Synthesis of disaccharides containing 6-deoxy-α-L-talose as potential heparan sulfate mimetics.
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 a-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 a-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.
Drug Design Group, Progen Pharmaceuticals Ltd, Brisbane QLD 4076, Australia. v.ferro@uq.edu.au
Jon K
JK
Fairweather
Ligong
L
Liu
Tomislav
T
Karoli
Vito
V
Ferro
D032701:Biomimetics; D003837:Deoxy Sugars / Q000737:chemistry*; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D006497:Heparan Sulfate / Q000737:chemistry*; D006601:Hexoses / Q000737:chemistry*
D003837:Deoxy Sugars; D004187:Disaccharides; D006497:Heparan Sulfate; D006601:Hexoses; C011754:6-deoxytalose