221356-68-9Relevant academic research and scientific papers
Synthesis of glucopyranoside-based ligands for D-myo-inositol 1,4,5-trisphosphate receptors
Riley, Andrew M,Jenkins, David J,Marwood, Rachel D,Potter, Barry V.L
, p. 1067 - 1082 (2007/10/03)
Adenophostins A and B are naturally occurring glyconucleotides that interact potently with receptors for D-myo-inositol 1,4,5-trisphosphate, an important second messenger molecule in most cell types. Here we describe the design and synthesis of glucopyranoside-based analogues of adenophostin A lacking the adenine component. The key synthetic strategy involves glycosylation of selectively protected alcohols, derived from methyl β-D-ribofuranoside or 1,4-anhydroerythritol, using glycosyl donors synthesised from 2,6-di-O-benzyl-D-glucopyranose derivatives. Further elaboration and deprotection of the coupled products gave two trisphosphate analogues; methyl 3-O-α-D-glucopyranosyl-β-D-ribofuranoside 2,3′,4′-trisphosphate ("ribophostin") and (3′S,4′R)-3′-hydroxytetrahydrofuran-4′-yl α-D-glucopyranoside 3,4,3′-trisphosphosphate ("furanophostin"). The route to furanophostin was further modified to give (3′S,4′R)-3′-hydroxytetrahydrofuran-4′-yl α-D-glucopyranoside 3′-phosphate 3,4-bisphosphorothioate, the first phosphorothioate-containing adenophostin analogue.
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.
