Organic Reactions and Syntheses in Water Solution

Columbia University, New York NY

Investigators

Abstract

With this renewal award the Organic and Macromolecular Chemistry Program supports the work of Dr. Ronald Breslow in the Department of Chemistry at Columbia University in New York City. The work proposed includes both the extension of previous work and exploration of new areas, including: 1) extending regioselective steroid hydroxylation to include terpenes such as beta-carotene, 2) exploring bis-cyclodextrin metal catalysts for ester hydrolysis, 3) preparing catalysts which can bind to substrates both at the metal and at attached cyclodextrin rings, and 4) using computer calculations to investigate transition state geometries and their dependence on hydrophobic effects. The aim of the work to be carried out by Dr. Breslow is to understand and develop organic reactions in water solution, for example the selective hydroxylation of steroids using synthetic mimics of cytochrome P-450 enzymes. The molecular recognition which is required for regiospecificity and stereospecificity is based on hydrophobic (water avoiding) interactions of the substrate with the catalyst in the aqueous environment. The work could lead to useful pharmaceutical applications, and is expected to provide excellent training for those working under Dr. Breslow's direction.