Drug stereochemistry: analytical methods and pharmacology by Irving W Wainer

By Irving W Wainer

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3d] [12/3/012/22:6:30] [30–47] 36 DRUG STEREOCHEMISTRY: ANALYTICAL METHODS AND PHARMACOLOGY essential for isocitrate dehydrogenase to distinguish between the two enantiomers. 3A and B. a, b, and c fragments occupy the same protein locations, the consequence of which is that the d fragment (a hydroxyl group) points into the opposite directions and interacts with different protein locations (Mg2þ or Arg119 residue for D- and L-enantiomer, respectively). The authors concluded that a similar “four-location model” is capable of explaining other stereoselective enzyme systems including mandelate racemase (10).

It was found, for example, that some agonists depending on their stereoconfiguration are able to preferentially activate different classes of G protein as a downstream effect of binding to the b2-adrenergic receptor (19). Further investigations revealed that two isomers can induce different protein conformations of the b2 receptor within the agonist binding site. 3d] [12/3/012/22:6:30] [30–47] 38 DRUG STEREOCHEMISTRY: ANALYTICAL METHODS AND PHARMACOLOGY that is further manifested as a significant difference in functional assays (reviewed in Ref.

The results suggested that chiral selection statistics may be interpreted in terms of more general concepts related to biomolecular recognition. In 1992, Berthod et al. proposed a purely empirical procedure to predict chromatographic enantioselectivity using a representation of the molecular structure of chiral analytes (34). The approach was based on the assumption that the difference in molecular free energy of the chiral interaction between two enantiomers (DDGc) can be broken down into four terms, each term being related to one of the four different substituents attached to the asymmetric carbon of the analyte: DDGc ¼ ðDGc11 À DGc12 Þ þ ðDGc21 À DGc22 Þ þ ðDGc31 À DGc32 Þ þ ðDGc41 À DGc42 Þ (6) Each substituent has its own contribution on the DDGc value, and in order to assess these impacts a cohort of 126 chiral compounds resolved on two chiral stationary phases (based on modified cyclodextrins) were analyzed.

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