乳糖硅烷[纠正为拉托硅烷]五糖重复单元的合成。

Synthesis of the pentasaccharide repeating unit of lactosillan [correction of latosillan].

作者信息

Hua Yuxia, Xiao Junjun, Huang Yingshen, Du Yuguo

机构信息

State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China.

出版信息

Carbohydr Res. 2006 Feb 6;341(2):191-7. doi: 10.1016/j.carres.2005.11.007. Epub 2005 Dec 5.

DOI:10.1016/j.carres.2005.11.007

PMID:16332360

Abstract

A pentasaccharide, beta-D-Man-(1-->2)-[beta-D-GlcNAc-(1-->4)]-alpha-L-Rha-(1-->4)-alpha-L-Rha-(1-->4)-alpha-L-Rha-1-OC8H17, representing the repeating unit of latosillan, was convergently synthesized from the building blocks, ethyl 2,3-O-isopropylidene-1-thio-alpha-l-rhamnopyranoside, 2-O-acetyl-3,4,6-tri-O-benzyl-beta-d-glucopyranosyl trichloroacetimidate, and 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-d-glucopyranosyl trichloroacetimidate under standard glycosylation conditions. The target pentasaccharide showed acceptable differentiation-inducing activity on HL-60 cell lines at the dosages of 10-50 microg/mL.

摘要

一种五糖，β-D-甘露糖-（1→2）-[β-D-乙酰氨基葡萄糖-（1→4）]-α-L-鼠李糖-（1→4）-α-L-鼠李糖-（1→4）-α-L-鼠李糖-1-OC8H17，代表拉托西兰的重复单元，在标准糖基化条件下由构建模块2,3-O-异丙叉基-1-硫代-α-L-鼠李吡喃糖苷、2-O-乙酰基-3,4,6-三-O-苄基-β-D-吡喃葡萄糖基三氯乙亚胺酯和3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-β-D-吡喃葡萄糖基三氯乙亚胺酯聚合合成。目标五糖在10-50μg/mL的剂量下对HL-60细胞系显示出可接受的分化诱导活性。