Synthesis of a Glycosylphosphatidylinositol Anchor Derived from Leishmania donovani That Can Be Functionalized by Cu-Catalyzed Azide-Alkyne Cycloadditions

被引：18

作者：

Ding, Ning ^{[1
,2
]}

Li, Xiuru ^{[2
]}

Chinoy, Zoeisha S. ^{[2
,3
]}

Boons, Geert-Jan ^{[2
,3
,4
,5
]}

机构：

[1] Fudan Univ, Sch Pharm, Dept Med Chem, 826 Zhangheng Rd, Shanghai 201203, Peoples R China

[2] Univ Georgia, Complex Carbohydrate Res Ctr, 315 Riverbend Rd, Athens, GA 30602 USA

[3] Univ Georgia, Dept Chem, 315 Riverbend Rd, Athens, GA 30602 USA

[4] Univ Utrecht, Dept Chem Biol & Drug Discovery, Utrecht Inst Pharmaceut Sci, Univ Sweg 99, NL-3584 CG Utrecht, Netherlands

[5] Univ Utrecht, Bijvoet Ctr Biomol Res, Univ Sweg 99, NL-3584 CG Utrecht, Netherlands

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 14期

基金：

美国国家卫生研究院;

关键词：

CHEMICAL-SYNTHESIS; CLEAVAGE; ACID; LIPOPHOSPHOGLYCAN; PROMASTIGOTES; BIOLOGY; GPIS;

D O I：

10.1021/acs.orglett.7b01703

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A flexible assembly Strategy has been developed for the synthesis of Leishmania donovani GPI anchors that bear a clickable alkyne tag. This strategy is based on the use of the 2-naphthylnaethyl (Nap) ethers and levulinoyl (Lev) ester for permanent:protection of hydroxyls.; Removal of seven. Nap ethers by 2,3-clichloro-5,6-dicyano-J,4-benzoquifione made it posible to prepare GPIs having an alkyne funationality that could be modified by Cu(I)-catalyzed [3 + 2] cycloadditions to install tags for imaging studies.

引用

页码：3827 / 3830

页数：4

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