Cyclization of l-leucyl-l-valine dipeptide in the crystal phase under non-isоthermal conditions

Capa

Citar

Texto integral

Acesso aberto Acesso aberto
Acesso é fechado Acesso está concedido
Acesso é fechado Acesso é pago ou somente para assinantes

Resumo

Thermal treatment of linear dipeptides in the solid phase makes it possible to obtain their cyclic analogues in high yield and without additional costs. At the same time, such reactions occurring under the constraints of a crystal lattice with the participation of molecules in the zwitterionic form have not been sufficiently studied. In this work, the cyclization reaction of the dipeptide L-leucyl-L-valine in the crystalline phase upon heating was studied. Using isoconversion kinetics approaches, a kinetic model describing this process is determined, and kinetic parameters are calculated, including activation energy, Arrhenius multiplier, and reaction order. The enantiomeric purity of the resulting cyclic product was assessed. The self-assembly of linear and cyclic dipeptides on a solid support was studied. The results of the study will be useful for establishing the mechanism of the cyclization reaction of dipeptides in the solid phase, and can also be used in the development of effective and cost-effective methods for the production of cyclic dipeptides.

Sobre autores

R. Larionov

A.M. Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University

S. Ziganshina

A.M. Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University;E.K. Zavoisky Kazan Institute of Physics and Technology, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”

A. Klimovitski

A.M. Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University

Kh. Khayarov

A.M. Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University

O. Babaeva

A.E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”

V. Gorbachuk

A.M. Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University

M. Ziganshin

A.M. Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University;Academy of Sciences of the Republic of Tatarstan

Email: marat.ziganshin@kpfu.ru

Bibliografia

  1. Zhao K., Xing R., Yan X. // Peptide Sci. 2021. Vol. 113. Article ID e24202. doi: 10.1002/pep2.24202
  2. Antipin I.S., Alfimov M.V., Arslanov V.V., Burilov V.A., Vatsadze S.Z., Voloshin Ya.Z., Volcho K.P., Gorbatchuk V.V., Gorbunova Yu.G., Gromov S.P., Dudkin S.V., Zaitsev S.Yu., Zakharova L.Ya., Ziganshin M.A., Zolotukhina A.V., Kalinina M.A., Karakhanov E.A., Kashapov R.R., Koifman O.I., Konovalov A.I., Korenev V.S., Maksimov A.L., Mamardashvili N.Zh., Mamardashvili G.M., Martynov A.G., Mustafina A.R., Nugmanov R.I., Ovsyannikov A.S., Padnya P.L., Potapov A.S., Selektor S.L., Sokolov M.N., Solovieva S.E., Stoikov I.I., Stuzhin P.A., Suslov E.V., Ushakov E.N., Fedin V.P., Fedorenko S.V., Fedorova O.A., Fedorov Yu.V., Chvalun S.N., Tsivadze A.Yu., Shtykov S.N., Shurpik D.N., Shcherbina M.A., Yakimova L.S. // Russ. Chem. Rev. 2021. Vol. 90. N 8. P. 895. doi: 10.1070/RCR5011
  3. Manchineella S., Govindaraju T. // ChemPlusChem. 2017. Vol. 82. P. 88. doi: 10.1002/cplu.201600450
  4. Zhu X., Su H., Liu H., Sun B. // Anal. Chim. Acta. 2023. Vol. 1255. Article ID 341124. doi: 10.1016/j.aca.2023.341124
  5. Tao K., Xue B., Li Q., Hu W., Shimon L.J.W., Makam P., Si M., Yan X., Zhang M., Cao Y., Yang R., Li J., Gazit E. // Mater Today. 2019. Vol. 30. P. 10. doi: 10.1016/j.mattod.2019.04.002
  6. Wang Y.-M., Zeng Q., He L., Yin P., Sun Y., Hu W., Yang R. // iScience. 2021. Vol. 24. Article ID 102274. doi: 10.1016/j.isci.2021.102274
  7. Yang M., Yuan C., Shen G., Chang R., Xing R., Yan X. // J. Colloid Interface Sci. 2019. Vol. 557. P. 458. doi: 10.1016/j.jcis.2019.09.049
  8. Yang M., Xing R., Shen G., Yuan C., Yan X. // Colloids Surf. (A). 2019. Vol. 572. P. 259. doi: 10.1016/j.colsurfa.2019.04.020
  9. Chen Y., Tao K., Ji W., Makam P., Rencus-Lazar S., Gazit E. // Protein Peptide Lett. 2020. Vol. 27. P. 688. doi: 10.2174/0929866527666200212123542
  10. Tao K., Hu W., Xue B., Chovan D., Brown N., Shimon L.J.W., Maraba O., Cao Y., Tofail S.A.M., Thompson D., Li J., Yang R., Gazit E. // Adv. Mater. 2019. Vol. 31. P. 1807481. doi: 10.1002/adma.201807481
  11. Tao K., Fan Z., Sun L., Makam P., Tian Z., Ruegsegger M., Shaham-Niv S., Hansford D., Aizen R., Pan Z., Galster S., Ma J., Yuan F., Si M., Qu S., Zhang M., Gazit E., Li J. // Nat. Commun. 2018. Vol. 9. Article ID 3217. doi: 10.1038/s41467-018-05568-9
  12. Kleinsmann A.J., Nachtsheim B.J. // Org. Biomol. Chem. 2020. Vol. 18. P. 102. doi: 10.1039/C9OB02198A
  13. Santos D., Baptista R.M.F., Handa A., Almeida B., Rodrigues P.V., Torres A.R., Machado A., Belsley M., de Matos Gomes E. // Materials. 2023. Vol. 16. Article ID 2477. doi: 10.3390/ma16062477
  14. Safiullina A.S., Ziganshina S.A., Lyadov N.M., Klimovitskii A.E., Ziganshin M.A., Gorbatchuk V.V. // Soft Matter. 2019. Vol. 15. P. 3595. doi: 10.1039/c9sm00465c.
  15. Scarel M., Marchesan S. // Molecules. 2021. Vol. 26. Article ID 3376. doi: 10.3390/molecules26113376.
  16. Karanam G., Arumugam M. K. // Mol. Biol. Rep. 2020. Vol. 47. N 5. P. 3347. doi: 10.1007/s11033-020-05407-5
  17. Zhang H.-H., Yu W.-Y., Li L., Wu F., Chen Q., Yang Y., Yu C.-H. // J. Ethnopharmacol. 2018. Vol. 215. P. 156. doi: 10.1016/j.jep.2018.01.005
  18. Ye G., Huang C., Li J., Chen T., Tang J., Liu W., Long Y. // Mar. Drugs. 2021. Vol. 19. N 7. Article ID 402. doi: 10.3390/md19070402.
  19. Poonia B.K., Sidhu A., Sharma A.B. // J. Agr. Food Chem. 2022. Vol. 70. N 7. P. 2160. doi: 10.1021/acs.jafc.1c07659
  20. Winyakul C., Phutdhawong W., Tamdee P., Sirirak J., Taechowisan T., Phutdhawong W.S. // Molecules. 2022. Vol. 27. N 13. Article ID 4200. doi: 10.3390/molecules27134200
  21. Song Z., Hou Y., Yang Q., Li X., Wu S. // Mar. Drugs, 2021. Vol. 19. N 8. Article ID 403. doi: 10.3390/md19080403
  22. Kumar N., Mohandas C., Nambisan B., Kumar D.R.S., Lankalapalli R.S. // World J. Microbiol. Biotechnol. 2013. Vol. 29. P. 355. doi: 10.1007/s11274-012-1189-9
  23. Borthwick D. // Chem. Rev. 2012. Vol. 112. P. 3641. doi.org/10.1021/cr200398y
  24. Kurbasic M., Semeraro S., Garcia A.M., Kralj S., Parisi E., Deganutti C., De Zorzi R., Marchesan S. // Synthesis. 2019. Vol. 51. P. 2839. doi: 10.1055/s-0037-1612376
  25. Basiuk V.A., Gromovoy T.Y., Chuiko A.A., Soloshonok V.A., Kukhar V.P. // Synthesis. 1992. Vol. 05. P. 449. doi: 10.1055/s-1992-26131
  26. Ziganshin M.A., Safiullina A.S., Gerasimov A.V., Ziganshina S.A., Klimovitskii A.E., Khayarov K.R., Gorbatchuk V.V. // J. Phys. Chem. (B). 2017. Vol. 121. P. 8603. doi: 10.1021/acs.jpcb.7b06759
  27. Smith J., Ali F.I., Soldatov D.V. // CrstEngComm. 2014. Vol. 16. P. 7196. doi: 10.1039/c4ce00630e
  28. Pérez-Mellor A., Le Barbu-Debus K., Zehnacker A. // Chirality. 2020. Vol. 32. P. 693. doi: 10.1002/chir.23195
  29. Ziganshin M.A., Gerasimov A.V., Ziganshina S.A., Gubina N.S., Abdullina G.R., Klimovitskii A.E. // J. Therm. Anal. Calorim. 2016. Vol. 125. P. 905. doi: 10.1007/s10973-016-5458-y
  30. Ziganshin M.A., Larionov R.A., Gerasimov A.V., Ziganshina S.A., Klimovitskii A.E., Khayarov K.R., Mukhametzyanov T.A., Gorbatchuk V.V. // J. Pept. Sci. 2019. Vol. 25. Article ID e3177. doi: 10.1002/psc.3177
  31. Safiullina A.S., Buzyurov A.V., Ziganshina S.A., Gerasimov A.V., Schick C., Gorbatchuk V.V., Ziganshin M.A. // Thermochim. Acta. 2020. Vol. 692. Article ID 178748. doi: 10.1016/j.tca.2020.178748
  32. Carlini L., Chiarinelli J., Mattioli G., Castrovilli M.C., Valentini V., De Stefanis A., Bauer E.M., Bolognesi P., Avaldi L. // J. Phys. Chem. (B). 2022. Vol. 126. N 16. P. 2968. doi: 10.1021/acs.jpcb.1c10736
  33. Ларионов Р.А., Ахметшин Ш.Р., Герасимов А.В., Морозова А.С., Зиганшина С.А., Хаяров Х.Р., Горбачук В.В., Зиганшин М.А. // ЖОpХ. 2022. Т. 58. Вып. 8. С. 787. doi: 10.31857/S051474922208002X
  34. Larionov R.A., Akhmetshin S.R., Gerasimov A.V., Morozova A.S., Ziganshina S.A., Khayarov K.R., Gorbatchuk V.V., Ziganshin M.A. // Russ. J. Org. Chem. 2022. Vol. 58. N 8. P. 1076. doi: 10.1134/S1070428022080024
  35. Do H.T., Chua Y.Z., Habicht J., Klinksiek M., Hallermann M., Zaitsau D., Schick C., Held C. // RSC Adv. 2019. Vol. 9. P. 32722. doi: 10.1039/C9RA05730G
  36. Görbitz C.H. // Chem. Eur. J. 2007. Vol. 13. P.1022. doi: 10.1002/chem.200601427
  37. Ziganshin M.A., Gerasimov A.V., Gorbatchuk V.V., Gubaidullin A.T. // J. Therm. Anal. Calorim. 2015. Vol. 119. P. 1811. doi: 10.1007/s10973-014-4279-0
  38. Perov I.A., Ziganshina S.A., Larionov R.A., Gerasimov A.V., Gorbatchuk V.V., Ziganshin M.A. // Thermochimica Acta. 2021. V.700. Article ID 178937. doi: 10.1016/j.tca.2021.178937.
  39. Ye F., Cai M.H., Chen B., Xiao W., Li X.W., Guo, Y.W. // Chem. Nat. Compd. Vol. 54. P. 821. doi: 10.1007/s10600-018-2488-7
  40. Bellamy L.J. The Infra-red Spectra of Complex Molecules. New York: Wiley, 1975. doi: 10.1007/978-94-011-6017-9
  41. Akhmetshin S.R., Larionov R.A., Klimovitskii A.E., Skvortsova P.V., Akhmadiyarov A.A., Ziganshina S.A., Gorbatchuk V.V., Ziganshin M.A. // J. Mol. Liq. 2023. Vol. 387. Article ID 122613. doi: 10.1016/j.molliq.2023.122613
  42. Vyazovkin S., Burnham A.K., Criado J.M., Pérez-Maqueda L.A., Popescu C., Sbirrazzuoli N. // Thermochim Acta. 2011. Vol. 520. P. 1. doi: 10.1016/j.tca.2011.03.034
  43. Vyazovkin S., Chrissafis K., Di Lorenzo M.R., Koga N., Pijolat M., Roduit B., Sbirrazzuoli N., Suñol J.J. // Thermochim Acta. 2014. Vol. 590. P. 1. doi: 10.1016/j.tca.2014.05.036
  44. Friedman H.L. // J. Polym. Sci. (A). 1964. Vol. 6. P. 183. doi: 10.1002/polc.5070060121
  45. Ozawa T. // Bull. Chem. Soc. Japan. 1965. Vol. 38. P.1881. doi: 10.1246/bcsj.38.1881
  46. Ozawa T. // Thermochim Acta. 1992. Vol. 203. P. 159. doi: 10.1016/0040-6031(92)85192-X
  47. Flynn J.H., Wall L.A. // J. Res. Natl. Bur. Stand. 1966. Vol. 70. P. 478. doi: 10.6028/jres.070A.043
  48. Logvinenko V.A., Dybtsev D.N., Bolotov V.A., Fedin V.P. // J. Therm. Anal. Calorim. 2015. Vol. 121. P. 491. doi: 10.1007/s10973-015-4430-6

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML
Baixar

Declaração de direitos autorais © Russian Academy of Sciences, 2023