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

From National Research Council Canada

Alternative titleSimplifying 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
Subjectoligosaccharide
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.
Publication date
PublisherAmerican Chemical Society
American Chemical Society
LanguageEnglish
Peer reviewedYes
NRC numberYAN2003
NPARC number23002007
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Record identifier11ce3181-b07f-4063-ab6f-6095c389abb0
Record created2017-07-17
Record modified2020-10-30
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