手性二元醇及α-氨基酸焓对相互作用的溶剂效应
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摘要
手性选择过程在生命起源和进化的地球化学研究中已经成为一个中心课题。手性分子对映选择性相互作用,即手性识别的分子机制,在化学、生物、医药和材料等前沿研究领域也都是关键科学问题。而微量热法是研究溶液中溶质-溶质、溶质-溶剂非键弱相互作用(氢键,疏水键、盐键和范德华作用)能量效应的有效手段。本论文主要内容分为两部分:
第一部分,选取五种手性和两种非手性的脂肪族二元醇为研究对象,利用等温滴定微量热法(ITC)分别测定其在纯水及不同质量分数的DMSO-H_2O混合溶剂中的稀释焓,根据McMillan-Mayer理论计算得到七种二元醇的同系焓对作用系数(hXX),通过溶质-溶质以及溶质-溶剂相互作用对实验结果进行讨论分析。结果表明,ITC可以区分不同手性的焓对作用系数,这七种二元醇焓作用系数随w的变化主要取决于疏水-疏水、疏水-亲水、亲水-亲水相互作用之间的竞争平衡。
第二部分,选取L-脯氨酸和L-羟脯氨酸为研究对象,利用等温滴定微量热法分别测定其在纯水以及不同质量分数DMF-H_2O和DMSO-H_2O两种混合体系中的稀释焓,计算得到两种氨基酸的同系焓对作用系数,并讨论了两种溶剂的介入对焓对作用系数大小的影响。
Chiroselective process has become a central issue in the investigation of the origin of geochemistry and evolution of life. The molecular mechanism of chiral recognition is also a term which pervades a wide range of disciplines such as chemistry, biology, materials and pharmaceutics. For exploring weak nonbonding interactions in chiral molecular systems, the microcalorimetry is usually very useful. This paper consists of the following two parts:
The first part: Five chiral diols and two kinds of nonchiral diols were choosen as research objects. The dilution enthalpies of all of them in dimethylsulfoxide (DMSO) + water mixtures have been determined respectively, using an isothermal titration calorimeter (ITC) at 298.15 K. On the basis of the McMillan-Mayer theory, the homochiral enthalpic pairwise interaction coefficients (hXX) of the sevev diols in the DMSO + water mixtures of various mass fractions (w = 0 to 0.3) have been calculated. The results are discussed from the point of view of solute-solute interaction and solute-solvent interaction. It was found that the method of ITC can differentiate the energies of homochiral interactions hXX between different pairs of optical isomers in aqueous solutions. The variations of with w for the four diols depend largely on the competition equilibrium between hydrophobic-hydrophobic, hydrophilic-hydrophilic and hydrophobic-hydrophilic interactions in DMSO + water mixtures.
The second part: L-proline and L-hydroxyproline were choosen as research objects. By using Isothermal titration calorimetry (ITC), the enthalpies of dilution of the two amino acids in pure water and various mass fractions (w = 0 to 0.3) of DMSO-H_2O and DMF-H_2O mixtures have been determined. The enthalpic interaction coefficients have been calculated based on the statistical thermodynamics theory of McMillan-Mayer. The influence of solvent-mediated solute-solute interaction on the values of enthalpic interaction coefficients has been discussed.
第一部分,选取五种手性和两种非手性的脂肪族二元醇为研究对象,利用等温滴定微量热法(ITC)分别测定其在纯水及不同质量分数的DMSO-H_2O混合溶剂中的稀释焓,根据McMillan-Mayer理论计算得到七种二元醇的同系焓对作用系数(hXX),通过溶质-溶质以及溶质-溶剂相互作用对实验结果进行讨论分析。结果表明,ITC可以区分不同手性的焓对作用系数,这七种二元醇焓作用系数随w的变化主要取决于疏水-疏水、疏水-亲水、亲水-亲水相互作用之间的竞争平衡。
第二部分,选取L-脯氨酸和L-羟脯氨酸为研究对象,利用等温滴定微量热法分别测定其在纯水以及不同质量分数DMF-H_2O和DMSO-H_2O两种混合体系中的稀释焓,计算得到两种氨基酸的同系焓对作用系数,并讨论了两种溶剂的介入对焓对作用系数大小的影响。
Chiroselective process has become a central issue in the investigation of the origin of geochemistry and evolution of life. The molecular mechanism of chiral recognition is also a term which pervades a wide range of disciplines such as chemistry, biology, materials and pharmaceutics. For exploring weak nonbonding interactions in chiral molecular systems, the microcalorimetry is usually very useful. This paper consists of the following two parts:
The first part: Five chiral diols and two kinds of nonchiral diols were choosen as research objects. The dilution enthalpies of all of them in dimethylsulfoxide (DMSO) + water mixtures have been determined respectively, using an isothermal titration calorimeter (ITC) at 298.15 K. On the basis of the McMillan-Mayer theory, the homochiral enthalpic pairwise interaction coefficients (hXX) of the sevev diols in the DMSO + water mixtures of various mass fractions (w = 0 to 0.3) have been calculated. The results are discussed from the point of view of solute-solute interaction and solute-solvent interaction. It was found that the method of ITC can differentiate the energies of homochiral interactions hXX between different pairs of optical isomers in aqueous solutions. The variations of with w for the four diols depend largely on the competition equilibrium between hydrophobic-hydrophobic, hydrophilic-hydrophilic and hydrophobic-hydrophilic interactions in DMSO + water mixtures.
The second part: L-proline and L-hydroxyproline were choosen as research objects. By using Isothermal titration calorimetry (ITC), the enthalpies of dilution of the two amino acids in pure water and various mass fractions (w = 0 to 0.3) of DMSO-H_2O and DMF-H_2O mixtures have been determined. The enthalpic interaction coefficients have been calculated based on the statistical thermodynamics theory of McMillan-Mayer. The influence of solvent-mediated solute-solute interaction on the values of enthalpic interaction coefficients has been discussed.
引文
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