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Synthesis 2010(18): 3070-3082  
DOI: 10.1055/s-0030-1258157
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Glycocluster Synthesis by Native Chemical Ligation

Johannes W. Wehner, Thisbe K. Lindhorst*
Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn-Platz 3/4, 24098 Kiel, Germany
Fax: +49(431)8807410; e-Mail: tklind@oc.uni-kiel.de;
Further Information

Publication History

Received 21 April 2010
Publication Date:
07 July 2010 (online)

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Abstract

Serine- and mannoside-derived thioesters and a mannosidic cysteine derivative were prepared to test native chemical ligation (NCL) for protecting-group-free synthesis of small glycopeptide clusters, which are valuable tools in the glycosciences. The glycopeptides and glycopeptide clusters, respectively, which were obtained via NCL, bear the potential for dimerization and other derivatization of the thiol functionality.

Key words

carbohydrates - glycopeptides - glycoclusters - native chemical ligation - protecting-group-free synthesis

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