Chinese Journal of Organic Chemistry >
Chiral Fluorescent Probes for Determination of Both Concentration and Enantiomeric Composition of Amino Acids
Received date: 2024-01-16
Revised date: 2024-05-08
Online published: 2024-03-28
Supported by
National Natural Science Foundation of China(22074114); National Natural Science Foundation of China(22377097); National Natural Science Foundation of China(21877087); Natural Science Foundation of Hubei Province(2020CFB623); Natural Science Foundation of Hubei Province(2021CFB556); Engineering Research Center of Phosphorus Resources Development and Utilization of Ministry of Education(LCX202305); Wuhan Institute of Technology Graduate Education and Teaching Reform Research Project(2022JYXM09); Wuhan Institute of Technology Graduate Education and Teaching Reform Research Project(2021JYXM07); Graduate Innovative Fund of Wuhan Institute of Technology(CX2022450)
A novel 1,1'-bi-2-naphthol (BINOL)-based fluorescent probe (R)-(E)-2,2'-dihydroxy-3'-((quinolin-7-ylimino)methyl)- [1,1'-binaphthalene]-3-carbaldehyde [(R)-2] and its isomer (R)-(E)-2,2'-dihydroxy-3'-((quinolin-6-ylimino)methyl)-[1,1'- binaphthalene]-3-carbaldehyde [(R)-3] were designed and synthesized. The quinoline imine groups at 3'-position of the probes were involved in the molecular recognition of amino acids through complexation between N atom and Zn(II), which synergically enhanced the enantioselectivity of BINOL-aldehyde to amino acids. The probe molecule exhibited chiral independent fluorescence enhancement for various amino acids at 438 nm, while exhibiting excellent enantioselective fluorescence response at 513 nm. The dependence function of the intensities of the above two emission peaks on arginine concentrations and enantiomeric excess (ee) was studied, and the concentrations and ee values of several arginine samples were measured by the fitted function equation. The interaction mechanism between (R)-2 and D-/L-arginine in the presence of Zn2+ was investigated by 1H NMR and HRMS. The thermodynamic stability of the arginine enantiomer/probe/Zn(II) complexes was calculated by Gaussian 16 program to elucidate the origin of the enantioselectivity. This work affords a platform for the determination of the concentration and enantiomeric composition of 7 amino acids (Glu, Arg, Gln, Ser, Thr, Met, Ala) through a single probe.
Feifan Li , Kang Yu , Chuanzhi Ni , Yuanyuan Zhu , Jie Zeng , Shuangxi Gu . Chiral Fluorescent Probes for Determination of Both Concentration and Enantiomeric Composition of Amino Acids[J]. Chinese Journal of Organic Chemistry, 2024 , 44(6) : 1862 -1869 . DOI: 10.6023/cjoc202401022
| [1] | (a) Vellai, T. Nature 2021, 596, 192. |
| [1] | (b) Oh, S. F.; Praveena, T.; Song, H.; Yoo, J. S.; Jung, D. J.; Erturk-Hasdemi, D.; Hwang, Y. S.; Lee, C. C.; Le Nours, J.; Kim, H.; Lee, J.; Blumberg, R. S.; Rossjohn, J.; Park, S. B.; Kasper, D. L. Nature 2021, 600, 302. |
| [1] | (c) Gu, S.-X.; Wang, H.-F.; Zhu, Y.-Y.; Chen, F.-E. Pharm. Fronts 2020, 2, e79. |
| [2] | (a) Cheng, X.; Shen, C.; Dong, X.-Q.; Wang, C.-J. Chem. Commun. 2022, 58, 3142. |
| [2] | (b) Li, K.; Wang, L.; Zhen, S.; Zhu, L.; Yu, S.; Wu, Y.; Guo, H. Org. Chem. Front. 2023, 10, 5463. |
| [2] | (c) Nie, F.; Wang, K.-Z.; Yan, D. Nat. Commun. 2023, 14, 1654. |
| [2] | (d) Cai, J.; Liu, A.-A.; Shi, X.-H.; Fu, H.; Zhao, W.; Xu, L.; Kuang, H.; Xu, C.; Pang, D.-W. J. Am. Chem. Soc. 2023, 145, 24375. |
| [3] | Reviews on the determination of concentration and enantiomeric composition of amino acids by fluorescent probes: (a) Pu, L. Acc. Chem. Res. 2017, 50, 1032. |
| [3] | (b) Herrera, B. T.; Pilicer, S. L.; Anslyn, E. V.; Joyce, L. A.; Wolf, C. J. Am. Chem. Soc. 2018, 140, 10385. |
| [3] | (c) Yu, F.; Chen, Y.; Jiang, H.; Wang, X. Analyst 2020, 145, 6769. |
| [4] | Researches on the determination of concentration and enantiomeric composition of amino acids by fluorescent probes: (a) Wang, Q.; Wu, X.; Pu, L. Org. Lett. 2019, 21, 9036. |
| [4] | (b) Wen, K.; Yu, S.; Huang, Z.; Chen, L.; Xiao, M.; Yu, X.; Pu, L. J. Am. Chem. Soc. 2015, 137, 4517. |
| [4] | (c) Iqbal, S.; Yu, S.; Jiang, L.; Wang, X.; Chen, Y.; Wang, Y.; Yu, X.; Pu, L. Chem.-Eur. J. 2019, 25, 9967. |
| [5] | Determination of concentration and enantiomeric composition of chiral amines by other methods: (a) Bentley, K. W.; Wolf, C. J. Am. Chem. Soc. 2013, 135, 12200. |
| [5] | (b) Nieto, S.; Lynch, V. M.; Anslyn, E. V.; Kim, H.; Chin, J. J. Am. Chem. Soc. 2008, 130, 9232. |
| [5] | (c) Nieto, S.; Dragna, J. M.; Anslyn, E. V. Chem.-Eur. J. 2010, 16, 227. |
| [6] | Non-BINOL-based chiral fluorescence probes: (a) Mei, X. F.; Wolf, C. Chem. Commun. 2004, 2078. |
| [6] | (b) Upadhyay, S. P.; Pissurlenkar, R. R. S.; Coutinho, E. C.; Karnik, A. V. J. Org. Chem. 2007, 72, 5709. |
| [6] | (c) Ghosn, M. W.; Wolf, C. J. Am. Chem. Soc. 2009, 131, 16360. |
| [7] | Huang, Z.; Yu, S.; Wen, K.; Yu, X.; Pu, L. Chem. Sci. 2014, 5, 3457. |
| [8] | Zhu, Y.-Y.; Wu, X.-D.; Gu, S.-X.; Pu, L. J. Am. Chem. Soc. 2019, 141, 175. |
| [9] | Achiral fluorescent probes of Zn(II) with quinoline groups: (a) Hsieh, W. H.; Wan, C.-F.; Liao, D.-J.; Wu, A.-T. Tetrahedron Lett. 2012, 53, 5848. |
| [9] | (b) Kimura, E.; Koike, T. Chem. Soc. Rev. 1998, 27, 179. |
| [9] | (c) Zalewski, P. D.; Forbes, I. J.; Seamark, R. F.; Borlinghaus, R.; Betts, W. H.; Lincoln, S. F.; Ward, A. D. Chem. Biol. 1994, 1, 153. |
| [9] | (d) Zalewski, P. D.; Forbes, I. J.; Betts, W. H. Biochem. J. 1993, 296, 403. |
| [9] | (e) Huang, S.; Yang, B.; Tu, S. Comput. Theor. Chem. 2022, 1210, 113647. |
| [9] | (f) Gao, L.-L.; Li, S.-P.; Wang, Y.; Wu, W.-N.; Zhao, X.-L.; Li, H.-J.; Xu, Z.-H. Spectrochim. Acta, Part A 2020, 230, 118025. |
/
| 〈 |
|
〉 |
