Complexation of peptides with crown ethers. Part 2. Thermokinetic behaviour of hydrated compounds consisting of α-amino acids, peptides and 18-crown-6

Kulikov, Oleg V.; Zielenkiewicz, W.; Utzig, E.

doi:10.1016/0040-6031(94)80191-6

Thermochimica Acta

1994

DOI: 10.1016/0040-6031(94)80191-6

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Complexation of peptides with crown ethers. Part 2. Thermokinetic behaviour of hydrated compounds consisting of α-amino acids, peptides and 18-crown-6

Oleg V. Kulikov

W. Zielenkiewicz

E. Utzig

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Cited by 4 publications

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“…For this reason, we suggest that the complexes of 18-crown-6 with the mentioned amino acids are impossible to crystallize from aqueous solutions under our experimental conditions. Note that 18-crown-6 forms with glycine and alanine weaker complexes than with the corresponding dipeptides formed by these amino acids (the decomposition temperatures of the latter complexes are 171 and 161oC, respectively [4,15]). Peptides can form intermolecular hydrogen bonds.…”

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Thermal dissociation of supramolecular complexes on the basis of 18-crown-6 and amino acids

2004

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The possibility of isolation of crystalline supramolecular complexes of 18-crown-6 with glycine, L-alanine, L-valine, L-leucine, L-phenylalanine, L-proline, L-hystidine, and L-threonine from aqueous solutions was studied. Comparative analysis of thermal decomposition of the complexes and their individual components and mechanical mixture was studied by means of thermogravimetry, differential thermal analysis, and differential scanning calorimetry. Crystaline complexes of 18-crown-6 with glycine, L-alanine, and L-hystidine were isolated and shown to be stable up to 140oC, which was additionally confirmed by IR spectroscopy.Synthetic macrocyclic compounds, crown ethers, have certain common features with antibiotics and enzymes [1]. Their interactions with biologically active compounds are important to study for modeling many biochemical processes and for preparing new polyfunctional biomaterials.The present research is a continuation of the series of works [2,3] where made use of solution calorimetry to reveal formation of 1 : 1 complexes between 18-crown-6 and a broad range of amino acids and peptides in aqueous solutions at 298 K. In this connection we set ourselves the aim to isolate the new supramolecular complexes in the crystal state and to study their properties.As shown in [4,5], crystalline complexes of 18-crown-6 with zwitter-ionic peptides are formed due to hydrogen bonds and electrostatic forces and have a lamellar structure comprising alternating polar and nonpolar areas. Separate molecules of the complexes are cross-linked with each other by hydrogen bonds between peptide groups, as well as via water molecules, thus forming high-polarity areas.18-Crown-6 molecules locate in low-polarity areas. Thus, like molecular complexes of peptides with crown ethers, complexes of 18-crown-6 with amino acids can form a basis for design of not only new biomaterials, but also of a new class of molecular conductors.Thermal decomposition of crystalline complexes of 18-crown-6 with amino acids was studied by thermogravimetry, differential thermal analysis (DTA), and differential scanning calorimetry (DSC).The resulting data were compared with respective data for crystalline components of the complexes and their mechanical mixtures at temperatures of up to 360oC. Of a-L-amino acids we took glycine (Gly), alanine (Ala), leucine (Leu), valine (Val), phenylalanine (Phe), proline (Pro), hystidine (His), and threonine (Thr). Table 1 lists the characteristics of thermal decomposition of the systems studied. The figure exemplifies certain thermal decomposition curves of individual components, mechanical mixtures, and complexes.As seen from the figure, 18-crown-6 characteristically gives two peaks. The first corresponds to melting (endo effect) in the 37340oC range and the second, to thermal decomposition (exo effect) in the 1753260oC range, with a weight loss of 90%. The product of the incomplete decomposition of 18-crown-6 below 300oC is a solid tarry brown substance. As shown in [6], thermal oxidation of 18-crown-6 occurs at ...

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Thermal dissociation of supramolecular complexes on the basis of 18-crown-6 and amino acids

2004

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Thermolysis of calix[4]resorcinarene complexes with secondary and tertiary amines

Utzig

Pietraszkiewicz

2004

Journal of Thermal Analysis and Calorimetry

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Thermal analysis of calix[4]resorcinarene complexes with secondary and tertiary amines

Utzig

Pietraszkiewicz

2004

J Therm Anal Calorim

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Complexation of peptides with crown ethers. Part 2. Thermokinetic behaviour of hydrated compounds consisting of α-amino acids, peptides and 18-crown-6

Cited by 4 publications

References 10 publications

Thermal dissociation of supramolecular complexes on the basis of 18-crown-6 and amino acids

Thermal dissociation of supramolecular complexes on the basis of 18-crown-6 and amino acids

Thermolysis of calix[4]resorcinarene complexes with secondary and tertiary amines

Thermal analysis of calix[4]resorcinarene complexes with secondary and tertiary amines

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