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 β-(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%. © 2013 Elsevier Ltd. All rights reserved.
CITATION STYLE
Weaver, L. G., Singh, Y., Blanchfield, J. T., & Burn, P. L. (2013). A simple iterative method for the synthesis of β-(1→6)- glucosamine oligosaccharides. Carbohydrate Research, 371, 68–76. https://doi.org/10.1016/j.carres.2013.01.008
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