Timmons Shannon C, Jakeman David L
Department of Chemistry, Dalhousie University, Halifax, NS, Canada.
Org Lett. 2007 Mar 29;9(7):1227-30. doi: 10.1021/ol063068d. Epub 2007 Mar 6.
[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.
[结构：见正文]。使用勒洛伊尔糖基转移酶制备具有生物学相关性的寡糖和糖缀合物需要获得糖核苷二磷酸，而众所周知，这些物质难以高效合成和纯化。我们报道了一种新颖的立体选择性方法，通过用核苷5'-二磷酸直接取代酰化糖基溴化物来制备UDP-α-D-甘露糖、GDP-α-D-甘露糖、UDP-β-L-岩藻糖和GDP-β-L-岩藻糖。
