Synthesis and application of chelated complexes [Zn(L-arg)2(H2O)] and [[Zn(L-arg)2(H2O)](SO4)]2– as chiral selectors

Мұқаба

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат Ашық рұқсат
Рұқсат жабық Рұқсат берілді
Рұқсат жабық Тек жазылушылар үшін

Аннотация

By interaction of compounds Zn(II) and L-arginine (L-Arg) the chelated complexes [Zn(L-arg)2(H2O)] (I) and [[Zn(L-arg)2(H2O)](SO4)]2– (II) (L-arg is a deprotonated form of L-Arg) were synthesized. The structure of the obtained complexes was established by IR spectroscopy by comparing the experimental and theoretical IR spectra using quantum chemical modeling. Complexes I and II were studied as chiral selectors of enantioselective voltammetric sensors. It was shown that I exhibits better enantioselective compared to II. By DFT method, it was found that the difference in the exhibited enantioselectivity of complexes I and II can be due of the geometric isomerism of chelate compounds and the peculiarities of the coordination of the obtained complexes with the analyte molecule.

Толық мәтін

Рұқсат жабық

Авторлар туралы

R. Gizatov

Ufa University of Science and Technology

Email: berestovatv@gmail.com
Ресей, Ufa

Yu. Teres

Ufa University of Science and Technology

Email: berestovatv@gmail.com
Ресей, Ufa

M. Galimov

Ufa University of Science and Technology

Email: berestovatv@gmail.com
Ресей, Ufa

E. Bulysheva

Ufa University of Science and Technology

Email: berestovatv@gmail.com
Ресей, Ufa

T. Berestova

Ufa University of Science and Technology

Хат алмасуға жауапты Автор.
Email: berestovatv@gmail.com
Ресей, Ufa

R. Zilberg

Ufa University of Science and Technology

Email: berestovatv@gmail.com
Ресей, Ufa

Әдебиет тізімі

  1. Wojciechowska A., Janczak J., Rytlewski P. et al. // J. Mol. Struct. 2023. V. 1276. P. 134776.
  2. Fita I., Campos J.L., Puigjaner L.C. et al. // J. Mol. Biol. 1983. V. 167. P. 157.
  3. Yamauchi O., Odani A., Takani M. // Dalton Trans. 2002. V. 18. P. 3411.
  4. Chow S.T., McAuliffe C.A. // J. Inorg. Nucl. Chem. 1975. V. 37. № 4. P. 1059.
  5. Altowyan M.S., Yousri A., Albering J.H. et al. // Crystals. 2023. V. 13. № 9. P. 1375
  6. Tainer J.A., Getzoff E.D., Richardson J.S., Richardson D.C. // Nature. 1983. V. 306. № 5940. P. 284.
  7. Getzoff E.D., Tainer J.A., Weiner P.K. et al. // Nature. 1983. V. 306. № 5940. P. 287.
  8. Zil’berg R.A., Zagitova L.R., Vakulin I.V. et al. // J. Anal. Chem. 2021. V. 76. Р. 1438.
  9. Yarkaeva Y.A., Maistrenko V.N., Zagitova L.R. et al. // J. Electroanal. Chem. 2021. V. 903. Р. 115839.
  10. Maistrenko V.N., Zil’berg R. // J. Anal. Chem. 2020. V. 75. Р. 1514.
  11. Maistrenko V.N., Sidel’nikov A.V., Zil’berg R.A. // J. Anal. Chem. 2018. V. 73. Р. 1.
  12. Zou J., Zhao G.-Q., Zhao G.-L., Yu J.-G. // Coord. Chem. Rev. 2022. V. 471. Р. 214732.
  13. Niu X., Yang X., Li H., Liu J., Liu Z., Wang K. // Microchim. Acta. 2020. V. 187. Р. 676.
  14. Salinas G., Niamlaem M., Kuhn A. Arnaboldi S. // Curr. Opin. Colloid Interface Sci. 2022. V. 61. Р. 101626.
  15. Laurie S.H. Handbook of Metal–Ligand Interactions in Biological Fluids — Bioinorganic Chemistry. New York, 1995. V. 1. P. 603.
  16. Clarke E.R., Martell A.E. // J. Inorg. Nucl. Chem. 1970. V. 32. № 3. P. 911.
  17. Bottari E., Festa M.R., Gentile L. // Monatsh. Chem. 2014. V. 145. P. 1707.
  18. Deschamps P., Kulkarni P.P., Sarkar B.X. // Inorg. Chem. V. 43. № 11. P. 2004
  19. Schug K.A., Lindner W. // Chem. Rev. 2005. V. 105. P. 67.
  20. Ohata N., Masuda H., Yamauchi O. // Kobunshi Ronbunshu. 2000. V. 57. № 4. P. 167.
  21. Ohata N., Masuda H., Yamauchi O. // Inorg. Chim. Acta. 2000. V. 300–302. P. 749.
  22. Ohata N., Masuda H., Yamauchi O. // Inorg. Chim. Acta. 1999. V. 286. P. 37.
  23. Duarte M.T.L.S., Carrondo M.A.A.F.D.C.T., Simões Gonçalves M.L.S. et al. // Inorg. Chim. Acta. 1986. V. 124. P. 41.
  24. Musioł1 K., Janczak J., Helios K. et al. // Res. Chem. Intermed. 2023. V. 49. P. 3563.
  25. Yamauchi O., Odani A., Takanic M. // Dalton Trans. 2002. P. 3411.
  26. Ohata N., Masuda H., Yamauchi O. // Angew. Chem. Int. Ed. 1996. V. 35. P. 531.
  27. Alikhani M., Hakimi M., Moeini K. et al. // J. Inorg. Organomet. Polym. 2020. V. 30. P. 2907.
  28. Köse D.A., Toprak E., Avcl E., Avcl G.A. // J. Chin. Chem. Soc. 2014. V. 61 P. 881.
  29. Wojciechowska A., Kochel A., Duczmal M. // Mater. Chem. Phys. 2016. V. 182. P. 472.
  30. Alagha A., Brown D.A., Elawad M et al. // Inorg. Chim. Acta. 2011. V. 377 P. 185.
  31. Zilberg R.A., Teres J.B., Bulysheva E.O. et al. // Electrochim. Acta. 2024. V. 492. Р. 144334.
  32. Zilberg R.A., Berestova T.V., Gizatov R.R. et al. // Inorganics. 2022. V. 10. Р. 117.
  33. Yang M.-X., Zhou M.-J., Cao J.-P. // RSC Adv. 2020. V. 10. Р. 13759.
  34. Chen X., Zhang S., Shan X. et al. // Anal. Chim. Acta. 2019. V. 1072. P. 54.
  35. Zilberg R.A., Teres Y.B., Zagitova L.R. et al. // Anal. Control. 2021. V. 25. Р. 193.
  36. Berestova T.V., Khursan S.L., Mustafin A.G. // J. Spectrochim. Acta. 2020. V. 229. Р. 117950.
  37. Berestova T.V., Gizatov R.R., Galimov M.N., Mustafin A.G. //J. Mol. Struct. 2021. V. 1236. Р. 130303.
  38. Zhao Y., Truhlar D.G. // J. Theor. Chem. Acc. 2008. V. 120. Р. 215.
  39. Yoon U., Kim J., Kim S.H., Jeong K. // RSC Adv. 2024. V. 14. Р. 1051.
  40. Frisch M.J., Trucks G.W., Schlegel H.B. et al. Gaussian 09. Revision D.01. Wallingford (CT): Gaussian Inc., 2016. https://gaussian.com/g09citation
  41. Andrienko G.A. Chemcraft — graphical software for visualization of quantum chemistry computations. Version 1.8, build 682. https://www.chemcraftprog.com
  42. Hu C., Xiang C., Zhangqiang Y. Patent CN108383746A, 2018, C07C 229/76, C07C 227/18.
  43. Berestova T.V., Kuzina L.G., Amineva N.A. et al. // J. Mol. Struct. 2017. V. 1137. P. 260.
  44. Kolesov S.V., Gurinaand M.S., Mudarisova R.K. // Polym. Sci. A. 2019. V. 61. P. 253.
  45. Berestova T.V., Nosenko K.N., Lusina O.V. et al. // J. Struct. Chem. 2020. V. 61. P. 1876.

Қосымша файлдар

Қосымша файлдар
Әрекет
1. JATS XML
2. Fig. 1. Energy parameters of trans- and cis-isomers of the [Zn(L-arg)2(H2O)] complex.

Жүктеу (138KB)
3. Fig. 2. Experimental (red) and theoretical (black) IR spectra of trans- and cis-dimensions of the [Zn(L-arg)2(H2O)] complex in the region of characteristic absorption bands.

Жүктеу (262KB)
4. Fig. 3. Experimental (blue) and theoretical (black) IR spectra of complexes IIa (a) and IIb (b) in the region of characteristic absorption bands.

Жүктеу (247KB)
5. Fig. 4. Differential-pulse voltammograms of 1 mM solutions of enantiomers of biologically active substances on different electrodes: (a, b, c) GCE/PEC-trans-[Zn(L-arg)2(H2O)] and (d, d, e) GCE/PEC-cis-[[Zn(L-arg)2(H2O)](SO4)]2− (phosphate buffer solution with pH 6.86, potential scan rate 0.2 V/s).

Жүктеу (363KB)
6. Fig. 5. Quatovochemical modeling of the intermediates trans-[[Zn(L-arg)2(H2O)](SO4)]2– (a), cis-[[Zn(L-arg)2(H2O)](SO4)]2– (b), trans-[Zn(L-arg)2(H2O)] Tyr (c) and cis-[Zn(L-arg)2(H2O)] Tyr (d).

Жүктеу (346KB)
7. Fig. 6. Energy parameters of the intermediates trans-[[Zn(L-arg)2(H2O)](SO4)]2– and cis-[[Zn(L-arg)2(H2O)](SO4)]2– (a), trans-[Zn(L-arg)2(H2O)] Tyr and cis-[Zn(L-arg)2(H2O)] Tyr (b).

Жүктеу (332KB)
8. Scheme 1. Synthesis of complexes [Zn(L-arg)2(H2O)] (I) and [[Zn(L-arg)2(H2O)](SO4)]2– (II).

Жүктеу (110KB)

© Российская академия наук, 2025