Synthesis of Iminosugar-Containing KRN7000 Analogues

被引：1

作者：

Zhang, Lei ^{[1
]}

Ye, Xin-Shan ^{[1
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Xue Yuan Rd 38, Beijing 100191, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2017年 / 35卷 / 06期

基金：

中国国家自然科学基金;

关键词：

KRN7000; analogue; glycolipid; alpha-GalCer; iminosugar; synthesis; KILLER T-CELLS; C-GALACTOSYL CERAMIDE; ALPHA-GALACTOSYLCERAMIDE; IMMUNOSTIMULATORY ACTIVITIES; GLYCOSIDE ANALOG; NKT CELLS; DERIVATIVES; GLYCOLIPIDS; AGENTS; RECOGNITION;

D O I：

10.1002/cjoc.201600862

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Three new iminosugar-containing KRN7000 (also referred to as alpha-GalCer) analogues were designed and synthesized. In the design, the galactose moiety of KRN7000 was replaced by iminosugars and the iminosugar structures were connected with ceramide in different manners with a C-glycosidic bond instead of the O-glycosidic bond. To our knowledge, this is the first report in which iminosugars are incorporated in KRN7000 structure modifications. The synthetic compounds were evaluated for their ability to stimulate cytokine release. The results may benefit better understanding of structure-activity relationships and facilitate future design of more KRN7000 derivatives.

引用

页码：1001 / 1008

页数：8

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