180979-80-0Relevant 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.
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 (2007/10/03)
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 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.