Synthesis of 1D-3-deoxy- and -2,3-dideoxyphosphatidylinositol

被引：14

作者：

Kozikowski, AP ^{[1
]}

Qiao, LX ^{[1
]}

Tuckmantel, W ^{[1
]}

Powis, G ^{[1
]}

机构：

[1] ARIZONA CANC CTR, TUCSON, AZ 85724 USA

来源：

TETRAHEDRON | 1997年 / 53卷 / 44期

关键词：

D O I：

10.1016/S0040-4020(97)10003-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both 1D-3-deoxy- and -2,3-dideoxyphosphatidylinositol (3 and 18) were synthesized using the regioisomeric mixture of viburnitol 1,2:4,5- and 1,2:5,6- diacetonides as starting material. Selective acidic hydrolysis and subsequent benzylation or deoxygenation afforded 11a,b as important intermediates. Compound 3 and 18 were of interest as putative antimetabolites of phosphatidylinositol-3-phosphate and as inhibitors of cancer cell colony formation. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：14903 / 14914

页数：12

相关论文

共 33 条

[1] A unified approach to unambiguous synthesis of the phosphatidylinositol-3-phosphates involved in intracellular signal transduction [J].

Aneja, SG ;

Parra, A ;

Stoenescu, C ;

Xia, WY ;

Aneja, R .

TETRAHEDRON LETTERS, 1997, 38 (05) :803-806

[2] A SIMPLE AND EFFECTIVE CHEMICAL PHOSPHORYLATION PROCEDURE FOR BIOMOLECULES [J].

BANNWARTH, W ;

TRZECIAK, A .

HELVETICA CHIMICA ACTA, 1987, 70 (01) :175-186

[3] INSITU ACTIVATION OF BIS-DIALKYLAMINOPHOSPHINES - A NEW METHOD FOR SYNTHESIZING DEOXYOLIGONUCLEOTIDES ON POLYMER SUPPORTS [J].

BARONE, AD ;

TANG, JY ;

CARUTHERS, MH .

NUCLEIC ACIDS RESEARCH, 1984, 12 (10) :4051-4061

[4] A SIMPLE AND EFFICIENT PREPARATION OF DEOXYNUCLEOSIDE PHOSPHORAMIDITES INSITU [J].

BEAUCAGE, SL .

TETRAHEDRON LETTERS, 1984, 25 (04) :375-378

[5] INOSITOL PHOSPHATES AND CELL SIGNALING [J].

BERRIDGE, MJ ;

IRVINE, RF .

NATURE, 1989, 341 (6239) :197-205

[6] INOSITOL TRISPHOSPHATE AND CALCIUM SIGNALING [J].

BERRIDGE, MJ .

NATURE, 1993, 361 (6410) :315-325

[7]

Bruzik K S, 1994, Bioorg Med Chem, V2, P49, DOI 10.1016/S0968-0896(00)82002-7

[8] PROTEIN-KINASE-B (C-AKT) IN PHOSPHATIDYLINOSITOL-3-OH INASE SIGNAL-TRANSDUCTION [J].

BURGERING, BMT ;

COFFER, PJ .

NATURE, 1995, 376 (6541) :599-602

[9] PHOSPHOINOSITIDE KINASES [J].

CARPENTER, CL ;

CANTLEY, LC .

BIOCHEMISTRY, 1990, 29 (51) :11147-11156

[10] Phosphoinositide kinases [J].

Carpenter, CL ;

Cantley, LC .

CURRENT OPINION IN CELL BIOLOGY, 1996, 8 (02) :153-158

← 1 2 3 4 →