2,3-二-O-磺基-α-L-岩藻糖基-(1→3)-2-O-磺基-α-L-岩藻糖基-(1→4)-2,3-二-O-磺基-α-L-岩藻糖基-(1→3)-2-O-磺基-α-L-岩藻糖基-(1→4)-2,3-二-O-磺基-β-L-岩藻糖苷辛酯的合成及生物活性
Synthesis and biological activities of octyl 2,3-di-O-sulfo-alpha-L-fucopyranosyl-(1-->3)-2-O-sulfo-alpha-L-fucopyranosyl-(1-->4)-2,3-di-O-sulfo-alpha-L-fucopyranosyl-(1-->3)-2-O-sulfo-alpha-L-fucopyranosyl-(1-->4)-2,3-di-O-sulfo-beta-L-fucopyranoside.
作者信息
Hua Yuxia, Du Yuguo, Yu Gangli, Chu Shidong
机构信息
Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, PO Box 2871, Beijing 100085, PR China.
出版信息
Carbohydr Res. 2004 Aug 23;339(12):2083-90. doi: 10.1016/j.carres.2004.06.006.
Octyl 2,3-di-O-sulfo-alpha-L-fucopyranosyl-(1-->3)-2-O-sulfo-alpha-L-fucopyranosyl-(1-->4)-2,3-di-O-sulfo-alpha-L-fucopyranosyl-(1-->3)-2-O-sulfo-alpha-L-fucopyranosyl-(1-->4)-2,3-di-O-sulfo-beta-L-fucopyranoside, a fucosyl pentasaccharide with a regular structure resembling the repeating unit of a natural sulfated fucan, was chemically synthesized using a convergent '2+3' strategy. Regioselective 3-O-silylation of beta-thiofucopyranoside and AgOTf-catalyzed glycosylation of the protected glycosyl trichloroacetimidate facilitated a one-pot trisaccharide synthesis. The synthesized target compound showed good antitumor activity in vivo, and promising anticoagulant activity in vitro.
辛基 2,3 - 二 - O - 磺基 - α - L - 岩藻糖基 - (1→3) - 2 - O - 磺基 - α - L - 岩藻糖基 - (1→4) - 2,3 - 二 - O - 磺基 - α - L - 岩藻糖基 - (1→3) - 2 - O - 磺基 - α - L - 岩藻糖基 - (1→4) - 2,3 - 二 - O - 磺基 - β - L - 岩藻糖苷，一种具有类似于天然硫酸化岩藻聚糖重复单元的规则结构的岩藻糖基五糖，采用汇聚式“2 + 3”策略进行化学合成。β - 硫代岩藻糖苷的区域选择性3 - O - 硅烷化和受保护的糖基三氯乙酰亚胺酯的AgOTf催化糖基化促进了一锅法三糖合成。合成的目标化合物在体内显示出良好的抗肿瘤活性，在体外具有有前景的抗凝血活性。
Zotero 插件