Synthesis of Disaccharides Containing 6-Deoxy-α-L-talose as Potential Heparan Sulfate Mimetics

被引：7

作者：

Fairweather, Jon K. ^{[1
]}

Liu, Ligong ^{[1
]}

Karoli, Tomislav ^{[1
]}

Ferro, Vito ^{[1
]}

机构：

[1] Progen Pharmaceut Ltd, Drug Design Grp, Brisbane, Qld 4076, Australia

来源：

MOLECULES | 2012年 / 17卷 / 08期

关键词：

disaccharides; heparan sulfate mimetics; fibroblast growth factors; FIBROBLAST-GROWTH-FACTOR; TUMOR-GROWTH; CONFORMATIONAL FLEXIBILITY; GLYCOSIDIC BONDS; OLIGOSACCHARIDES; INHIBITORS; IDENTIFICATION; ANGIOGENESIS; BINDING; FGF-1;

D O I：

10.3390/molecules17089790

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A 6-deoxy-alpha-L-talopyranoside acceptor was readily prepared from methyl alpha-L-rhamnopyranoside and glycosylated with thiogalactoside donors using NIS/TfOH as the promoter to give good yields of the desired alpha-linked disaccharide (69-90%). Glycosylation with a 2-azido-2-deoxy-D-glucosyl trichloroacetimidate donor was not completely stereoselective (alpha:beta = 6:1), but the desired alpha-linked disaccharide could be isolated in good overall yield (60%) following conversion into its corresponding tribenzoate derivative. The disaccharides were designed to mimic the heparan sulfate (HS) disaccharide GlcN(2S,6S)-IdoA(2S). However, the intermediates readily derived from these disaccharides were not stable to the sulfonation/deacylation conditions required for their conversion into the target HS mimetics.

引用

页码：9790 / 9802

页数：13

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