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Determination of molecular chirality is becoming increasingly important due to the sophistication in mode of action studies of biological reactions and the importance of chiral drugs. The exciton coupled CD, based on through space coupling, is a versatile microscale method with superb sensitivity that can be applied to a variety of problems including biopolymers and clusters in lipids. Applications of the exciton coupled CD method to the following problems exemplify its versatility. 1. Quaternary ammonium salts as chromophores for exciton-coupled CD.1' Exciton coupled circular dichroism is a nonempirical submicrogram scale method for determining absolute configurations and conformations of organic molecules in solution based on the interactions of chromophores which are preexisting in the substrate and/or introduced through derivatizations such as 0- or N-acylation.213 However, the method could not be applied to one major group, i.e., tertiary amines which comprise numerous natural products, particularly alkaloids, and synthetic drugs that exhibit conspicuous biological activities. We have succeeded in extending the CD method to quinuclidines (tertiary amines) through quaternary ammonium salt formation, and have applied this new procedure to the important class of hypocholesterolemic quinuclidines. Of the three conformers conceivable for the salt (l), the conformer shown determines the sign of the split Cotton effect (CE). When the phenylbenzyl group is in the north east sector the transition moments ,of the two chromophores are close to being parallel, hence the chirality is negligible; when it is in the north west sector, the distance between the two chromophores is more remote than that depicted, hence the resulting positive bisignate CD will be of smaller amplitude. OMe

Solving challenging bioorganic problems by exciton coupled CD