Beilstein J. Org. Chem.2013,9, 332–341, doi:10.3762/bjoc.9.38
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; Introduction
Protein functions are directly
bacterium. In 2001, the P. aeruginosa pilin O-linked glycans were found to be linear trisaccharides that are covalently attached to serine (Figure 1). The O-glycans contain a D-fucosamine residue at the protein-binding site. This unusual monosaccharide is not present in eukaryotes, and therefore may be used
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Graphical Abstract
Figure 1:
Structure of some O-linked glycans found on the cell surface of P. aeruginosa.