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 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.

About the authors

R. A. Larionov

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

S. A. 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. E. Klimovitski

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

Kh. R. Khayarov

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

O. B. Babaeva

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

V. V. Gorbachuk

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

M. A. 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

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