Studies towards a scalable synthesis of N-acetyl-L-fucosamine

Abstract

The following describes two attempted syntheses of the rare sugar N-acetyl-L-fucosamine (L-FucNAc) from the inexpensive and readily available L-rhamnose. The syntheses will each involve a protection, oxidation, and reduction strategy in the inversion of the stereochemistry about two sterocenters in L-rhamnose, as well as the introduction of nitrogen at the C-2 position. N-Acetyl-L-fucosamine is one of three carboydrate components of the capsular polysaccharide (CP) of Staphylococcus aureus, which protects the bacterium from the body's immune response. The termination of the CP may provide alternative therapies against S. aureus and possibly other pathogens.