A simple iterative method for the synthesis of beta-(1 -> 6)-glucosamine oligosaccharides

作者：Weaver Lucy G; Singh Yogendra; Blanchfield Joanne T^*; Burn Paul L

来源：Carbohydrate Research, 2013, 371: 68-76.

DOI：10.1016/j.carres.2013.01.008

• N-Acetyl-D-glucosamine (GlcNAc)
• beta-(1 -> 6)-Glucosamine oligosaccharides
• Staphylococcus aureus
• Poly-N-acetylglucosamine (PNAG)
• Biofilm
• Polysaccharide intercellular adhesin (PIA)

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%.

• 出版日期2013-4-19