Journal
CHIRALITY
Volume 28, Issue 4, Pages 290-298Publisher
WILEY
DOI: 10.1002/chir.22580
Keywords
amphiphiles; analytical; chiral resolution; hydrophobic effect; thermodynamics; isothermal titration calorimetry; bile salt; micelle
Funding
- National Science Foundation [CHE-1153052, CHE-1337721]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1153052, 1337721] Funding Source: National Science Foundation
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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 H-demic of these bile salt micelle systems is directly observable and is strongly temperature-dependent, allowing also for the determination of Cp-demic. Using the pseudo-phase separation model, G(demic) and TSdemic 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. (c) 2016 Wiley Periodicals, Inc.
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