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

Gavin F. Painter, Simon J. A. Grove, Ian H. Gilbert, Andrew B. Holmes, Paul R. Raithby, Malcolm L. Hill, Phillip T. Hawkins, Leonard R. Stephens

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    55 Citations (Scopus)

    Abstract

    The D-3-phosphorylated myo-inositol phospholipids PtdIns(3)P, PtdIns(3,4)P-2, PtdIns(3,4,5)P-3 and Ptdins(3,5)P-2 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.

    Original languageEnglish
    Pages (from-to)923-935
    Number of pages13
    JournalJournal of the Chemical Society - Perkin Transactions 1
    Issue number8
    DOIs
    Publication statusPublished - 21 Apr 1999

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