| Alternative title | Simplifying oligosaccharide synthesis: efficient synthesis of lactosamine and siaylated lactosamine oligosaccharide donors |
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| Download | - View final version: Simplifying oligosaccharide synthesis: efficient synthesis of lactosamine and sialylated lactosamine oligosaccharide donors (PDF, 341 KiB)
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| DOI | Resolve DOI: https://doi.org/10.1021/jo026569v |
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| Author | Search for: Yan, Fengyand1; Search for: Mehta, Seema1; Search for: Eichler, Eva1; Search for: Wakarchuk, Warren W.1; Search for: Gilbert, Michel1; Search for: Schur, Melissa J.1; Search for: Whitfield, Dennis M.1 |
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| Affiliation | - National Research Council of Canada. NRC Institute for Biological Sciences
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| Format | Text, Article |
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| Subject | oligosaccharide |
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| Abstract | A practical sequence is described for converting d-glucosamine into peracetylated Gal(β-1,4)GlcNTroc(β1-S)Ph and Neu5Ac(α-2,3)Gal(β-1,4)GlcNTroc(β1-S)Ph building blocks using a synthetic strategy based on chemoenzymatic oligosaccharide synthesis. The known trichloroethoxycarbonyl, N-Troc, protecting group was selected as a suitable protecting group for both enzymatic and chemical reaction conditions. These oligosaccharide building blocks proved effective donors for the β-selective glycosylation of the unreactive OH-3 of a polymeric PEG-bound acceptor and for the axial OH-2 of a mannose acceptor in good yields. The resulting complex oligosaccharides are useful for vaccine and pharmaceutical applications. |
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| Publication date | 2003-02-21 |
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| Publisher | American Chemical Society |
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| In | |
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| Language | English |
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| Peer reviewed | Yes |
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| NRC number | YAN2003 |
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| NPARC number | 23002007 |
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| Export citation | Export as RIS |
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| Report a correction | Report a correction (opens in a new tab) |
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| Record identifier | 11ce3181-b07f-4063-ab6f-6095c389abb0 |
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| Record created | 2017-07-17 |
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| Record modified | 2020-10-30 |
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