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

doi:10.1039/a900278b

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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Abstract

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 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 - 1999

ASJC Scopus subject areas

General Chemistry

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10.1039/a900278b

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title = "General synthesis of 3-phosphorylated mj'o-inositol phospholipids and derivatives",

abstract = "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.",

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

year = "1999",

doi = "10.1039/a900278b",

language = "English",

pages = "923--935",

journal = "Journal of the Chemical Society - Perkin Transactions 1",

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TY - JOUR

T1 - General synthesis of 3-phosphorylated mj'o-inositol phospholipids and derivatives

AU - Painter, Gavin F.

AU - Grove, Simon J.A.

AU - Gilbert, Lan H.

AU - Holmes, Andrew B.

AU - Raithby, Paul R.

AU - Hill, Malcolm L.

AU - Hawking, Phillip T.

AU - Stephens, Leonard R.

PY - 1999

Y1 - 1999

N2 - 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.

AB - 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.

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DO - 10.1039/a900278b

M3 - Article

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JO - Journal of the Chemical Society - Perkin Transactions 1

JF - Journal of the Chemical Society - Perkin Transactions 1

IS - 8

ER -

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

Abstract

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