ABSTRACT

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. Such interactions are particularly an issue in biological systems where biomacromolecules (polypeptides, polynucleotides, sugars, etc.) are asymmetric and can disproportionately recognize enantiomers of a chiral substance. Molecular mechanism of such chiral recognition processes is a matter that has drawn researchers’ attention right from the earliest studies of stereochemistry. Recently, with the emergence of many new structural and computational techniques that may be employed in these studies, much more is known about the molecular basis of interactions between chiral molecules and (selector) macromolecules that lead to resolution. The purpose of this chapter is to present the introduction to various models describing molecular chiral recognition mechanisms and to overview several techniques that assist in deciphering these processes.