Title |
A simple iterative method for the synthesis of β-(1→6)-glucosamine oligosaccharides
|
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Published in |
Carbohydrate Research, February 2013
|
DOI | 10.1016/j.carres.2013.01.008 |
Pubmed ID | |
Authors |
Lucy G. Weaver, Yogendra Singh, Joanne T. Blanchfield, Paul L. Burn |
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%. |
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Geographical breakdown
Country | Count | As % |
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United States | 2 | 8% |
Netherlands | 1 | 4% |
Denmark | 1 | 4% |
Taiwan | 1 | 4% |
Unknown | 20 | 80% |
Demographic breakdown
Readers by professional status | Count | As % |
---|---|---|
Student > Ph. D. Student | 8 | 32% |
Researcher | 5 | 20% |
Professor | 2 | 8% |
Other | 2 | 8% |
Student > Master | 2 | 8% |
Other | 1 | 4% |
Unknown | 5 | 20% |
Readers by discipline | Count | As % |
---|---|---|
Chemistry | 11 | 44% |
Biochemistry, Genetics and Molecular Biology | 5 | 20% |
Medicine and Dentistry | 2 | 8% |
Agricultural and Biological Sciences | 1 | 4% |
Unknown | 6 | 24% |