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

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DOIResolve DOI: http://doi.org/10.1021/jo026569v
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TypeArticle
Journal titleJournal of Organic Chemistry
ISSN0022-3263
1520-6904
Volume68
Issue6
Pages24262431; # of pages: 6
Subjectoligosaccharide
AbstractA 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
LanguageEnglish
AffiliationNRC Institute for Biological Sciences; National Research Council Canada
Peer reviewedYes
NRC numberYAN2003
NPARC number9370891
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Record identifier365b22d4-8f5c-4b21-a0a2-df9835fe5840
Record created2009-07-10
Record modified2017-04-11
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