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

TY - JOUR

T1 - General synthesis of 3-phosphorylated myo-inositol phospholipids and derivatives

AU - Painter, Gavin F.

AU - Grove, Simon J. A.

AU - Gilbert, Ian H.

AU - Holmes, Andrew B.

AU - Raithby, Paul R.

AU - Hill, Malcolm L.

AU - Hawkins, Phillip T.

AU - Stephens, Leonard R.

PY - 1999/4/21

Y1 - 1999/4/21

N2 - 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.

AB - 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.

U2 - 10.1039/A900278B

DO - 10.1039/A900278B

M3 - Article

SN - 0300-922X

SP - 923

EP - 935

JO - Journal of the Chemical Society - Perkin Transactions 1

JF - Journal of the Chemical Society - Perkin Transactions 1

IS - 8

ER -