160247-11-0Relevant articles and documents
Synthesis of dipalmitoyl phosphatidylinositol 3,4-bis(phosphate) and 3,4,5-tris(phosphate) and their enantiomers
Grove, Simon J. A.,Holmes, Andrew B.,Painter, Gavin F.,Hawkins, Phillip T.,Stephens, Leonard R.
, p. 1635 - 1636 (1997)
The dipalmitoyl derivatives 4 and 5 of 3-phosphorylated myo-inositol phospholipids 2 and 3 and their enantiomers are synthesised from homochiral myo-inositol precursors 6 and 11; they serve as biological probes for cell signal transduction.
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.
Rapid and efficient routes to phosphatidylinositol 3,4,5-trisphosphates via myo-inositol orthobenzoate
Sureshan, Kana M.,Riley, Andrew M.,Potter, Barry V.L.
, p. 1923 - 1926 (2007/10/03)
Efficient routes to two phosphatidylinositol 3,4,5-trisphosphate [PtdIns(3,4,5)P3] analogues with different acyl chains have been developed by using cheaply available myo-inositol as the starting material. The high yield of the orthobenzoate derivative, preferential formation of the required protected inositol diastereomer in its desymmetrization and ease of separation make the synthesis expedient, economical and high yielding. Due to the inherent problem of racemization of diacylglycerol (DAG), the synthesis of phosphatidylinositol phosphates [PIPns] with unambiguous stereochemical purity has always been difficult. Our methodology excludes the possibility of racemization in the DAG unit and thus provides access to PtdIns(3,4,5)P3 of high optical purity. Since the acyl functionalities are introduced last, the methodology reported is amenable to the synthesis of PtdIns(3,4,5)P3 with any acyl chain (or even a library of analogues).
Chiral desymmetrisation of myo-inositol 1,3,5-orthobenzoate gives rapid access to precursors for second messenger analogues
Riley, Andrew M.,Godage, H. Yasmin,Mahon, Mary F.,Potter, Barry V. L.
, p. 171 - 174 (2007/10/03)
Chiral desymmetrisation of myo-inositol 1,3,5-orthobenzoate via the formation of diastereoisomeric bis[(1S)-(-)-camphanate] esters provides a convenient and fast route to precursors for biologically important inositol phosphates and lipids, and to synthet
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.
A unified approach to unambiguous synthesis of the phosphatidylinositol-3-phosphates. Involved in intracellular signal transduction
Aneja, Sarla G.,Parra, Alejandro,Stoenescu, Caterina,Xia, Wenyu,Aneja, Rajindra
, p. 803 - 806 (2007/10/03)
A unified approach to unambiguous synthesis of the phosphatidylinositol-3-phosphates involved in intracellular signalling is illustrated by the synthesis of 1D-1-(1',2'- '-dihexadecanoyl-sn-glycero-3'-phospho)-myo-inositol-3,4,5-trisphosphate.
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 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
