141040-54-2Relevant articles and documents
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.
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
The preparation of racemic and enantiomerically pure myo-inositol derivatives as intermediates for the synthesis of phosphatidylinositol 3-, 3,4-bis-, and 3,4,5-tris-phosphates and for the synthesis of analogues of 1D-myo-inositol 1,3,4,5-tetrakisphosphat
Desai, Trupti,Gigg, Jill,Gigg, Roy,Martin-Zamora, Eloisa
, p. 97 - 133 (2007/10/03)
Details of the products obtained by the tin-mediated allylation and benzylation of 1,2-O-isopropylidene-myo-inositol, which were previously described in a preliminary communication, are provided here. Some of the products from these reactions, particularl
Synthesis of the D-3 series of phosphatidylinositol phosphates
Wang, Da-Sheng,Chen, Ching-Shih
, p. 5905 - 5910 (2007/10/03)
The 3-mono-, 3,4-bis-, and 3,4,5-trisphosphates of L-α-phosphatidyl-D-myo-inositol have been synthesized in their optically active forms from the two enantiomers of 1,2:5,6-di-O-cyclohexylidene-myo-inositol. These chiral precursors were prepared by a facile biocatalytic resolution, in which the 4-butyryl ester of the racemic compound was subjected to enantioselective hydrolysis by porcine pancreatic lipase in a biphasic system. The overall yield from individual chiral precursors ranged from 32% for the 3,4,5-trisphosphate to 39% for the monophosphate.
The preparation, resolution, and phosphorylation of some benzyl ethers of myo-inositol: Intermediates for the synthesis of myo-inositol phosphates of the phosphatidylinositol cycle
Desai,Gigg,Gigg,Payne
, p. 209 - 228 (2007/10/02)
The syntheses of the following chiral compounds are described: 1D-2,3,6-tri-, 1D-2,4,5-tri, 1D-2,5,6-tri-, 1D-1,2,3,4-tetra, 1D-1,2,3,6-tetra-, 1D-1,2,4,5-tetra-, and 1D-2,3,5,6-tetra-0-benzyl-myo-inositol; and 1D-2,5,6-tri-0-benzyl-1-0-p-methoxybenyl- an
Total Synthesis of the Second Messenger Analogue D-myo-Inositol 1- Phosphorothioate 4,5-Biphosphate: Optical Resolution of DL-1-O-Allyl-2,3,6-tri-O-Benzyl-myo-inositol and Fluorescent Labelling of myo-Inositol 1,4,5-Triphposphate
Lampe, Dethard,Mills, Stephen J.,Potter, Barry V. L.
, p. 2899 - 2906 (2007/10/02)
Two routes for the synthesis of the myo-inositol 1,4,5-triphosphate analogue myo-inositol 1-phosphorothioate 4,5-bisphosphate have been devised.DL-2,3,6-Tri-O-benzyl-1-O-(cis-prop-1-enyl)-myo-inositol was prepared from DL-1-O-allyl-2,3,6-tri-O-benzyl-myo-
