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

被引：51

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

页码：923 / 935

页数：13

共 40 条

[1] THE ABSOLUTE-CONFIGURATION OF (+)-1,2,4,5,6-PENTA-O-BENZYL-MYO-INOSITOL [J].