Stereoselective synthesis of inositol mono, bis and trisphosphate analogues from 6-deoxy-D-inositol precursors.

被引：12

作者：

de Almeida, MV

Dubreuil, D ^{[1
]}

Cleophax, J

Verre-Sebrié, C

Pipelier, M

Prestat, G

Vass, G

Gero, SD

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

[2] Fac Sci & Tech, CNRS UMR 6513, Organ Synth Lab, F-44322 Nantes 03, France

来源：

TETRAHEDRON | 1999年 / 55卷 / 23期

关键词：

D O I：

10.1016/S0040-4020(99)00365-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of opticaly pure deoxy-myo-inositol mono, bis and trisphosphate analogues is described from 4-O-benzyl-2,3-di-O-cyclohexylidene-6-deoxy-myo-inositol and corresponding 1,5 epimer chiro-inositol. These precursors, which derive from galactose, are used to accede to a variety of cyclitol intermediates employing protection/deprotection sequence. The phosphorylation procedure was performed to produce free and original substituted phosphate derivatives aimed to be incorporated through the lipidic cell membrane for in vivo evaluation. (C) 1999 Elsevier Science Ltd. All rights reserved.

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收藏

页码：7251 / 7270

页数：20

相关论文

共 61 条

[1]

[Anonymous], 1993, The inositol phosphates: chemical synthesis and biological significance

[2] IDENTIFICATION OF (1S)-PHOSPHORYLOXY-(2R,4S)-DIHYDROXYCYCLOHEXANE AS A POTENT INHIBITOR OF INOSITOL MONOPHOSPHATASE [J].

BAKER, R ;

LEESON, PD ;

LIVERTON, NJ ;

KULAGOWSKI, JJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (06) :462-464

[3] SYNTHESIS OF 2-DEOXYINOSITOL AND 6-DEOXYINOSITOL 1-PHOSPHATE AND THE ROLE OF THE ADJACENT HYDROXY-GROUPS IN THE MECHANISM OF INOSITOL MONOPHOSPHATASE [J].

BAKER, R ;

KULAGOWSKI, JJ ;

BILLINGTON, DC ;

LEESON, PD ;

LENNON, IC ;

LIVERTON, N .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (18) :1383-1385

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

BERRIDGE, MJ ;

IRVINE, RF .

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

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

BERRIDGE, MJ .

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

[6] INOSITOL TRISPHOSPHATE, A NOVEL 2ND MESSENGER IN CELLULAR SIGNAL TRANSDUCTION [J].

BERRIDGE, MJ ;

IRVINE, RF .

NATURE, 1984, 312 (5992) :315-321

[7] THE TOTAL SYNTHESIS OF MYOINOSITOL PHOSPHATES VIA MYOINOSITOL ORTHOFORMATE [J].

BILLINGTON, DC ;

BAKER, R ;

KULAGOWSKI, JJ ;

MAWER, IM ;

VACCA, JP ;

DESOLMS, SJ ;

HUFF, JR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (08) :1423-1429

[8] RECENT DEVELOPMENTS IN THE SYNTHESIS OF MYOINOSITOL PHOSPHATES [J].

BILLINGTON, DC .

CHEMICAL SOCIETY REVIEWS, 1989, 18 (01) :83-122

[9] COMPARATIVE-STUDIES OF D-MYOINOSITOL 1,4,5-TRISPHOSPHATE AND SYNTHETIC 6-DEOXY D-MYOINOSITOL 1,4,5-TRISPHOSPHATE - BINDING AND CALCIUM RELEASE ACTIVITY IN RAT PAROTID MICROSOMES [J].

BONIS, D ;

SEZAN, A ;

MAUDUIT, P ;

DUBREUIL, D ;

CLEOPHAX, J ;

GERO, SD ;

ROSSIGNOL, B .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1991, 175 (03) :894-900

[10] ENANTIOSELECTIVE SYNTHESIS OF INOSITOLS AS INTERMEDIATES FOR THE PREPARATION OF DEOXY-INOSITOL PHOSPHATES FROM D-GALACTOSE [J].

CLEOPHAX, J ;

DUBREUIL, D ;

GERO, SD ;

LOUPY, A ;

DEALMEIDA, MV ;

DASILVA, AD ;

VASS, G ;

BISCHOFF, E ;

PERZBORN, E ;

HECKER, G ;

LOCKHOFF, O .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (08) :831-834

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