181777-23-1Relevant academic research and scientific papers
C-Glycoside based mimics of D-myo-inositol 1,4,5-trisphosphate
Rosenberg, Heidi J.,Riley, Andrew M.,Correa, Vanessa,Taylor, Colin W.,Potter, Barry V.L.
, p. 7 - 16 (2007/10/03)
Epimeric C-glycoside based polyphosphates, α- and β-D-glucopyranosylmethanol 3,4,1'-trisphosphates (8 and 9) were prepared from D-glucose. The key intermediate, allyl 2,6-di-O-benzyl-α-D-glucopyranoside, was prepared in five steps (67% yield) from allyl α-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)P3 receptor ligands. (C) 2000 Elsevier Science Ltd.
Simplification of adenophostin a defines a minimal structure for potent glucopyranoside-based mimics of D-myo-inositol 1,4,5-trisphosphate
Marwood, Rachel D.,Riley, Andrew M.,Correa, Vanessa,Taylor, Colin W.,Potter, Barry V. L.
, p. 453 - 458 (2007/10/03)
The synthesis of 1-O-[(3S,4R)-3-hydroxytetrahydrofuran-4-yl]-α-D- glucopyranoside 3,4,3'trisphosphate (7), a novel Ca2+ mobilising agonist at the Ins(1,4,5)P3 receptor, designed by excision of two motifs of adenophostin A is reported, defining a potential minimal structure for potent glucopyranoside-based agonists of Ins(1,4,5)P3 receptors.
A Ca2+-mobilising carbohydrate-based polyphosphate: Synthesis of 2- hydroxyethyl α-D-glucopyranoside 2',3,4-trisphosphate
Jenkins, David J.,Potter, Barry V.L.
, p. 169 - 182 (2007/10/03)
Two routes to a glucose-based mimic of the second messenger 1D-myo- inositol 1,4,5-trisphosphate related to adenophostin A are described. Fischer glycosidation of D-glucose with allyl alcohol in the presence of a strong cation-exchange resin gave a 7:3 α:β-anomeric mixture of allyl glucopyranosides (5ab) from which the pure α anomer 5a was isolated by crystallisation. Treatment of 5ab with 1.05 equiv of dibutyltin oxide followed by 2.1 equiv of benzoyl chloride gave allyl 2,6-di-O-benzoyl-α-D- glucopyranoside, which was converted in 3 steps into allyl 2,6-di-O-benzyl- 3,4-O-isopropylidene-α-D-glucopyranoside (4). Alternatively, treatment of 5a with 2.5 equiv of dibutyltin oxide followed by benzyl bromide gave allyl 2,6-di-O-benzyl-α-D-glucopyranoside (9) which was also converted into 4. Compound 4 was elaborated to the phosphorylation precursor 2-hydroxyethyl 2,6-di-O-benzyl-α-D-glucopyranoside (12) in a convenient one-pot reaction, and 12 was phosphorylated and deblocked to afford 2-hydroxyethyl α-D- glucopyranoside 2',3.4-trisphosphate. The 2,6-di-O-benzyl derivative 9 was converted in high yield into 2,6-di-O-benzyl-3,4-di-O-(p-methoxybenzyl)-D- glucopyranose, a useful intermediate for the synthesis of adenophostin A and related compounds.
