149091-92-9Relevant academic research and scientific papers
IP3 Receptor-Ligand. 1: Synthesis of Adenophostin A
Hotoda, Hitoshi,Takahashi, Masaaki,Tanzawa, Kazuhiko,Takahashi, Shuji,Kaneko, Masakatsu
, p. 5037 - 5040 (1995)
Adenophostin A, a potent IP3 receptor-agonist, was synthesized.The basic skeleton with 3'-O-(α-D-glucosyl)adenosine was constructed by AgClO4-γ-collidine-promoted glycosylation employing 2-O-benzyl-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide
Adenophostins A and B: Potent agonists of inositol-1,4,5-trisphosphate receptor produced by Penicillium brevicompactum: Structure elucidation
Takahashi,Kinoshita,Takahashi
, p. 95 - 100 (1994)
Adenophostins A (1, C16H26N5O18P3) and B (2, C18H28N5O19P3), potent agonists of inositol-1,4,5-trisphosphate (InsP3) receptor, were isolated from the culture broths of Penicillium brevicompactum SANK 11991 and SANK 12177. Hydrolysis of 2 with aq NaOH gave 1. Oxidation of 2 with NaNO2 gave the hypoxanthine derivative (3). Treatment of 1 or 2 with alkaline phosphatase gave 4 and 5. Treatment of 4 with α-glucosidase gave adenosine. Thus, their structures were deduced to be adenosine nucleotides by NMR, MS and the enzymatic degradation. The inhibitory constants (Ki value) of 1, 2, 3 and InsP3 itself for binding to the InsP3 receptor were 0.18 nM, 0.18 nM, 0.29 nM and 15nM, respectively.
Adenophostin A and analogues modified at the adenine moiety: Synthesis, conformational analysis and biological activity
Borissow, Charles N.,Black, Steven J.,Paul, Michael,Tovey, Stephen C.,Dedos, Skarlatos G.,Taylor, Colin W.,Potter, Barry V. L.
, p. 245 - 252 (2005)
The synthesis of adenophostin A (2) and two analogues [etheno adenophostin (4) and 8-bromo adenophostin (5)] modified at the adenine moiety, is reported. A combination of NMR analysis and molecular modelling was used to compare their structures in solutio
Synthesis of adenophostin A
Marwood, Rachel D.,Correa, Vanessa,Taylor, Colin W.,L. Potter, Barry V.
, p. 397 - 403 (2007/10/03)
The natural product and potent agonist of the D-myo-inositol 1,4,5-trisphosphate receptor, adenophostin A, was synthesised from adenosine and D-glucose using efficient methodology. The synthetic material was equipotent with naturally occurring adenophosti
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.
An expeditious route to the synthesis of adenophostin A
Van Straten, Nicole C. R.,Van der Marel, Gijsbert A.,Van Boom, Jacques H.
, p. 6509 - 6522 (2007/10/03)
Glycosylation of 1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranose (8) with ethyl 3,4,6-tri-O-acetyl-2-O-1-thio-α/β-D-glucopyranoside (7) under the agency of N-iodosuccinimide and trifluoromethanesulfonic acid afforded α-linked dimer 10 in 95% yield. Acetylation of 13, obtained after hydrogenation of 10 followed by pivaloylation of 11 (→12) and deacetonation, yielded penta-acetate 14. Vorbruggen-type condensation of 14 with bis-trimethylsilyl 6-N-benzoyladenine (9) gave adenosyl glucoside 17. Deacetylation of 17 resulted in migration of the pivaloyl group from the 2'-OH to the 3'-OH of the glucosyl moiety (→18), giving access, after phosphorylation and deprotection, to adenophostin A analog 4 containing two (2'-4')-cis oriented phosphate groups. Vorbrugen-type condensation of 9 with 16, obtained by deacetonation of 10 and subsequent acetylation, gave adenosyl glucoside 22. Protective group manipulations followed by phosphorylation furnished, after deprotection, homogeneous adenophostin A (2) in a high overall yield.
An expeditious route to the synthesis of adenophostin A
Van Straten, Nicole C.R.,Van Der Marel, Gijsbert A.,Van Boom, Jacques H.
, p. 3599 - 3602 (2007/10/03)
Glycosylation of 1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranose (8) with ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-α/β-D-glucopyranoside (7) under the agency of N-iodosuccinimide and trifluoromethanesulfonic acid (cat.) afforded α-linked dimer 10 in 95% yield. Vorbruggen-type condensation of 12, obtained by deacetonation of 10 and subsequent acetylation, with bis-trimethylsilyl N6-benzoyl adenine gave adenosyl glucoside 13. Protective group manipulations followed by phosphorylation furnished, after deprotection, homogeneous 2 in high overall yield.
