Chin. Chem. Lett. 30(2019) 271-276. doi: 10.1016/j.cclet.2018.05.039
14. [14]
  B. Bai, Y. Fang, Q. Gan, et al., Chin. J. Chem. 33(2015) 361-367. doi: 10.1002/cjoc.201400899
15. [15]
  X. Lou, H. Chen, X. Jia, C.J. Li, Chin. J. Chem. 33(2015) 335-338. doi: 10.1002/cjoc.201400889
16. [16]
  L. Liu, W. Duan, Y. Kou, et al., Chin. J. Chem. 33(2015) 346-350. doi: 10.1002/cjoc.201400879
17. [17]
  G.W. Gokel, A. Mukhopadhyay, Chem. Soc. Rev. 30(2001) 274-286. doi: 10.1039/b008667n
18. [18]
  J.K.W. Chui, T.M. Fyles, Chem. Soc. Rev. 41(2012) 148-175. doi: 10.1039/C1CS15099E
19. [19]
  D.W. Urry, M.C. Goodall, J.D. Glickson, D.F. Mayers, Proc. Natl. Acad. Sci. U. S. A. 68(1971) 1907-1911. doi: 10.1073/pnas.68.8.1907
20. [20]
  C.J. Stankovic, S.H. Heinemann, J.M. Delfino, F.J. Sigworth, S.L. Schreiber, Science 244(1989) 813-817. doi: 10.1126/science.2471263
21. [21]
  M.J. Pregel, L. Jullien, J. Canceill, L. Lacombe, J.M. Lehn, J. Chem. Soc. Perkin Trans. 2(1995) 417-426.
22. [22]
  A. Schrey, A. Vescovi, A. Knoll, C. Rickert, U. Koert, Angew. Chem. Int. Ed. 39(2000) 900-902. doi: 10.1002/(SICI)1521-3773(20000303)39:5<900::AID-ANIE900>3.0.CO;2-D
23. [23]
  A. Matsubara, K. Asami, A. Akagi, N. Nishino, Chem. Commun. (1996) 2069-2070.
24. [24]
  G.W. Gokel, S. Negin, Acc. Chem. Res. 46(2013) 2824-2833. doi: 10.1021/ar400026x
25. [25]
  W. Si, P. Xin, Z.T. Li, J.L. Hou, Acc. Chem. Res. 48(2015) 1612-1619. doi: 10.1021/acs.accounts.5b00143
26. [26]
  L. Chen, W. Si, L. Zhang, et al., J. Am. Chem. Soc. 135(2013) 2152-2155. doi: 10.1021/ja312704e
27. [27]
  P. Xin, P. Zhu, P. Su, J.L. Hou, Z.T. Li, J. Am. Chem. Soc. 136(2014) 13078-13081. doi: 10.1021/ja503376s
28. [28]
  P. Xin, L. Zhang, P. Su, J.L. Hou, Z.T. Li, Chem. Commun. 51(2015) 4819-4822. doi: 10.1039/C5CC00691K
29. [29]
  T. Ogoshi, S. Kanai, S. Fujinami, T.A. Yamagishi, Y. Nakamoto, J. Am. Chem. Soc. 130(2008) 5022-5023. doi: 10.1021/ja711260m
30. [30]
  T. Ogoshi, T.A. Yamagishi, Y. Nakamoto, Chem Rev. 116(2016) 7937-8002. doi: 10.1021/acs.chemrev.5b00765
31. [31]
  W. Si, P. Xin, Z.T. Li, J.L. Hou, Acc. Chem. Res. 48(2015) 1612-1619. doi: 10.1021/acs.accounts.5b00143
32. [32]
  M. Xue, Y. Yang, X.D. Chi, Z.B. Zhang, F. Huang, Acc. Chem. Res. 45(2012) 1294-1308. doi: 10.1021/ar2003418
33. [33]
  Y. Yao, M. Xue, J. Chen, M. Zhang, F. Huang, J. Am. Chem. Soc. 134(2012) 15712-15715. doi: 10.1021/ja3076617
34. [34]
  Y. Ma, X. Chi, X. Yan, et al., Org Lett. 14(2012) 1532-1535. doi: 10.1021/ol300263z
35. [35]
  T. Ogoshi, M. Hashizume, T.A. Yamagishi, Y. Nakamoto, Chem. Commun. 46(2010) 3708-3710. doi: 10.1039/c0cc00348d
36. [36]
  C. Han, F. Ma, Z. Zhang, et al., Org. Lett. 12(2010) 4360-4363. doi: 10.1021/ol1018344
37. [37]
  W. Si, X.B. Hu, X.H. Liu, et al., Tetrahedron Lett. 52(2011) 2484-2487. doi: 10.1016/j.tetlet.2011.03.019
38. [38]
  M. Wang, X. Du, H. Tian, et al., Chin. Chem. Lett. 30(2019) 345-348. doi: 10.1016/j.cclet.2018.10.014
39. [39]
  C. Park, K.T. Kim, Chin. J. Chem. 33(2015) 311-318. doi: 10.1002/cjoc.201400875
40. [40]
  Y.J. Zhou, Y. Yao, F. Huang, Chin. J. Chem. 33(2015) 356-360. doi: 10.1002/cjoc.201400697
41. [41]
  Y.M. Zhang, J. Su, Q. Li, et al., Chin. J. Chem. 34(2016) 1263-1267. doi: 10.1002/cjoc.201600588
42. [42]
  V. Fonseca, P. Daumas, L. Ranjalahy-Rasoloarijao, et al., Biochemistry 31(1992) 5340-5350. doi: 10.1021/bi00138a014
43. [43]
  A.A. Seoh, D. Busath, Biophys. J. 68(1995) 2271-2279. doi: 10.1016/S0006-3495(95)80409-1
44. [44]
  M.R. Ghadiri, J.R. Granja, L.K. Buehler, Nature 369(1994) 301-304. doi: 10.1038/369301a0
45. [45]
  Y.J. Jeon, H. Kim, S. Jon, et al., J. Am. Chem. Soc. 126(2004) 15944-15945. doi: 10.1021/ja044748j
46. [46]
  K. Kano, J.H. Fendler, Biochim. Biophys. Acta Biomembr. 509(1978) 289-299. doi: 10.1016/0005-2736(78)90048-2
47. [47]
  N.R. Clement, J.M. Gould, Biochemistry 20(1981) 1534-1538. doi: 10.1021/bi00509a019
48. [48]
  N. Busschaert, M. Wenzel, M.E. Light, et al., J. Am. Chem. Soc. 133(2011) 14136-14148. doi: 10.1021/ja205884y
49. [49]
  S. Matile, N. Sakai, A. Hennig, Transport experiments in membranes, in: P.A. Gale, J.W. Steed (Eds.), Supramolecular Chemistry: From Molecules to Nanomaterials, vol. 2, Wiley, Chichester, 2012 p. 473.
50. [50]
  R.H. Ashley, Ion Channels: A Practical Approach, Oxford University Press, Oxford, 1995.
51. [51]
  J.K.W. Chui, T.M. Fyles, Chem. Soc. Rev. 41(2012) 148-175. doi: 10.1039/C1CS15099E
52. [52]
  T.M. Fyles, D. Loock, W.F. van Straaten-Nijenhuis, X. Zhou, J. Org. Chem. 61(1996) 8866-8874. doi: 10.1021/jo961267c
53. [53]
  G. Eisenman, R.J. Horn, Membr. Biol. 76(1983) 197-225. doi: 10.1007/BF01870364
54. [54]
  E. Neher, J. Sandblom, G.J. Eisenman, Membr. Biol. 40(1978) 97-116. doi: 10.1007/BF01871143
55. [55]
  B.W. Urban, S.B. Hladky, D.A. Haydon, Biochim. Biophys. Acta 602(1980) 331-354. doi: 10.1016/0005-2736(80)90316-8
1. [1]
  Bingbing Shi , Yuchun Wang , Yi Zhou , Xing-Xing Zhao , Yizhou Li , Nuoqian Yan , Wen-Juan Qu , Qi Lin , Tai-Bao Wei . A supramolecular oligo[2]rotaxane constructed by orthogonal platinum(Ⅱ) metallacycle and pillar[5]arene-based host–guest interactions. Chinese Chemical Letters, 2024, 35(10): 109540-. doi: 10.1016/j.cclet.2024.109540
2. [2]
  Brandon Bishop , Shaofeng Huang , Hongxuan Chen , Haijia Yu , Hai Long , Jingshi Shen , Wei Zhang . Artificial transmembrane channel constructed from shape-persistent covalent organic molecular cages capable of ion and small molecule transport. Chinese Chemical Letters, 2024, 35(11): 109966-. doi: 10.1016/j.cclet.2024.109966
3. [3]
  Ting-Ting Huang , Jin-Fa Chen , Juan Liu , Tai-Bao Wei , Hong Yao , Bingbing Shi , Qi Lin . A novel fused bi-macrocyclic host for sensitive detection of Cr₂O₇²⁻ based on enrichment effect. Chinese Chemical Letters, 2024, 35(7): 109281-. doi: 10.1016/j.cclet.2023.109281
4. [4]
  Jia-hui Li , Jinkai Qiu , Cheng Lian . Lithium-ion rapid transport mechanism and channel design in solid electrolytes. Chinese Journal of Structural Chemistry, 2025, 44(1): 100381-100381. doi: 10.1016/j.cjsc.2024.100381
5. [5]
  Lei Zhou , Youjun Zhou , Lizhen Fang , Yiqiao Bai , Yujia Meng , Liang Li , Jie Yang , Yong Yao . Pillar[5]arene based artificial light-harvesting supramolecular polymer for efficient and recyclable photocatalytic applications. Chinese Chemical Letters, 2024, 35(9): 109509-. doi: 10.1016/j.cclet.2024.109509
6. [6]
  Hui Li , Yanxing Qi , Jia Chen , Juanjuan Wang , Min Yang , Hongdeng Qiu . Synthesis of amine-pillar[5]arene porous adsorbent for adsorption of CO₂ and selectivity over N₂ and CH₄. Chinese Chemical Letters, 2024, 35(11): 109659-. doi: 10.1016/j.cclet.2024.109659
7. [7]
  Yinglan Yu , Sajid Hussain , Jianping Qi , Lei Luo , Xuemei Zhang . Mechanisms and applications: Cargos transport to basolateral membranes in polarized epithelial cells. Chinese Chemical Letters, 2024, 35(12): 109673-. doi: 10.1016/j.cclet.2024.109673
8. [8]
  Kai Han , Guohui Dong , Ishaaq Saeed , Tingting Dong , Chenyang Xiao . Boosting bulk charge transport of CuWO4 photoanodes via Cs doping for solar water oxidation. Chinese Journal of Structural Chemistry, 2024, 43(2): 100207-100207. doi: 10.1016/j.cjsc.2023.100207
9. [9]
  Shaonan Liu , Shuixing Dai , Minghua Huang . The impact of ester groups on 1,8-naphthalimide electron transport material in organic solar cells. Chinese Journal of Structural Chemistry, 2024, 43(6): 100277-100277. doi: 10.1016/j.cjsc.2023.100277
10. [10]
  Rongjun Zhao , Tai Wu , Yong Hua , Yude Wang . Improving performance of perovskite solar cells enabled by defects passivation and carrier transport dynamics regulation via organic additive. Chinese Chemical Letters, 2025, 36(2): 109587-. doi: 10.1016/j.cclet.2024.109587
11. [11]
  Yue Zheng , Tianpeng Huang , Pengxian Han , Jun Ma , Guanglei Cui . Cathodal Li-ion interfacial transport in sulfide-based all-solid-state batteries: Challenges and improvement strategies. Chinese Journal of Structural Chemistry, 2024, 43(10): 100390-100390. doi: 10.1016/j.cjsc.2024.100390
12. [12]
  Hao Zhang , Haonan Qu , Ehsan Bahojb Noruzi , Haibing Li , Feng Liang . A nanocomposite film with layer-by-layer self-assembled gold nanospheres driven by cucurbit[7]uril for the selective transport of L-tryptophan and lysozyme. Chinese Chemical Letters, 2025, 36(1): 109731-. doi: 10.1016/j.cclet.2024.109731
13. [13]
  Jiangqi Ning , Junhan Huang , Yuhang Liu , Yanlei Chen , Qing Niu , Qingqing Lin , Yajun He , Zheyuan Liu , Yan Yu , Liuyi Li . Alkyl-linked TiO2@COF heterostructure facilitating photocatalytic CO2 reduction by targeted electron transport. Chinese Journal of Structural Chemistry, 2024, 43(12): 100453-100453. doi: 10.1016/j.cjsc.2024.100453
14. [14]
  Fei Jin , Bolin Yang , Xuanpu Wang , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Facilitating efficient photocatalytic hydrogen evolution via enhanced carrier migration at MOF-on-MOF S-scheme heterojunction interfaces through a graphdiyne (CnH2n-2) electron transport layer. Chinese Journal of Structural Chemistry, 2023, 42(12): 100198-100198. doi: 10.1016/j.cjsc.2023.100198
15. [15]
  Boyuan Hu , Jian Zhang , Yulin Yang , Yayu Dong , Jiaqi Wang , Wei Wang , Kaifeng Lin , Debin Xia . Dual-functional POM@IL complex modulate hole transport layer properties and interfacial charge dynamics for highly efficient and stable perovskite solar cells. Chinese Chemical Letters, 2024, 35(7): 108933-. doi: 10.1016/j.cclet.2023.108933
16. [16]
  Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
17. [17]
  Lingna Wang , Chenxin Tian , Ruobin Dai , Zhiwei Wang . Eco-friendly regeneration of end-of-life PVDF membrane with triethyl phosphate: Efficiency and mechanism. Chinese Chemical Letters, 2024, 35(9): 109356-. doi: 10.1016/j.cclet.2023.109356
18. [18]
  Xinxiu Yan , Xizhe Huang , Yangyang Liu , Weishang Jia , Hualin Chen , Qi Yao , Tao Chen . Hyperbranched polyamidoamine protective layer with phosphate and carboxyl groups for dendrite-free Zn metal anodes. Chinese Chemical Letters, 2024, 35(10): 109426-. doi: 10.1016/j.cclet.2023.109426
19. [19]
  Qijun Tang , Wenguang Tu , Yong Zhou , Zhigang Zou . High efficiency and selectivity catalyst for photocatalytic oxidative coupling of methane. Chinese Journal of Structural Chemistry, 2023, 42(12): 100170-100170. doi: 10.1016/j.cjsc.2023.100170
20. [20]
  Rui HUANG , Shengjie LIU , Qingyuan WU , Nanfeng ZHENG . Enhanced selectivity of catalytic hydrogenation of halogenated nitroaromatics by interfacial effects. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 201-212. doi: 10.11862/CJIC.20240356

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(1035)
HTML views(90)

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