Journal
CARBOHYDRATE RESEARCH
Volume 371, Issue -, Pages 68-76Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2013.01.008
Keywords
N-Acetyl-D-glucosamine (GlcNAc); beta-(1 -> 6)-Glucosamine oligosaccharides; Staphylococcus aureus; Poly-N-acetylglucosamine (PNAG); Biofilm; Polysaccharide intercellular adhesin (PIA)
Funding
- Australian Postgraduate Award
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Poly-N-acetylglucosamine (PNAG) saccharides are an important constituent of bacterial biofilms, such as those produced by Staphylococcus aureus. We have developed a simple two-step iterative method for the synthesis of beta-(1 -> 6)-glucosamine oligosaccharides that are structurally similar to PNAG. We illustrate the method with the formation of a pentasaccharide. The key building block is an orthogonally protected N-trifluoroacetamido thioglycoside donor that was added in succession to a glycosyl acceptor, enabling efficient glycosylation of the growing chain. In the second step of the iterative cycle, this building block is quantitatively deprotected at the C-6-hydroxyl position, ready for the next saccharide addition. Building from an azido-functionalised GlcNAc monosaccharide acceptor, the pentasaccharide was synthesised in seven steps in an overall yield of 25%. (C) 2013 Elsevier Ltd. All rights reserved.
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