Chemoenzymatic Iterative Synthesis of Difficult Linkages of Oligosaccharides on Soluble Polymeric Supports

A trisaccharide donor containing a cis-Galpα(1→4)Galp linkage was prepared using a synthetic strategy based on chemoenzymatic oligosaccharide synthesis on a soluble polymeric support. Significantly, only retaining glycosyltransferases gave complete reactions, whereas inverting enzymes showed little...

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Veröffentlicht in:	Organic letters 2001-10, Vol.3 (21), p.3265-3268
Hauptverfasser:	Yan, Fengyang, Gilbert, Michel, Wakarchuk, Warren W, Brisson, Jean-Robert, Whitfield, Dennis M
Format:	Artikel
Sprache:	eng
Schlagworte:	Carbohydrate Conformation Glycosylation Glycosyltransferases - chemistry Glycosyltransferases - metabolism Nuclear Magnetic Resonance, Biomolecular Oligosaccharides - chemical synthesis Oligosaccharides - chemistry Polyethylene Glycols Protein Binding Shiga Toxin 1 - metabolism Trisaccharides - chemical synthesis Trisaccharides - metabolism
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Beschreibung
Zusammenfassung:	A trisaccharide donor containing a cis-Galpα(1→4)Galp linkage was prepared using a synthetic strategy based on chemoenzymatic oligosaccharide synthesis on a soluble polymeric support. Significantly, only retaining glycosyltransferases gave complete reactions, whereas inverting enzymes showed little or no activity with poly(ethylene glycol) (MPEG)-bound lactose as an acceptor. The MPEG-attached trisaccharide was shown to bind to Verotoxin-1 by transfer NOE studies through the Galpα(1→4)Galp portion of the molecule.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol016466j