Thermochemical investigation of acid-base interactions in peptide solutions

Gorboletova, G. G.; Kochergina, L. A.

doi:10.1007/s10973-006-7679-y

Cited by 16 publications

(4 citation statements)

References 7 publications

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“…Ранее в результате изучения термодинамики реакций диссоциации с участием аминокислот и коротких пептидов нами были отмечены некоторые особенности. В работе [38] было высказано предположение, что в процессах ступенчатой ионизации какие-либо сольватационные изменения происходят в основном на функциональных группах этих соединений, так как суммарные значения rS ступенчатых реакций диссоциации дипептидов имеют близкие значения с суммой rS диссоциации карбоксильных и бетаиновых групп соответствующих аминокислот. Данное предположение нашло подтверждение при изучении термодинамики протолитических равновесий в растворах диглицина и триглицина.…”

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Theoretical and Experimental Approaches in the Study of Electrochemical and Thermodynamic Properties of Polyfunctional Organic Compounds in Liquid-Phase and Heterophase Systems

2023

Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.

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The publication reflects the experimental substantiation and fundamental development of some important ideas of the theory of the mutual influence of functional substitution in complex molecules of macrocyclic and chelating compounds on their coordination, solvation and redox properties, as well as the formation of algorithms for searching useful functions of these compounds. Researchers of the Analytical Chemistry Department of the Ivanovo State University of Chemistry and Technology have been studying the electrochemical and thermodynamic behavior of porphyrins, complexones, amino acids, peptides and the corresponding complexes with d- and f-metal ions, their influence on coordination, solvation and catalytic processes for a number of years. The results obtained together with the literature data are discussed in the review. For citation: Bazanov M.I., Berezina N.M., Gridchin S.N., Krutova O.N., Gorboletova G.G., Bychkova S.A., Lytkin A.I., Chernyavskaya N.V., Chernikov V.V., Volkov A.V. Theoretical and experimental approaches in the study of electrochemical and thermodynamic properties of polyfunctional organic compounds in liquid-phase and heterophase systems. ChemChemTech [Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.]. 2023. V. 66. N 7. P. 98-110. DOI: 10.6060/ivkkt.20236607. 6839j.

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Section: таблицаunclassified

Theoretical and Experimental Approaches in the Study of Electrochemical and Thermodynamic Properties of Polyfunctional Organic Compounds in Liquid-Phase and Heterophase Systems

2023

Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.

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“…The influence of the aqueous solution ionic strength on the heat effect of acid-base equilibrium involving dipeptides built of valine, alanine, glycine, serine, and asparagine have been analyzed earlier in [1][2][3][4][5][6][7][8][9][10], and standard thermodynamic parameters of the corresponding reactions (pK 0 , Δ r G 0 , Δ r H 0 , and Δ r S 0 ) have been determined.…”

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“…Standard thermodynamic parameters of dissociation of the studied dipeptides are collected in Table 2 [4] thus enhancing the interaction between the ammonium cation and the carboxylate anion. The enhancement of the interaction between the oppositely charged ions could also result in the changed distribution of the solvent molecules around the dipeptide molecule leading to a decrease in Δ dis S 0 of the carboxylic group and an increase in Δ dis S 0 of the betaine group due to the binding of more water Reaction pK 0 Δ dis G 0 , kJ/mol Δ dis Н 0 , kJ/mol -Δ dis S 0 , J mol -1 K -1…”

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“…Glycyl-L-asparagine [4] The introduction of further methylene groups into the glycine fragments of the dipeptides (along the glycylglycine-glycyl-β-alanine-β-alanylglycine, and β-alanyl-β-alanine series, Table 3) decreased the acidity of the corresponding carboxylic or betaine groups due to the enhanced inductive effect of the hydrocarbon moiety and led to the enhanced hydration of the dipeptide because of the increased distance between the positive and the negative charges.…”

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Thermodynamic parameters of protolytic equilibria of selected dipeptides in aqueous solutions

Gridchin

2015

Russ J Gen Chem

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Heat effects of stepwise dissociation of D,L-valyl-D,L-leucine, L-leucyl-L-leucine, D,Lleucylglycine, and glycyl-D,L-leucine (298.15 K; 0.1, 0.5, or 1.0 mol/L KNO 3 ) have been determined by direct calorimetry. Standard thermodynamic parameters of the studied equilibria have been calculated.The influence of the aqueous solution ionic strength on the heat effect of acid-base equilibrium involving dipeptides built of valine, alanine, glycine, serine, and asparagine have been analyzed earlier in [1-10], and standard thermodynamic parameters of the corresponding reactions (pK 0 , Δ r G 0 , Δ r H 0 , and Δ r S 0 ) have been determined.In this work we studied the dipeptides including leucine fragment: D,L-valyl-D,L-leucine, L-leucyl-Lleucine, D,L-leucylglycine, and glycyl-D,L-leucine. The constants of stepwise dissociation of their carboxylic and betaine groups were considerably different, thus allowing independent calorimetric determination of heat effects of reactions (1) and (2).The enthalpy of dissociation of H 2 L + and HL could be found as the difference between the mixing and the dilution enthalpies [Eq. (3)]:where Δ mix H being the enthalpy of mixing of HNO 3 solution with the dipeptide solution in the presence of the background electrolyte; Δ dil H being the enthalpy of dilution of the HNO 3 solution in the background electrolyte solution; α being the degree of protonation of HL and L -. Heat effects of dissociation of the studied dipeptides at 298.15 K in the presence of 0.1, 0.5, and 1.0 mol/L of KNO 3 are collected in Table 1.The values of Δ dis Н found for the set of ionic strengths allowed calculation of the standard thermodynamic parameters of the studied equilibria. In order to extrapolate the heat effects to zero ionic strength we used a one-parametric Eq. (4) [11]:where Δ dis Н and Δ dis Н 0 being the reaction enthalpies at the finite and zero ionic strength, respectively; b being an empirical coefficient; Δz 2 being a difference of charges of the reaction products and the starting reactants; and Ψ(I) being a theoretically derived function of ionic strength [11]. The corresponding thermodynamic parameters of the dipeptides dissociation constants were then calculated using the Vasilev equation (5) [11]: pK 0 = pK + AΔz 2 [I 1/2 /(1+1.6I 1/2 ) -0.05I] + 0.05I, (5) where K 0 and K being thermodynamic and concentration constants of dissociation, respectively, and A being a Debye-Huckel theory constant.Concentration constants of dissociation of D,Lvalyl-D,L-leucine, L-leucyl-L-leucine, D,L-leucylglycine, and glycyl-D,L-leucine have been earlier determined in [12][13][14][15]. Standard thermodynamic parameters of dissociation of the studied dipeptides are collected in Table 2 along with our results of similar calorimetry studies of a series of other dipeptides.The results of this work are in good agreement with the earlier suggestions on the dependence of thermo-

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Standard enthalpies of formation of the phenylalanine isomers and the products of their dissociation in aqueous solutions

Kochergina

Ratkova

Emeljanov

2008

J Therm Anal Calorim

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Thermochemical investigation of acid-base interactions in peptide solutions

Cited by 16 publications

References 7 publications

Theoretical and Experimental Approaches in the Study of Electrochemical and Thermodynamic Properties of Polyfunctional Organic Compounds in Liquid-Phase and Heterophase Systems

Theoretical and Experimental Approaches in the Study of Electrochemical and Thermodynamic Properties of Polyfunctional Organic Compounds in Liquid-Phase and Heterophase Systems

Thermodynamic parameters of protolytic equilibria of selected dipeptides in aqueous solutions

Standard enthalpies of formation of the phenylalanine isomers and the products of their dissociation in aqueous solutions

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