Synthesis and biological evaluation of phosphatidylinositol phosphate affinity probes

Stuart J. Conway; James Gardiner; Simon J. A. Grove; Melloney K. Johns; Ze-Yi Lim; Gavin F. Painter; Diane E. J. E. Robinson; Christine Schieber; Jan W. Thuring; Leon S.-M. Wong; Meng-Xin Yin; Antony W. Burgess; Bruno Catimel; Phillip T. Hawkins; Nicholas T. Ktistakis; Leonard R. Stephens; Andrew B. Holmes

doi:10.1039/B913399B

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Organic & Biomolecular Chemistry

Issue 1, 2010

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Synthesis and biological evaluation of phosphatidylinositol phosphate affinity probes

Stuart J. Conway , James Gardiner , Simon J. A. Grove , Melloney K. Johns , Ze-Yi Lim , Gavin F. Painter , Diane E. J. E. Robinson , Christine Schieber , Jan W. Thuring , Leon S.-M. Wong , Meng-Xin Yin , Antony W. Burgess , Bruno Catimel , Phillip T. Hawkins , Nicholas T. Ktistakis , Leonard R. Stephens and Andrew B. Holmes

Org. Biomol. Chem., 2010, 8, 66-76

DOI: 10.1039/B913399B
Received 06 Jul 2009, Accepted 29 Sep 2009
First published on the web 09 Nov 2009

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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 1via 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.

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