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

Weaver, Lucy G., Singh, Yogendra, Blanchfield, Joanne T. and Burn, Paul L. (2013) A simple iterative method for the synthesis of beta-(1 -> 6)-glucosamine oligosaccharides. Carbohydrate Research, 371 68-76. doi:10.1016/j.carres.2013.01.008


Author Weaver, Lucy G.
Singh, Yogendra
Blanchfield, Joanne T.
Burn, Paul L.
Title A simple iterative method for the synthesis of beta-(1 -> 6)-glucosamine oligosaccharides
Formatted title
A simple iterative method for the synthesis of β-(1→6)-glucosamine oligosaccharides
Journal name Carbohydrate Research   Check publisher's open access policy
ISSN 0008-6215
1873-426X
Publication date 2013-04-01
Year available 2013
Sub-type Article (original research)
DOI 10.1016/j.carres.2013.01.008
Open Access Status Not yet assessed
Volume 371
Start page 68
End page 76
Total pages 9
Place of publication Kidlington, Oxford, United Kingdom
Publisher Pergamon
Language eng
Subject 1602 Analytical Chemistry
1303 Biochemistry
1605 Organic Chemistry
Abstract 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%.
Keyword N-Acetyl-D-glucosamine (GlcNAc)
beta-(1 -> 6)-Glucosamine oligosaccharides
β-(1→6)-Glucosamine oligosaccharides
Staphylococcus aureus
Poly-N-acetylglucosamine (PNAG)
Biofilm
Polysaccharide intercellular adhesin (PIA)
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Centre for Organic Photonics and Electronics
Official 2014 Collection
School of Chemistry and Molecular Biosciences
 
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