The synthesis of 1-fluoro- and 1,1-difluoro- analogues of 1-deoxy-D-xylulose

被引：8

作者：

Bouvet, D ^{[1
]}

O'Hagan, D ^{[1
]}

机构：

[1] Univ Durham, Dept Chem, Sci Labs, Durham DH1 3LE, England

来源：

TETRAHEDRON | 1999年 / 55卷 / 34期

关键词：

D O I：

10.1016/S0040-4020(99)00572-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Deoxy-D-xylulose is a key intermediate in bacterial co-factor biosynthesis. We report the synthesis of the 1-fluoro- and 1,1-difluoro- analogues of 1-deoxy-D-xylulose as potential antimetabolites of bacterial 1-deoxy-D-xylulose metabolism (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：10481 / 10486

页数：6

共 20 条

[1] A NEW SYNTHESIS OF 1-DEOXY-D-THREO-2-PENTULOSE, A BIOSYNTHETIC PRECURSOR TO THE THIAZOLE MOIETY OF THIAMIN [J].

BACKSTROM, AD ;

MCMORDIE, RAS ;

BEGLEY, TP .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1995, 14 (01) :171-175

[2] STEREOCONTROL IN CYCLIZATION OF DIOXOLANYL RADICALS [J].

BATSANOV, AS ;

BEGLEY, MJ ;

FLETCHER, RJ ;

MURPHY, JA ;

SHERBURN, MS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (10) :1281-1294

[3] Ready access to fluorinated phosphonate mimics of secondary phosphates. Synthesis of the (alpha,alpha-difluoroalkyl) phosphonate analogues of L-phosphoserine, L-phosphoallothreonine, and L-phosphothreonine [J].

Berkowitz, DB ;

Eggen, M ;

Shen, QR ;

Shoemaker, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4666-4675

[4] Biosynthesis of vitamin B6:: The oxidation of 4-(phosphohydroxy)-L-threonine by PdxA [J].

Cane, DE ;

Hsiung, YJ ;

Cornish, JA ;

Robinson, JK ;

Spenser, ID .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) :1936-1937

[5] THE BIOSYNTHESIS OF THIAMINE - SYNTHESES OF [1,1,1,5-(H4)-H-2]-1-DEOXY-D-THREO-2-PENTULOSE AND INCORPORATION OF THIS SUGAR IN BIOSYNTHESIS OF THIAZOLE BY ESCHERICHIA-COLI-CELLS [J].

DAVID, S ;

ESTRAMAREIX, B ;

FISCHER, JC ;

THERISOD, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (09) :2131-2137

[6] FLUORO KETONE INHIBITORS OF HYDROLYTIC ENZYMES [J].

GELB, MH ;

SVAREN, JP ;

ABELES, RH .

BIOCHEMISTRY, 1985, 24 (08) :1813-1817

[7] Biosynthesis of isoprenoids in Escherichia coli:: The fate of the 3-H and 4-H atoms of 1-deoxy-d-xylulose [J].

Giner, JL ;

Jaun, B ;

Arigoni, D .

CHEMICAL COMMUNICATIONS, 1998, (17) :1857-1858

[8] Biosynthesis of vitamins B-1 and B-6 in Escherichia coli: Concurrent incorporation of 1-deoxy-D-xylulose into thiamin (B-1) and pyridoxol (B-6) [J].

Himmeldirk, K ;

Kennedy, IA ;

Hill, RE ;

Sayer, BG ;

Spenser, ID .

CHEMICAL COMMUNICATIONS, 1996, (10) :1187-1188

[9] 1-DEOXY-D-XYLULOSE [J].

KENNEDY, IA ;

HEMSCHEIDT, T ;

BRITTEN, JF ;

SPENSER, ID .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1995, 73 (08) :1329-1337

[10] CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].

KOLB, HC ;

VANNIEUWENHZE, MS ;

SHARPLESS, KB .

CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547

← 1 2 →