ORGN 279 |
| The stereoselective construction of β-mannosidic bonds is a major challenge in synthetic carbohydrate chemistry, as in most cases conventional glycosidation strategies will favor the formation of α-mannosidic linkages due to both thermodynamic and kinetic reasons. Only recently, efficient synthetic strategies towards these compounds have emerged. In nature, β-linked mannopyranosides are important components of, for example, the N-glycan core structure of glycoproteins and certain cell wall phosphopeptidomannans. The β-(1,2)-mannans of Candida albicans are immunogenic and elicit specific antibodies in humans and animals. In most cases, however, the isolable quantities of natural oligosaccharides are far too low to afford sufficient amounts required for biological evaluation. Accordingly, the scale-up of synthesis and the further development of efficient strategies for such targets is of continuous topical interest. Here, we describe our recent work in the synthesis of fully deprotected β-(1→2)-D-mannopyranosides, some of their glycosides and analogues by application and modification of synthesis strategies developed earlier by Crich and others. The results are discussed in the context and evaluation of some of their potential biological properties.
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Biologically Active Molecules
8:00 AM-12:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Rm. R05, Oral
Division of Organic Chemistry |
