Simplifying oligosaccharide synthesis:  efficient synthesis of lactosamine and siaylated lactosamine oligosaccharide donors

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DOIResolve DOI: https://doi.org/10.1021/jo026569v
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Name affiliation
  1. National Research Council of Canada. NRC Institute for Biological Sciences
FormatText, Article
Journal titleJournal of Organic Chemistry
ISSN0022-3263
1520-6904
Volume68
Issue6
Pages2426–2431
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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PublisherAmerican Chemical Society
LanguageEnglish
Peer reviewedYes
NPARC number23002007
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Record identifier11ce3181-b07f-4063-ab6f-6095c389abb0
Record created2017-07-17
Record modified2020-05-30
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