196306-63-5Relevant academic research and scientific papers
Development of inositol-based antagonists for the d-myo-inositol 1,4,5-trisphosphate receptor
Keddie, Neil S.,Ye, Yulin,Aslam, Tashfeen,Luyten, Tomas,Bello, Davide,Garnham, Clive,Bultynck, Geert,Galione, Antony,Conway, Stuart J.
supporting information; experimental part, p. 242 - 244 (2011/03/20)
The syntheses of four d-myo-inositol 1,4,5-trisphosphate (InsP3) derivatives, incorporating phosphate bioisosteres at the 5-position, are reported. The methyl phosphate ester and sulfate derivatives retain InsP 3 receptor (InsP3
Synthesis and biological evaluation of phosphatidylinositol phosphate affinity probes
Conway, Stuart J.,Gardiner, James,Grove, Simon J. A.,Johns, Melloney K.,Lim, Ze-Yi,Painter, Gavin F.,Robinson, Diane E. J. E.,Schieber, Christine,Thuring, Jan W.,Wong, Leon S.-M.,Yin, Meng-Xin,Burgess, Antony W.,Catimel, Bruno,Hawkins, Phillip T.,Ktistakis, Nicholas T.,Stephens, Leonard R.,Holmes, Andrew B.
scheme or table, p. 66 - 76 (2010/04/29)
The synthesis of the complete family of phosphatidylinositol phosphate analogues (PIPs) from five key core intermediates A-E is described. These core compounds were obtained from myo-inositol orthoformate 1 via regioselective DIBAL-H and trimethylaluminium-mediated cleavages and a resolution-protection process using camphor acetals 10. Coupling of cores A-E with phosphoramidites 34 and 38, derived from the requisite protected lipid side chains, afforded the fully-protected PIPs. Removal of the remaining protecting groups was achieved via hydrogenolysis using palladium black or palladium hydroxide on carbon in the presence of sodium bicarbonate to afford the complete family of dipalmitoyl- and amino-PIP analogues 42, 45, 50, 51, 58, 59, 67, 68, 76, 77, 82, 83, 92, 93, 99 and 100. Investigations using affinity probes incorporating these compounds have identified novel proteins involved in the PI3K intracellular signalling network and have allowed a comprehensive proteomic analysis of phosphoinositide interacting proteins. The Royal Society of Chemistry 2010.
General synthesis of 3-phosphorylated mj'o-inositol phospholipids and derivatives
Painter, Gavin F.,Grove, Simon J. A.,Gilbert, Lan H.,Holmes, Andrew B.,Raithby, Paul R.,Hill, Malcolm L.,Hawking, Phillip T.,Stephens, Leonard R.
, p. 923 - 935 (2007/10/03)
The D-3-phosphorylated wyo-inositol phospholipids PtdIns(3)P, PtdIns(3,4)P2, PtdIns(3,4,5)P3 and PtdIns(3,5)P2 were synthesised from /yo-inositol orthoformate 8. Key transformations included the regioselective DIBAL- and trimethylaluminium-mediated cleavages of wiyo-inositol orthoformate intermediates and a resolution-protection protocol using the camphor acetals 17. The final reductive debenzylation was effected with Pearlman's catalyst [Pd(OH)J in the presence of sodium hydrogen carbonate. The biological properties of the phospholipids were evaluated against various protein kinases (PKB and PDK-1) in which they played an important activation role.
Synthesis of 3-Position-Modified Analogues of myo-Inositol 1,4,5-Trisphosphate, Tools for Investigation of the Polyphosphoinositide Pathway of Cellular Signaling
Liu, Changsheng,Potter, Barry V. L.
, p. 8335 - 8338 (2007/10/03)
Methods for the synthesis of 3-O-(carboxymethyl)- and 3-O-alkylated myo-inositol 1,4,5-trisphosphates in racemic form from myo-inositol have been devised. For DL-3-O-(carboxymethyl)-myo-inositol 1,4,5-trisphosphate, an analogue of myo-inositol 1,3,4,5-tet
Versatile synthesis of myo-inositol phospholipid precursors
Grove, Simon J. A.,Gilbert, Ian H.,Holmes, Andrew B.,Painter, Gavin F.,Hill, Malcolm L.
, p. 1633 - 1634 (2007/10/03)
Homochiral myo-inositol derivatives 16 and 20 and their corresponding enantiomers possessing either the natural or unnatural ring stereochemistry for inositol phospholipids are synthesised from myo-inositol derivatives 8 and 9 respectively using camphor d
SYNTHESIS OF MYO-INOSITOL 1,4,5-TRISPHOSPHATE 3-PHOSPHOROTHIOATE AS AN INHIBITOR OF MYO-INOSITOL 1,3,4,5-TETRAKISPHOSPHATE 3-PHOSPHATASE
Liu, Changsheng,Potter, Barry V. L.
, p. 1605 - 1608 (2007/10/02)
The synthesis of racemic myo-inositol 1,4,5-triphosphate 3-phosphorothioate from myo-inositol is described using a protection/deprotection sequence employing allyl, benzyl and p-methoxybenzyl groups to facilitate selective 3-position thiophosphorylation.
