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Issue 8, 1999
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General synthesis of 3-phosphorylated myo-inositol phospholipids and derivatives

Abstract

The D-3-phosphorylated myo-inositol phospholipids PtdIns(3)P, PtdIns(3,4)P2, PtdIns(3,4,5)P3 and PtdIns(3,5)P2 were synthesised from myo-inositol orthoformate 8. Key transformations included the regioselective DIBAL- and trimethylaluminium-mediated cleavages of myo-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)2] 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.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1999, 923-936
Article type
Paper

General synthesis of 3-phosphorylated myo-inositol phospholipids and derivatives

G. F. Painter, S. J. A. Grove, I. H. Gilbert, A. B. Holmes, P. R. Raithby, M. L. Hill, P. T. Hawkins and L. R. Stephens, J. Chem. Soc., Perkin Trans. 1, 1999, 923
DOI: 10.1039/A900278B

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