De novo synthesis of D- and L-fucosamine containing disaccharides

Beilstein J Org Chem. 2013:9:332-41. doi: 10.3762/bjoc.9.38. Epub 2013 Feb 14.

Abstract

The availability of rare monosaccharides that cannot be isolated from natural sources is currently limiting the access to the synthesis and the biological evaluation of complex bacterial cell-surface glycans. Here, we report the synthesis of D- and L-fucosamine building blocks by a de novo approach from L- and D-Garner aldehydes. These differentially protected monosaccharide building blocks were utilized to prepare disaccharides present on the surface of Pseudomonas aeruginosa bacteria.

Keywords: de novo synthesis; fucosamine; glycan; pseudomonas aeruginosa; vaccine.