Drug stereochemistry: analytical methods and pharmacology by Irving W Wainer

By Irving W Wainer

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The free-energy differences D(DG8) were computed from the separation factors using Eq. 2. It was found that the distribution of separation factors (a) followed a power law (P(a) ¼ leÀl), which corresponded to an exponential decay for the chiral free-energy differences. A string model for enantiorecognition (SMED) was proposed in this paper to explain this observation on the basis of an extended Ogston three-point interaction model. Partially overlapping molecular interaction domains were analyzed in terms of a string-complementarity model for ligand-receptor complementarity.

3d] [12/3/012/22:6:30] [30–47] MOLECULAR BASIS OF CHIRAL RECOGNITION 37 point locations fixed in 3D space. On the other hand, both a macromolecule and ligand molecule(s) undergo conformational changes upon binding and the dynamics of this process plays a role in enantiorecognition. Such aspects were elegantly illustrated in 1991 by Sokolov and Zefirov in the so-called rocking tetrahedron model (14). The model proposed a dynamic explanation to the enzymatic reaction, which, in contrast to the Ogston reaction model, may be not only fully but also partially stereospecific.

27), who studied temperature dependence of chromatographic retention of enantiomers of 5-HT4 selective agonist, mosapride, on a Chiral-AGP column. The authors observed that van’t Hoff plots for enantiomers were highly dependent on pH of the mobile phase used in the experiment. 0 where two regression lines for two enantiomers crossed at the point corresponding to 303 K; at this temperature no enantioselectivity was found. As a result, the reversal of enantiomers’ elution order was shown for this pH: in temperature lower than 308C (R)-mosapride was eluted before the (S)-enantiomer, while in higher temperature the (S)-mosapride was eluted first.

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