Rudolf's Research Blog

Effect of Atropisomerism on the Binding Propensities of α-Hydroxytropolones

Isomers1 are molecules which have the same molecular formula but with different atomic organization. There are two main classes of isomers; structural or constitutional isomers, and spatial or stereoisomers. Stereoisomers have the same bond arrangements, but the geometric orientations of their atoms are different. In a molecule, free rotation about a single bond is basically permitted. Atropisomers2 are a type of stereoisomers in which the rotation of a certain group of atoms about a an asymmetric bond axis is sterically hindered due to intramolecular interactions.

One of the projects currently undergoing in Murelli’s lab is synthesizing a library of a class of organic molecules called α-Hydroxytropolone. Some of these molecules have shown a promising potential as antiviral agents against HBV, HSV-1 and HIV. In synthesizing these molecules, we are also interested in studying the effects of axial chirality, that some of these molecules exhibit. To this end we are collaborating with Prof. Emilio Gallicchio to use computational and molecular modeling methods to investigate how atropisomerism might affect the binding affinity of these newly synthesized molecules to their enzymatic targets.

References

1. Brown, William H.; Foote, Christopher S. Organic Chemistry, 7th Edition, Mary Finch, 2014.

2. Anslyn and Dougherty, Modern Physical Organic Chemistry, University Science Books, 2006.