Stereoselective Phosphorylation of Diols and Carbohydrates with N-Phosphoryl Oxazolidinones: Application to the Rapid Synthesis of Phosphoglycerides

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Many substances in Nature exist as two different forms called enantiomers. These molecules have the same number of atoms and are connected in the same way, except the arrangement of some of the atoms is different. Your hands are both enantiomers - both are made up of the same bits (a palm, one thumb and four different fingers) and all are connected in the same way (thumb, first finger, second finger and so on). However the order of connectivity is different which leads to your left and right hand being related as non-superimposable mirror images. Objects or substances that are non-superimposable mirror images are called chiral. Each of these chiral substances in Nature and many pharmaceutical ingredients have different biological activities and so much effort is devoted to developing chemical reactions that can selectively produce only one of these forms. Research from these laboratories has developed a completely new method for achieving such a transformation by formation of a phosphate ester. Such a reaction is incredibly useful since the products formed from this reaction can be used as chemical building blocks to construct other larger materials. The purpose of this project is to build upon this new methodology and to attempt to make phosphate esters of more complex molecules such as carbohydrates, glycerides and inositols. The phosphate ester products of these reactions are extremely important and valuable materials for use in biology where they can be used as molecular tools to investigate how cells work. The added advantage of our methodology is that it can be carried out selectivity, quickly and in one reaction vessel, significantly simplifying the time and effort required to prepare these substances.We will demonstrate the effectiveness of this work by constructing several biologically active target molecules that will be of use to collaborators in the Department of Genomic Medicine here at the University of Sheffield.We will investigate ways to develop a catalyst for this reaction system that will further simplify the procedure and reduce the cost of production of these highly desirable products even further.