Origins of Stereoselectivity in Peptide-Catalyzed Kinetic Resolution of Alcohols

Abstract

High Resolution Image Download MS PowerPoint Slide The origin of the stereoselectivity of the tetrapeptide-catalyzed kinetic resolution of trans -2- N -acetamidocyclohexanol is investigated by means of density functional theory calculations. Transition states for the functionalization of both ( R, R ) and ( S, S ) substrates were optimized considering all possible conformers. Due to the flexibility of the peptidic catalyst, a large number of transition states had to be located, and analysis of the geometries and energies allowed for the identification of the main factors that control the stereoselectivity.