Chemical Synthesis of Glycosyl Boranophosphates Using Phosphonic Acid Derivatives

Abstract

Glycosyl phosphate repeating structures are found in capsular polysaccharides of some of Neisseria meningitidis and Streptococcus pneumoniae and lipophosphoglycans of Leishmania. Although capsular polysaccharides and lipophosphoglycans play immunologically pivotal roles, their synthesis remains challenging. In this research, a glycosyl boranophosphate, where one of the nonbridging oxygen atoms is replaced with a borano group, is focused on as a key compound for the efficient synthesis of glycosyl phosphate derivatives. Moreover, the author developed the stereocontrolled synthesis of glycosyl boranophosphates to leverage them as probes for the functional elucidation of glycosyl phosphates and pharmaceutical candidates.