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

Molecules

Jon K. Fairweather²  Ligong Liu¹  Tomislav Karoli¹ 

[1] id="af1-molecules-17-09790">Drug Design Group, Progen Pharmaceuticals Ltd, Brisbane QLD 4076, Austral

关键词: disaccharides;    heparan sulfate mimetics;    fibroblast growth factors;   

DOI  :  10.3390/molecules17089790

来源: mdpi

【 摘 要 】

A 6-deoxy-α-L-talopyranoside acceptor was readily prepared from methyl α-L-rhamnopyranoside and glycosylated with thiogalactoside donors using NIS/TfOH as the promoter to give good yields of the desired α-linked disaccharide (69–90%). Glycosylation with a 2-azido-2-deoxy-D-glucosyl trichloroacetimidate donor was not completely stereoselective (α:β = 6:1), but the desired α-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.

【 授权许可】

CC BY   
© 2012 by the authors; licensee MDPI, Basel, Switzerland.