General synthesis of 3-phosphorylated mj'o-inositol phospholipids and derivatives

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

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56 Citations (SciVal)


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.

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

ASJC Scopus subject areas

  • Chemistry(all)


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