期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 8, 期 1, 页码 66-76出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/b913399b
关键词
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资金
- BBSRC
- EPSRC
- Australian Research Council, Discovery Project [DP0770668]
- NHMRC [487922]
- CSIRO
- VESKI (Victorian Endowment for Science, Knowledge and Innovation)
- Daiso Co., Ltd, Japan
- Cambridge Commonwealth Trust
- Universities UK
- New Hall
- Cambridge and Tan Kar Kee Foundation, Singapore
- Biotechnology and Biological Sciences Research Council [BBS/E/B/0000C221, BBS/E/B/00001221] Funding Source: researchfish
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.
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