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Cyclization of L-Leucyl-L-valine Dipeptide in the Crystal Phase under Non-Isоthermal Conditions

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Abstract

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

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Funding

The work was carried out with the support of the Kazan (Volga region) Federal University within the framework of the strategic academic leadership program Priority-2030 (R.A. Larionov), at the expense of subsidy provided to the Kazan Federal University to fulfill the state assignment in the field of scientific activity (No. FZSM-2023- 0020, V.V. Gorbachuk, M.A. Ziganshin, and A.E. Klimovitsky) and the state assignment of the Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences” (O.B. Babaeva and S.A. Ziganshina).

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Authors and Affiliations

  1. A.M. Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University, 420008, Kazan, Russia

    R. A. Larionov, S. A. Ziganshina, A. E. Klimovitskii, Kh. R. Khayarov, V. V. Gorbachuk & M. A. Ziganshin

  2. E.K. Zavoisky Kazan Institute of Physics and Technology, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”, 420029, Kazan, Russia

    S. A. Ziganshina

  3. A.E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”, 420088, Kazan, Russia

    O. B. Babaeva

  4. cademy of Sciences of the Republic of Tatarstan, 420111, Kazan, Russia

    M. A. Ziganshin

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  1. R. A. Larionov
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  2. S. A. Ziganshina
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  3. A. E. Klimovitskii
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Correspondence to M. A. Ziganshin.

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M.A. Ziganshin is a member of the editorial board of the Journal of General Chemistry. The remaining authors declare that there is no conflict of interest.

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Larionov, R.A., Ziganshina, S.A., Klimovitskii, A.E. et al. Cyclization of L-Leucyl-L-valine Dipeptide in the Crystal Phase under Non-Isоthermal Conditions. Russ J Gen Chem 93, 2775–2784 (2023). https://doi.org/10.1134/S1070363223110063

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