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2nd ed. (the “Gold Book”). Oxford: Blackwell Scientific Publications, 1997. org/. Accessed June 2009. 2. Morris DC. Stereochemistry. New York: Wiley-Interscience/Royal Society of Chemistry, 2002. 3. Carrey FA, Sundberg RJ. Advanced Organic Chemistry. Part A: Structure and Mechanism. New York: Springer, 2007. 4. Wainer IW, Marcotte AA. Stereochemical terms and concepts, an overview. In: Wainer IW, ed. Drug Stereochemistry: Analytical Methods and Pharmacology. 2nd ed. , 1993. 5. Vargek M, Freedman TB, Lee E, et al.

The nature of chiral recognition: is it a three-point interaction? Chirality 1997; 9:99–102. 3d] [12/3/012/22:6:30] [30–47] 3 Molecular basis of chiral recognition Krzysztof Jo´z´wiak INTRODUCTION Two enantiomers of a chiral substance have all their main physicochemical properties the same. Three-dimensional (3D) structures of enantiomers are nearly identical; the only difference lies in the fact that two molecules are related to each other as mirror images. Molecules are dissymmetric and any differences in the properties of enantiomers may be expressed in unequal interactions with a dissymmetric environment.

8, where the order of substituent is L (large), M (medium), S (small), and S’ (smallest). The molecule is oriented in such a manner that the smallest (S’) substituent is directed away from the viewer. 8 The Cahn-Ingold-Prelog sequence rule, where L is the largest group attached to the chiral center, followed in size by M, S, and S0 . rotation. A center of chirality with clockwise rotation is specified as R, whereas the counterclockwise sense of rotation designates the S description of the stereocenter.

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