Liu Chunjuan, Skogman Fredrik, Cai Ye, Lowary Todd L
Department of Chemistry and Alberta Ingenuity Centre for Carbohydrate Science, Gunning-Lemieux Chemistry Centre, University of Alberta, Edmonton, Canada AB T6G 2G2.
Carbohydr Res. 2007 Dec 28;342(18):2818-25. doi: 10.1016/j.carres.2007.08.020. Epub 2007 Sep 5.
Described is the synthesis of the trisaccharide alpha-D-Manp-(1-->3)-alpha-D-Manp-(1-->3)-beta-D-GlcpNAcO(CH2)8N3, the glycan portion of which corresponds to the 'adaptor-primer' moiety linking the O-chain and core oligosaccharide in the lipopolysaccharide of several Escherichia coli and Klebsiella pneumoniae serotypes. This report represents the first synthesis of this trisaccharide motif, and in the route involved, a key step is a [2+1] coupling of a protected Manp-(1-->3)-alpha-D-Manp glycosyl donor with a GlcpNAc acceptor. The azido group was included in the target to facilitate future preparation of neoglycoconjugates.
本文描述了三糖α-D-甘露糖基-(1→3)-α-D-甘露糖基-(1→3)-β-D-葡萄糖胺基乙酰氧基(CH2)8N3的合成，其聚糖部分对应于几种大肠杆菌和肺炎克雷伯菌血清型脂多糖中连接O链和核心寡糖的“衔接子-引物”部分。本报告代表了该三糖基序的首次合成，在所涉及的路线中，关键步骤是受保护的甘露糖基-(1→3)-α-D-甘露糖基糖基供体与葡萄糖胺基乙酰受体的[2+1]偶联。目标产物中包含叠氮基以方便未来新糖缀合物的制备。
