Prostereoisomerism and biological activity: possible implications for drug design

Authors : SOSALE CHANDRASEKHAR

Pages : 535-545

View : 21 | Download : 10

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :Prostereoisomerism insert ignore into journalissuearticles values(PIM);, representing a subgroup within the achiral class of molecules, is manifested in a chiral environment. Although this is regardless of the orientation of the prostereoisomeric insert ignore into journalissuearticles values(PIC); molecule, PIM is manifested most emphatically in relation to a chiral surface insert ignore into journalissuearticles values(`two-dimensional chirality`);. Then PIM is tantamount to `de facto chirality` as attachment of the PIC molecule to the surface leads to diastereomeric possibilities insert ignore into journalissuearticles values(cf. Ogston`s hypothesis);. Furthermore, the formation of host--guest complexes requires a steric complementarity between the component molecules. The fact that the weak dispersive forces involved therein require an optimum distance implies a `snugness of fit` criterion. This further implies that a chiral host prefers a chiral guest molecule, and a chiral surface prefers a PIC molecule as substrate. These indicate a general stereochemical criterion for host--guest complexation that is particularly relevant to the case of biological receptors. Indeed, a survey of several known achiral drug molecules indicates that they generally possess at least one PIC moiety, lending credence to the above arguments. Thus, it would appear that PIM represents a maximum level of molecular symmetry for biological activity to be manifested efficiently.
Keywords : Host guest, Ogston, prochiral, 2D chirality, van der Waals