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

From National Research Council Canada

Download
  1. (PDF, 650 KB)
DOIResolve DOI: https://doi.org/10.1021/jo026569v
AuthorSearch for: 1 ; Search for: 1 ; Search for: 1 ; Search for: 1 ; Search for: 1 ; Search for: 1 ; Search for: 1 
Name affiliation
  1. National Research Council Canada. NRC Institute for Biological Sciences
FormatText
TypeArticle
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.
Publication date
PublisherAmerican Chemical Society
LanguageEnglish
Peer reviewedYes
NPARC number23002007
Export citationExport as RIS
Report a correctionReport a correction
Record identifier11ce3181-b07f-4063-ab6f-6095c389abb0
Record created2017-07-17
Record modified2019-03-11
Date modified:
Report a problem on this page