Direct Measurement of the Thermodynamics of Chiral Recognition in Bile Salt Micelles

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• 作者：Shauna L. Anderson ; David Rovnyak and Timothy G. Strein
• 关键词：amphiphiles ; analytical ; chiral resolution ; hydrophobic effect ; thermodynamics ; isothermal titration calorimetry ; bile salt ; micelle
• 刊名：Chirality
• 出版年：2016
• 出版时间：April 2016
• 年：2016
• 卷：28
• 期：4
• 页码：290-298
• 全文大小：1041K
• ISSN：1520-636X

文摘

Isothermal titration calorimetry (ITC) is shown to be a sensitive reporter of bile salt micellization and chiral recognition. Detailed ITC characterization of bile micelle formation as well as the chiral recognition capabilities of sodium cholate (NaC), deoxycholate (NaDC), and taurodeoxycholate (NaTDC) micelle systems are reported. The ΔH_demic of these bile salt micelle systems is directly observable and is strongly temperature-dependent, allowing also for the determination of ΔCp_demic. Using the pseudo-phase separation model, ΔG_demic and TΔS_demic were also calculated. Chirally selective guest–host binding of model racemic compounds 1,1’-bi-2-napthol (BN) and 1,1’-binaphthyl-2,2’-diylhydrogenphosphate (BNDHP) to bile salt micelles was then investigated. The S-isomer was shown to bind more tightly to the bile salt micelles in all cases. A model was developed that allows for the quantitative determination of the enthalpic difference in binding affinity that corresponds to chiral selectivity, which is on the order of 1 kJ mol^-1. Chirality 28:290–298, 2016.