Stereoselective chemical synthesis of sugar nucleotides via direct displacement of acylated glycosyl bromides |
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Authors: | Timmons Shannon C Jakeman David L |
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Institution: | Department of Chemistry, Dalhousie University, Halifax, NS, Canada. |
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Abstract: | structure: see text]. The use of Leloir glycosyltransferases to prepare biologically relevant oligosaccharides and glycoconjugates requires access to sugar nucleoside diphosphates, which are notoriously difficult to efficiently synthesize and purify. We report a novel stereoselective route to UDP- and GDP-alpha-D-mannose as well as UDP- and GDP-beta-L-fucose via direct displacement of acylated glycosyl bromides with nucleoside 5'-diphosphates. |
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