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Heat Capacities of L-Histidine, L-Phenylalanine, L-Proline, L-Tryptophan and L-Tyrosine

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Heat Capacities of L-Histidine, L-Phenylalanine, L-Proline, L-Tryptophan and L-Tyrosine molecules Article Heat Capacities of L-Histidine, L-Phenylalanine, L-Proline, L-Tryptophan and L-Tyrosine Václav Pokorný 1, VojtˇechŠtejfa 1 , Jakub Havlín 2, KvˇetoslavR ˚užiˇcka 1 and Michal Fulem 1,* 1 Department of Physical Chemistry, University of Chemistry and Technology Prague, Technická 5, 166 28 Prague 6, Czech Republic; [email protected] (V.P.); [email protected] (V.Š.); [email protected] (K.R.) 2 Central Laboratories, University of Chemistry and Technology Prague, Technická 5, 166 28 Prague 6, Czech Republic; [email protected] * Correspondence: [email protected] Abstract: In an effort to establish reliable thermodynamic data for proteinogenic amino acids, heat capacities for L-histidine (CAS RN: 71-00-1), L-phenylalanine (CAS RN: 63-91-2), L-proline (CAS RN: 147-85-3), L-tryptophan (CAS RN: 73-22-3), and L-tyrosine (CAS RN: 60-18-4) were measured over a wide temperature range. Prior to heat capacity measurements, thermogravimetric analysis was performed to determine the decomposition temperatures while X-ray powder diffraction (XRPD) and heat-flux differential scanning calorimetry (DSC) were used to identify the initial crystal structures and their possible transformations. Crystal heat capacities of all five amino acids were measured by Tian–Calvet calorimetry in the temperature interval from 262 to 358 K and by power compensation DSC in the temperature interval from 307 to 437 K. Experimental values determined in this work were then combined with the literature data obtained by adiabatic calorimetry. Low temperature heat capacities of L-histidine, for which no literature data were available, were determined in this work Citation: Pokorný, V.; Štejfa, V.; using the relaxation (heat pulse) calorimetry from 2 K. As a result, isobaric crystal heat capacities and Havlín, J.; R ˚užiˇcka,K.; Fulem, M. standard thermodynamic functions up to 430 K for all five crystalline amino acids were developed. Heat Capacities of L-Histidine, L-Phenylalanine, L-Proline, Keywords: L-histidine; L-phenylalanine; L-proline; L-tryptophan; L-tyrosine; crystal heat capacity; L-Tryptophan and L-Tyrosine. thermodynamic functions Molecules 2021, 26, 4298. https:// doi.org/10.3390/molecules26144298 Academic Editors: Vera L. S. Freitas 1. Introduction and Maria Ribeiro da Silva This work represents a continuation of our previous project [1–4], which aimed Received: 18 June 2021 to establish reliable thermodynamic data along the saturation curve for proteinogenic Accepted: 13 July 2021 amino acids. Despite their significance [5,6] and wide use, for example, in pharmaceutical Published: 15 July 2021 formulations as coformers used to increase the bioavailability of poorly water soluble drugs [7,8], there are still considerable gaps in the availability of fundamental thermody- Publisher’s Note: MDPI stays neutral namic data for basic amino acids [2,9,10]. In addition, the values for properties such as with regard to jurisdictional claims in sublimation or crystal-phase enthalpies of formation often show very poor interlaboratory published maps and institutional affil- agreement [2,10]. The discrepancies in sublimation thermodynamic properties can be iations. ascribed to the zwitterionic nature of amino acid crystals, which causes their extremely low volatility and renders the experimental determination of their sublimation pressure and enthalpy difficult, prone to systematic errors, or even unfeasible at room temper- ature using current available experimental techniques. Thermodynamically controlled Copyright: © 2021 by the authors. extrapolation [11] of sublimation pressures measured at higher temperatures therefore Licensee MDPI, Basel, Switzerland. seems to be the only method to obtain sublimation thermodynamic data for amino acids at This article is an open access article temperatures relevant to their biological activity. For the application of this method, several distributed under the terms and thermodynamically linked properties are necessary as inputs: (i) sublimation pressure, conditions of the Creative Commons which was determined at higher temperatures by the Knudsen effusion method for several Attribution (CC BY) license (https:// amino acids including L-proline (from 373 to 416 K) in our previous work [1] (the measure- creativecommons.org/licenses/by/ ments of other amino acids are in progress); (ii) heat capacity in the ideal gas state, which 4.0/). Molecules 2021, 26, 4298. https://doi.org/10.3390/molecules26144298 https://www.mdpi.com/journal/molecules Molecules 2021, 26, 4298 2 of 12 is typically calculated by the combination of quantum-chemical and statistical thermody- namics methods [3]; and (iii) experimental crystal heat capacities, which were measured in this work for L-histidine, L-phenylalanine, L-proline, L-tryptophan, and L-tyrosine in the temperature range overlapping with that of sublimation pressure measurements by the Knudsen effusion method. Simultaneous correlation of the above-mentioned properties also ensures their thermodynamic consistency. In order to establish a safe upper temperature limit for the heat capacity measurements, the decomposition temperatures of the amino acids studied were first determined by thermogravimetry. Consequently, after determining the initial crystal structure at 298.15 K by X-ray powder diffraction (XRPD), the phase behavior was studied in the temperature range from 183 K to the decomposition temperature of each amino acid using a heat flux differential scanning calorimeter (DSC) to detect possible phase transitions. Heat capacities in the temperature range from 262 to 358 K were determined with Tian–Calvet calorimetry and extended up to 437 K by using a power compensation DSC. Literature low-temperature heat capacities, which are determined by adiabatic calorimetry from about 10 K to 300 K, were found for all amino acids studied except L-histidine for which new measurements by means of thermal-relaxation calorimetry were performed in this work in the temperature range from 2 to 300 K. 2. Results and Discussion 2.1. Thermogravimetric Analysis (TGA) All studied amino acids decompose at/prior to melting using the usual temperature scanning rates (5 to 40) K·min−1. The samples were studied by TGA previously and the lit- erature temperatures of decomposition along with the results of this work are summarized in Table1. It should be noted that the decomposition kinetics is influenced by a number of factors (heating rate, sample size, purge gas, etc.). This is reflected by the relatively large range of reported decomposition temperatures. Despite that, thermograms of this work (shown in Figure1) agree qualitatively with the literature ones for L-histidine [12,13], L-proline [14], L-phenylalanine [15,16], L-tryptophan [16], and L-tyrosine [16]. The decomposition behavior of the amino acids studied exhibits various patterns. The simplest decomposition path can be observed in the case of L-tyrosine (Figure1e), which shows a simple one-stage decomposition. For L-histidine (Figure1a) and L-tryptophan (Figure1d), two decomposition phases can be clearly distinguished. The situation is more complicated in the case of L-phenylalanine (Figure1b) and L-proline (Figure1c). In both cases, four peaks can be observed on the heat flow curve (red), two of which are, however, quite small. In the case of L-proline, the first small peak at 484 K does not seem to be accompanied by any mass loss, pointing to a possible crystal–crystal transition. Note that the temperatures of fusion reported by Do et al. [17] (see Table1) are higher than those of decomposition by (20 to 100) K. In order to avoid decomposition, Do et al. [17] used scanning rates up to 20,000 K·s −1. Molecules 2021, 26, x FOR PEER REVIEW 3 of 13 Molecules 2021, 26, 4298 3 of 12 (a) (b) 0 100 endo 0 100 endo V V μ μ −20 80 −20 50 −40 Weight / % / % Weight Heat Flow / Heat Flow / −40 60 0 −60 L-Histidine L-Phenylalanine 300 400 500 600 700 300 400 500 600 700 T/K T/K (c) (d) endo 0 0 100 100 endo V V μ μ 80 −10 −20 50 60 −20 Weight / % Weight Weight / % −40 40 Heat Flow / Heat Flow / 0 −30 L-Proline 20 L-Tryptophan −60 300 400 500 600 300 400 500 600 700 T/K T/K (e) 100 0 endo V 80 μ −20 60 −40 Weight / % Weight 40 Heat Flow / −60 20 L-Tyrosine 300 400 500 600 700 T/K Figure 1. TGA analysis of (a) L-histidine, (b) L-phenylalanine, (c) L-proline, (d) L-tryptophan, and (e) L-tyrosine. Figure 1. TGA analysis of (a) L-histidine, (b) L-phenylalanine, (c) L-proline, (d) L-tryptophan, and (e) L-tyrosine. The decomposition behavior of the amino acids studied exhibits various patterns. The simplest decomposition path can be observed in the case of L-tyrosine (Figure 1e), which shows a simple one-stage decomposition. For L-histidine (Figure 1a) and L-trypto- phan (Figure 1d), two decomposition phases can be clearly distinguished. The situation is more complicated in the case of L-phenylalanine (Figure 1b) and L-proline (Figure 1c). In both cases, four peaks can be observed on the heat flow curve (red), two of which are, however, quite small. In the case of L-proline, the first small peak at 484 K does not seem to be accompanied by any mass loss, pointing to a possible crystal–crystal transition. Note that the temperatures of fusion reported by Do et al. [17] (see Table 1) are higher than those of decomposition by (20 to 100) K. In order to avoid decomposition, Do et al. [17] used scanning rates up to 20,000 K·s −1. Molecules 2021, 26, 4298 4 of 12 Table 1. Temperatures of fusion and decomposition of L-histidine, L-phenylalanine, L-proline, L-tryptophan, and L-tyrosine a. Reference Tdecomp, onset/K Tdecomp, peak top/K Method Scanning Rate, Purge Gas b L-histidine (two-stage decomposition) (Tfus = 619 ± 7 K ) SRC recommendation c 560 - - - Wesolowski and Erecinska [18] - 523 DTA 5 K min−1, air Wesolowski and Erecinska [18] - 528 DTG 5 K min−1, air Anandan et al.
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