LAUSR

The chemical synthesis of ketopentose-5-phosphates that are involved in the pentose phosphate pathway is developed. The ketopentose phosphates, D-ribulose-5-phosphate and D-xylulose-5-phosphate, were prepared in five steps starting from known intermediates. Starting from readily available D-aldopentoses, the reduction of the corresponding furanose derivatives gave key intermediates in the form of aldopentitols. Selective phosphorylation, oxidation, followed by deprotection provided the target molecules. This chemical synthetic method makes such ketopentose phosphates readily available, suggesting that they could be used as assay substrates for mechanistic studies. Since the pentose phosphate pathway is important in cancer cell metabolism, this synthetic methodology provides an opportunity for preparing potential enzymatic inhibitors for use in drug development. To further extend this synthetic methodology, a different protecting group (a trityl group) was employed in the synthesis of two parent ketopentoses (D-ribulose and D-xylulose) in a similar manner.