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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.

Type

Journal article

Journal

Carbohydr Res

Publication Date

20/10/2000

Volume

329

Pages

7 - 16

Keywords

Adenosine, Animals, Calcium, Calcium Channels, Calcium Radioisotopes, Calcium Signaling, Dose-Response Relationship, Drug, Glucose, Glycosides, Hepatocytes, Inositol 1,4,5-Trisphosphate, Inositol 1,4,5-Trisphosphate Receptors, Molecular Mimicry, Rats, Receptors, Cytoplasmic and Nuclear