165883-85-2Relevant academic research and scientific papers
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.
Comprehensive and uniform synthesis of all naturally occurring phosphorylated phosphatidylinositols
Kubiak, Robert J.,Bruzik, Karol S.
, p. 960 - 968 (2007/10/03)
Studies of cellular signal transduction mechanisms involving receptor-mediated generation of inositol phosphates and phosphorylated phosphatidylinositols require easy access to these naturally occurring products. Although numerous synthetic methods have been developed during the past decade, most of these methods suffer from excessive length and lack of generality. In this work we describe the comprehensive and uniform synthesis of all naturally occurring phosphatidylinositols such as phosphatidylinositol, phosphatidylinositol 3-phosphate, 4-phosphate, 5-phosphate, 3,4-bisphosphate, 3,5-bisphosphate, 4,5-bisphosphate, and 3,4,5-trisphosphate, featuring both saturated and unsaturated fatty acid chains.
A versatile approach to PI(3,4)P2, PI(4,5)P2, and PI(3,4,5)P3 from L-(-)-Quebrachitol
Qiao, Lixin,Hu, Youhong,Nan, Fajun,Powis, Garth,Kozikowski, Alan P.
, p. 115 - 117 (2007/10/03)
(matrix presented) PI(3,4)P2 R1 = R2 = PO3H2, R3 = H ; L-(-)-quebrachitol PI(4,5)P2 R1 = H, R2 = R3 = PO3H2 ; PI(3,4,5)Psu
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 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 1-O-(1,2-DI-O-PALMITOYL-SN-GLYCERO-3-PHOSPHO)-D-MYO-INOSITOL 4,5-BISPHOSPHATE: AN ANALOGUE OF NATURALLY OCCURING (Ptd)Ins(4,5)P2
Dreef, C. E.,Elie, C. J. J.,Hoogerhout, P.,Marel, G. A. van der,Boom, J. H. van
, p. 6513 - 6516 (2007/10/02)
Optically active 2,3,6-tri-O-benzyl-4,5-di-O-(trans-prop-1-enyl)-D-myo-inositol and 1,2-di-O-palmitoyl-sn-glycerol were coupled using mono- and bifunctional phosphitylating reagents to yield, after final removal of all benzyl-protecting groups the chiral title compound.
