Selenoglycosides in Carbohydrate Synthesis

Abstract

Oligosaccharides and glycoconjugates are important for understanding biological functions. A major obstacle in glycobiology and glycomedicine is the limited availability of structurally-defined, homogeneous oligosaccharides and glycoconjugates. Advancements in these areas depend on the ability to access synthetic complex carbohydrates. As such, efforts to advance our understanding of glycosylation as well as methods to form glycosidic bonds in stereocontrolled and regiocontrolled ways are consistently being made. To this end, there is a class of glycosyl donors that is underdeveloped in comparison to other chalcogen-derived donors: selenoglycosides. Similar to the use of organoselenium compounds as synthetic handles in organic synthesis, selenoglycosides are useful tools in carbohydrate synthesis. The use of selenoglycosides as glycosyl donors, however, has been limited to phenyl selenoglycosides due to the lack of robust synthetic methods to prepare them. Our group has developed methodology to access a variety of aryl selenoglycosides not previously reported. Our goal is to apply these novel compounds to expand the applicability of selenoglycosides in carbohydrate synthesis.