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The interaction of lipoic acid with β-cyclodextrin (β-CD) has been studied by capillary electrophoresis in aqueous phosphate buffer (20 mM, pH = 9.0) at 20 °C. The results allowed us to detect the formation of an inclusion complex with a 1:1 lipoic acid/β-CD stoichiometry and an association constant of 1645 M−1. The geometry of the inclusion complex in D2O was investigated by means of 2D-ROESY (Rotating-frame Overhauser Enhancement Spectroscopy) NMR experiments, which showed the occurrence of a bimodal complexation of lipoic acid inside the β-CD cavity. Semi-empirical calculations using the PM3 method show that the orientations of the included lipoic acid are very close in energy, thus confirming the experimental observations. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
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Carofiglio et al. (2002) studied this question.
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