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Synlett 2000; 2000(6): 0820-0822
DOI: 10.1055/s-2000-6690
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A Sialyl-Lewis A-Asparagine Building Block for Glycopeptide-Synthesis

Karen Peilstöcker* , Horst Kunz
  • *Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10 - 14, D-55099 Mainz, Germany; Fax +49 6131 39-22334; E-mail: hokunz@mail.uni-mainz.de
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Publication Date:
31 December 2000 (online)

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Using the azido group as the anomeric protection a Sialyl Lewis A tetrasaccharide was synthesized from N-acetylglucosamine via the type 1 lactosamine and Lewis A intermediates. After reduction of the azido group, coupling with Fmoc α-allyl aspartate and Pd(0)-catalyzed deallylation, the Sialyl Lewis A asparagine building block was obtained.

Sialyl Lewis A antigen - oligosaccharide synthesis - regioselective sialylation - glycosyl azides - glycopeptides