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Beilstein J Org Chem. 2012;8:1601-9. doi: 10.3762/bjoc.8.183. Epub 2012 Sep 21.

Automated synthesis of sialylated oligosaccharides.

Author information

1
Max-Planck-Institute of Colloids and Interfaces, Department of Biomolecular Systems, Am Mühlenberg 1, 14476 Potsdam, Germany ; Freie Universität Berlin, Institute of Chemistry and Biochemistry, Arnimallee 22, 14195 Berlin, Germany.

Abstract

Sialic acid-containing glycans play a major role in cell-surface interactions with external partners such as cells and viruses. Straightforward access to sialosides is required in order to study their biological functions on a molecular level. Here, automated oligosaccharide synthesis was used to facilitate the preparation of this class of biomolecules. Our strategy relies on novel sialyl α-(2→3) and α-(2→6) galactosyl imidates, which, used in combination with the automated platform, provided rapid access to a small library of conjugation-ready sialosides of biological relevance.

KEYWORDS:

automated synthesis; disaccharide building blocks; sialic acid; sialosides; solid-phase synthesis

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