CARB 92 |
| All naturally occurring N-linked glycoproteins contain the well known Man3GlcNAc2 core oligosaccharide structure. The presence of the β-mannoside linkage at the core of this molecule presents the greatest challenge in its synthesis. Recent studies have indicated that the torsional effect of a 4,6-O-benzylidene ring is critical in achieving β stereospecificity. Consequently, it was hypothesized that any sterically constraining group at the 4' and 6' position should yield a similar effect on the stereospecificity. A structural analog of the Man3 core, with an α-mannose linkage at the 4' position using stoichiometric equivalents of trimethylsilyl triflate was considered an attractive synthetic target. By varying the extent of hydroxyl group protection on the donor sugar, a tetrasaccharide was produced exclusively in 93% yield.
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General Posters
6:00 PM-8:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster
Sci-Mix
Division of Carbohydrate Chemistry |
