Solubility of Fmoc-d-tryptophan in twelve mono-solvents: Solvent effects analysis, molecular simulation, model correlation and comparison with structurally similar substances

IF 5.3 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Liquids Pub Date : 2025-04-14 DOI:10.1016/j.molliq.2025.127553

Long Zhao , Benbo Zhu , Junjie Li , Min Ding , Yusheng Xiao , Peng Wang , Bingbing Li

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Abstract

Fmoc-d-tryptophan, a derivative of tryptophan, is a widely used compound in biochemistry and drug discovery. Consequently, it was necessary to study the solubility of Fmoc-d-tryptophan in single solvents to fill the gap of the database. The solubility of Fmoc-d-tryptophan in twelve mono-solvents (methanol, ethanol, n-propanol, n-butanol, isopropanol, isobutanol, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, acetone, acetonitrile) was determined using the static gravimetric method over the temperature range of 283.15 K–323.15 K. In all solvents the Fmoc-d-tryptophan solubility increased with increasing temperature. The internal interactions of Fmoc-d-tryptophan were elucidated through the utilization of molecular simulations incorporating molecular electrostatic potential surfaces (MEPs) and interaction energy calculations. It was established that the solvation behavior is predominantly influenced by solvent polarity (E_T(30)) and hydrogen bonding, with additional factors such as the cohesion energy density exerting a contributory effect. The relationship between the solubility of different substances with similar structure in the same solvent is then discussed by comparing the solubility behavior of d-tryptophan, l-tryptophan and Fmoc-d-tryptophan. Furthermore, four models (Modified Apeblat, NRTL, Margules and UNIQUAC) were employed to fit the solubility data, with the Modified Apeblat model offering the most accurate representation.

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fmoc -d-色氨酸在12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 -d-色氨酸是色氨酸的衍生物，是生物化学和药物开发中广泛使用的化合物。因此，有必要研究fmoc -d-色氨酸在单一溶剂中的溶解度，以填补数据库的空白。用静态重量法测定了fmoc -d-色氨酸在12种单溶剂（甲醇、乙醇、正丙醇、正丁醇、异丙醇、异丁醇、乙酸甲酯、乙酸乙酯、乙酸丙酯、乙酸丁酯、丙酮、乙腈）中的溶解度，温度范围为283.15 K - 323.15 K。在所有溶剂中，fmoc -d-色氨酸的溶解度随温度升高而升高。通过结合分子静电势面（MEPs）和相互作用能计算的分子模拟，阐明了fmoc -d-色氨酸的内部相互作用。结果表明，溶剂化行为主要受溶剂极性（ET(30)）和氢键的影响，其他因素如内聚能密度也有影响。通过比较d-色氨酸、l-色氨酸和fmoc -d-色氨酸的溶解度，讨论了结构相似的不同物质在同一溶剂中的溶解度关系。采用4种模型（Modified Apeblat、NRTL、Margules和UNIQUAC）拟合溶解度数据，其中以Modified Apeblat模型最能准确表征溶解度数据。

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来源期刊

Journal of Molecular Liquids 化学-物理：原子、分子和化学物理

CiteScore

10.30

自引率

16.70%

发文量

2597

审稿时长

78 days

期刊介绍： The journal includes papers in the following areas: – Simple organic liquids and mixtures – Ionic liquids – Surfactant solutions (including micelles and vesicles) and liquid interfaces – Colloidal solutions and nanoparticles – Thermotropic and lyotropic liquid crystals – Ferrofluids – Water, aqueous solutions and other hydrogen-bonded liquids – Lubricants, polymer solutions and melts – Molten metals and salts – Phase transitions and critical phenomena in liquids and confined fluids – Self assembly in complex liquids.– Biomolecules in solution The emphasis is on the molecular (or microscopic) understanding of particular liquids or liquid systems, especially concerning structure, dynamics and intermolecular forces. The experimental techniques used may include: – Conventional spectroscopy (mid-IR and far-IR, Raman, NMR, etc.) – Non-linear optics and time resolved spectroscopy (psec, fsec, asec, ISRS, etc.) – Light scattering (Rayleigh, Brillouin, PCS, etc.) – Dielectric relaxation – X-ray and neutron scattering and diffraction. Experimental studies, computer simulations (MD or MC) and analytical theory will be considered for publication; papers just reporting experimental results that do not contribute to the understanding of the fundamentals of molecular and ionic liquids will not be accepted. Only papers of a non-routine nature and advancing the field will be considered for publication.