Measurement and modelling solubility of amino acids and peptides in aqueous 2-propanol solutions

Tam, Hoang; Franke, Patrick T.; Volpert, Sophia; Klinksiek, Marcel; Thome, Max; Held, Christoph

doi:10.1039/d1cp00005e

Cited by 10 publications

(6 citation statements)

References 39 publications

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“…Model correlation is important for the solubility data of solids. Many models have been reported to correlate or predict the solubility data of solids. − In this work, the 5-FC solubility data is correlated by the famous modified Apelblat model, , λ h model, Jouyban–Acree model, , and CNIBS/R-K model …”

Section: Resultsmentioning

confidence: 99%

Solubility of 5-Fluorocytosine in Different Pure and Binary Mixed Solvents: Measurement, Model Correlation, Solvent Effect, and Preferential Solvation

Cong

Wang

et al. 2021

J. Chem. Eng. Data

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In this work, the phase equilibrium solubility of 5-fluorocytosine (5-FC) in dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), 1-butanol, acetonitrile, 1-propanol, 1,4-dioxane, acetone, ethyl acetate, 2-propanol, 2-butanone, and mixture systems (DMSO + 2-propanol and DMF + 2-propanol) at a series of temperatures (283.15–323.15 K) is determined, and model correlation, solvent effect, and preferential solvation analysis are researched. The solubility of 5-FC is related to temperature, which decreases with decreasing temperature. For monosolvent systems, the mole solubility order is DMSO > DMF > 1-butanol > 1-propanol > 2-propanol > acetone > 2-butanone > 1,4-dioxane > acetonitrile > ethyl acetate. The solvent effect has been studied in monosolvents, hydrogen-bonding acceptor (HBA) interactions and nonspecific dipolarity/polarizability interactions favor dissolution, and solvent self-cohesiveness is not beneficial to dissolution. For two mixture systems, the mole solubility of 5-FC in DMSO + 2-propanol solvent systems is higher than that in DMF + 2-propanol solvent systems. A dimensionless parameter (δ) is defined to observe the deviation from ideality of mixed solvents whose values are all greater than zero. The equilibrium constant of the solvent exchange process (K ps) can be used to evaluate the preferential solvation of 5-FC. DMSO or DMF dissolves 5-FC in the local region around 5-FC preferentially. The equilibrium solubility data is correlated by four correlation models (modified Apelblat, λh, CNIBS/R-K, and Jouyban–Acree models). The greatest relative average deviation (RAD) and root-mean-square deviation (RMSD) values are 2.01% and 11.87 × 10–5 in pure solvent systems and 2.20% and 5.99 × 10–5 in mixture systems, respectively. These four models show excellent correlation with the experimental solubility data.

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Section: Resultsmentioning

confidence: 99%

Solubility of 5-Fluorocytosine in Different Pure and Binary Mixed Solvents: Measurement, Model Correlation, Solvent Effect, and Preferential Solvation

Cong

Wang

et al. 2021

J. Chem. Eng. Data

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“…Δ C p ( T m ) was applied in this work with the assumption on temperature independence of Δ C p . The activity coefficient of the solute in the solution was calculated by the PC-SAFT EoS, which has shown superior performance on the modeling solubility of drug-like molecules with medium sizes. , A fundamental description on the PC-SAFT can be found in the work of Gross and Sadowski . Due to the complexity of the PC-SAFT calculations, equation details on activity coefficients are not provided in this section to avoid distraction.…”

Section: Thermodynamic Modelsmentioning

confidence: 99%

Solubility Measurement and Modeling of 5-Methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile (Y Form) in Pure and Binary Solvents

2023

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5-Methyl-2-[(2-nitrophenyl) amino]-3-thiophenecarbonitrile, known as ROY for its red, orange, and yellow crystal colors, has attracted great attention for its rich polymorphism and has been widely adopted as a benchmark compound in crystallization studies. Form Y of ROY is the most stable polymorph at low temperature. Solubility of form Y in six pure solvents (methanol, ethanol, ethyl acetate, acetic acid, acetone, and DMSO) at different temperatures within a range of 292.15 to 334.15 K as well as in four organic (methanol, ethanol, acetone, DMSO) aqueous binary mixtures at different solvent compositions and a temperature of 301.15 K were determined via a UV spectrophotometric method. The experimental solubility data were modeled applying a state-of-the-art semi-predictive model: the PC-SAFT equation-of-state. Both the measured data and the proposed modeling tool could further facilitate studies on solvent screening and polymorphic control for the solution crystallization of ROY.

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“…8 Only 3 years later, Matsuo and Sawamura measured the solubility of L-leucine in water at 298.15 K. 9 After that, its solubility in water (298.15 K) was measured by Klussmann et al 10 Soon after, Bowden et al reported the ethanol solubility of L-leucine in 2018. 11 In addition, the solubility data in water and aqueous 2-propanol were determined by Do et al 12,13 Recently, the L-leucine solubility in water was measured by Aliyeva et al in 2022. 14 The mass fraction purity and the analysis methods were both provided by the suppliers.…”

Section: Introductionmentioning

confidence: 99%

Solubility Behavior, Hansen Solubility Parameters, and Thermodynamic Modeling of l-Leucine in 12 Monosolvents from 283.15 to 323.15 K

Wang,

Li,

Liu

et al. 2023

J. Chem. Eng. Data

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The solubility and solvent effects of L-leucine in monosolvent systems (water, methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, acetonitrile, 1,4-dioxane, acetone, methyl acetate, and ethyl acetate) were investigated by the static gravimetric method in the temperature range from 283.15 to 323.15 K (with 5 K intervals). The solubility increased expectedly with the increase in temperature in all solvents. The solubility order of L-leucine in monosolvents was ranked as water > methanol > ethyl acetate > isopropanol > methyl acetate > isobutanol > ethanol > n-propanol > acetone >1,4-dioxane > acetonitrile > n-butanol. The polymorph of L-leucine was investigated by powder X-ray diffraction. Experiments confirmed that the crystal form did not change during the determination of solubility. The solubility of L-leucine in 12 monosolvents was analyzed by Dimroth and Reichardt's polarity parameters [E T (30)], hydrogen bonds, cohesive energy density, molecular structures, viscosity, and Hansen solubility parameters. Solubility in these monosolvents was well correlated by the modified Apelblat model and the Yaws model. According to the Akaike information criterion and Akaike weight analysis, the modified Apelblat model achieves relatively better fitting results..

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Measurement and modelling solubility of amino acids and peptides in aqueous 2-propanol solutions

Abstract: Amino acids and peptides are essential components in the biochemical industry. The final products find use in a vast field of applications, are often synthesized by fermentation and purified in...

Cited by 10 publications

References 39 publications

Solubility of 5-Fluorocytosine in Different Pure and Binary Mixed Solvents: Measurement, Model Correlation, Solvent Effect, and Preferential Solvation

Solubility of 5-Fluorocytosine in Different Pure and Binary Mixed Solvents: Measurement, Model Correlation, Solvent Effect, and Preferential Solvation

Solubility Measurement and Modeling of 5-Methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile (Y Form) in Pure and Binary Solvents

Solubility Behavior, Hansen Solubility Parameters, and Thermodynamic Modeling of l-Leucine in 12 Monosolvents from 283.15 to 323.15 K

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