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

被引：50
|
作者：
Painter, GF
Grove, SJA
Gilbert, IH
Holmes, AB
Raithby, PR
Hill, ML
Hawkins, PT
Stephens, LR
机构：
[1] Univ Cambridge, Dept Chem, Cambridge Ctr Mol Recognit, Cambridge CB2 1EW, England
[2] Univ Cambridge, Dept Chem, Melville Lab, Cambridge CB2 3RA, England
[3] GlaxoWellcome, Med Res Ctr, Stevenage SG1 2NY, Herts, England
[4] Babraham Inst, Dept Signalling, Inositide Lab, Cambridge CB2 4AT, England
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 08期
关键词：
D O I：
10.1039/a900278b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：923 / 935
页数：13
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