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

doi:10.1039/A900278B

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

Research output: Contribution to journal › Article › peer-review

56 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 language	English
Pages (from-to)	923-935
Number of pages	13
Journal	Journal of the Chemical Society - Perkin Transactions 1
Issue number	8
DOIs	https://doi.org/10.1039/A900278B
Publication status	Published - 21 Apr 1999

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title = "General synthesis of 3-phosphorylated myo-inositol phospholipids and derivatives",

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.",

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

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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

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JO - Journal of the Chemical Society - Perkin Transactions 1

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

Abstract

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