Solubility of Fmoc-l-glutamic Acid in 14 Monosolvents: Solvent Effects Analysis, Molecular Simulation, Model Correlation, and Comparison with Structurally Similar Substances

IF 2.1 3区工程技术 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Chemical & Engineering Data Pub Date : 2025-09-19 DOI:10.1021/acs.jced.5c00424

Xiaodan Chen, , , Wei Gao, , , Tianqi Yu, , , Chen Ouyang, , , Hongcai Guo, , , Jintao Liu, , , Weikun Tang, , and , Peng Wang*,

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Abstract

Fmoc-l-glutamic acid, as a derivative of glutamic acid, exhibits prominent applicability in biochemical science and medicinal chemistry. In order to improve the relevant database, this study used the static gravimetric method to determine the solubility of Fmoc-l-glutamic acid in 14 single solvents (including methanol, ethanol, n-propanol, n-butanol, isopropanol, n-pentanol, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, dimethyl carbonate, acetone, 2-butanone, and acetonitrile) within the temperature range of 283.15–323.15 K. The experimental data reveal that the dissolution capability of Fmoc-l-glutamic acid is enhanced as the temperature rises in all investigated solvent systems. By combining molecular electrostatic potential surface (MEPS) analysis and interaction energy calculation, this work elucidated the intermolecular interaction mechanism of Fmoc-l-glutamic acid with solvents. Research has confirmed that solvent polarity (E_T(30)), hydrogen bonding, and cohesive energy density mainly affect the solvation behavior. In addition, the solubility of Fmoc-l-glutamic acid in 14 single solvents was evaluated using Hansen solubility parameters (HSPs) and interaction region indicator (IRI). By comparing the solubility behavior of Fmoc-l-glutamic acid and l-glutamic acid 5-methyl ester, the solubility of structurally similar substances in the same solvent was explored.

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fmoc -l-谷氨酸在14种单溶剂中的溶解度：溶剂效应分析、分子模拟、模型关联以及与结构相似物质的比较

fmoc -l-谷氨酸作为谷氨酸的衍生物，在生物化学和药物化学方面具有突出的适用性。为了完善相关数据库，本研究采用静态重量法测定了fmoc -l-谷氨酸在14种单一溶剂（甲醇、乙醇、正丙醇、正丁醇、异丙醇、正戊醇、乙酸甲酯、乙酸乙酯、乙酸丙酯、乙酸丁酯、碳酸二甲酯、丙酮、2-丁酮、乙腈）中的溶解度，温度范围为283.15 ~ 323.15 K。实验数据表明，在所有溶剂体系中，fmoc -l-谷氨酸的溶解能力都随着温度的升高而增强。结合分子静电势面（MEPS）分析和相互作用能计算，阐明了fmoc -l-谷氨酸与溶剂的分子间相互作用机理。研究证实溶剂极性（ET(30)）、氢键和内聚能密度是影响溶剂化行为的主要因素。此外，利用Hansen溶解度参数（HSPs）和相互作用区域指标（IRI）评价了fmoc -l-谷氨酸在14种单一溶剂中的溶解度。通过比较fmoc -l-谷氨酸和l-谷氨酸5-甲酯的溶解度行为，探讨了结构相似物质在同一溶剂中的溶解度。

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来源期刊

Journal of Chemical & Engineering Data 工程技术-工程：化工

CiteScore

5.20

自引率

19.20%

发文量

324

审稿时长

2.2 months

期刊介绍： The Journal of Chemical & Engineering Data is a monthly journal devoted to the publication of data obtained from both experiment and computation, which are viewed as complementary. It is the only American Chemical Society journal primarily concerned with articles containing data on the phase behavior and the physical, thermodynamic, and transport properties of well-defined materials, including complex mixtures of known compositions. While environmental and biological samples are of interest, their compositions must be known and reproducible. As a result, adsorption on natural product materials does not generally fit within the scope of Journal of Chemical & Engineering Data.