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C-glycoside based mimics of D-myo-inositol 1,4,5-trisphosphate
H J Rosenberg1, A M Riley, V Correa
1Department of Pharmacy and Pharmacology, University of Bath, UK.
Carbohydrate Research
|November 22, 2000
Abstract:
Epimeric C-glycoside based polyphosphates, alpha- and beta-D-glucopyranosylmethanol 3,4,1'-trisphosphates (8 and 9) were prepared from D-glucose. The key intermediate, allyl 2,6-di-O-benzyl-alpha-D-glucopyranoside, was prepared in five steps (67% yield) from allyl alpha-D-glucopyranoside without the need for chromatography. Compounds 8 and 9 were shown to be full agonists at the Ins(1,4,5)P3 receptors of permeabilised hepatocytes, but with markedly different potencies. Such C-glycoside analogues are worthy of further development as Ins(1,4,5)P, receptor ligands.