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Glycobiology Advance Access published online on December 8, 2004
Glycobiology, doi:10.1093/glycob/cwi020
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© Oxford University Press 2004; all rights reserved.
Received September 21, 2004
Revised November 30, 2004
Accepted December 2, 2004

Article

Glucan-like synthetic oligosaccharides - Iterative synthesis of linear oligo-{beta}-(1,3)-glucans and immunostimulatory effects

Frank Jamois 1, Vincent Ferrières 2, Jean-Paul Guégan 2, Jean-Claude Yvin 1, Daniel Plusquellec 2, and Vaclav Vetvicka 3*

1 Laboratoire Goëmar, ZAC La Madeleine, Avenue du Général Patton, 35400 Saint Malo, France
2 Synthèses et Activations de Biomolécules, UMR CNRS 6052, Ecole Nationale Supérieure de Chimie de Rennes, Avenue du Général Leclerc, F-35700 Rennes, France
3 University of Louisville, Department of Pathology, Louisville, KY, USA

* To whom correspondence should be addressed.
Vaclav Vetvicka, E-mail: Vetvickavaclav{at}netscape.net


  Abstract

Small reducing and linear oligo-{beta}-(1,3)-glucans, which are able to act as phytoallexin elicitors or as immunostimulating agents in anti-cancer therapy, were synthesized according to an iterative strategy which involved a unique key monosaccharidic donor 8. In order to avoid anomeric mixtures, the reducing entity of the target oligomers was first locked with benzyl alcohol and further selective deprotection of the 3-OH with DDQ afforded building block 9 as an acceptor. The latter was then used in a second cycle of glycosylation/deprotection to afford disaccharide 11 and successive reiterations of this process provided the desired oligomers. Unusual conformational behaviors were observed by standard NMR sequences and supported by NOESY studies. Finally, removal of protecting groups afforded free tri-, tetra- and pentaglucosides in good overall yields. Two oligosaccharides representing linear laminaritetraose and laminaripentaose were compared to the recently described {beta}-(1,3)-glucan Phycarine. Following an intraperitoneal injection, the influx of monocytes and granulocytes into the blood and macrophages into the peritoneal cavity was comparable to that caused by Phycarine. Similarly, both oligosaccharides stimulated phagocytic activity of granulocytes and macrophages. Using ELISA assay, we also demonstrated a significant stimulation of secretion of IL-1{beta}. Taken together, these results suggest that the synthetic oligosaccharides have similar stimulatory effects as natural {beta}-(1,3)- glucans.

Keywords: Carbohydrates; Glycosylation; Glycosides; Oligosaccharides; Immunostimulation.
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