221356-64-5Relevant academic research and scientific papers
Synthesis of adenophostin A and congeners modified at glucose
Marwood, Rachel D.,Riley, Andrew M.,Jenkins, David J.,Potter, Barry V. L.
, p. 1935 - 1947 (2007/10/03)
A convergent route is described to the super-potent lo-wyo-inositol 1,4,5-trisphosphate receptor agonist adenophostin A (2) and analogues 5 and 7, in which the glucose bisphosphate unit is replaced by corresponding xylose bisphosphate and mannose bisphosphate units respectively. Adenosine was converted into its 2′,3′-O-p-methoxybenzylidene derivative 8ab, which was selectively N6-dimethoxytritylated by a transient protection method. 5′-O-Benzylation followed by reductive acetal cleavage gave, after separation from its 3′-O-p-methoxybenzyl isomer, the versatile glycosyl acceptor 5′-O-benzyl-N 6-dimethoxytrityl-2′-O-p-methoxybenzyladenosine 13. Coupling of 13 with selectively protected glucopyranosyl, xylopyranosyl or mannopyranosyl dimethyl phosphites gave the required 3′-O-α-pyranosyl adenosine derivatives. Acidic hydrolysis gave corresponding N6-unprotected triols which were phosphitylated using bis(benzyloxy)(diisopropylamino)phosphine and imidazolium Inflate without further N6-protection. Deprotection gave the target trisphosphates 2,5 and 7. Synthetic adenophostin A (2) was identical with a sample of natural material in all respects. Analogues 5 and 7 will be useful for structure-activity studies on the adenophostins. The Royal Society of Chemistry 2000.
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.
