Elucidation of the 2-C-methyl-D-erythritol 4-phosphate pathway for isoprenoid biosynthesis:: straightforward syntheses of enantiopure 1-deoxy-D-xylulose from pentose derivatives

被引:9
作者
Hoeffler, JF [1 ]
Grosdemange-Billiard, C [1 ]
Rohmer, M [1 ]
机构
[1] Univ Strasbourg 1, CNRS, Inst Le Bel, F-67070 Strasbourg, France
关键词
1-deoxy-D-xylulose; methylerythritol phosphate; biosynthesis; isoprenoids; 2-C-methyl-D-erythritol phosphate; terpenoids;
D O I
10.1016/S0040-4039(01)00376-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Optically pure I-deoxy-D-xylulose, a key metabolite for feeding experiments in the methylerythritol phosphate pathway for isoprenoid biosynthesis, is conveniently synthesised from 1,2-O-isopropylidene-alpha -D-xylofuranose or from D-arabinose. This renders labelling with hydrogen isotopes possible. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3065 / 3067
页数:3
相关论文
共 28 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]   Synthesis of 1-deoxy-D-xylulose and 1-deoxy-D-xylulose-5-phosphate [J].
Blagg, BSJ ;
Poulter, CD .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05) :1508-1511
[3]   Deuterium-labelled isotopomers of 2-C-methyl-D-erythritol as tools for the elucidation of the 2-C-methyl-D-erythritol 4-phosphate pathway for isoprenoid biosynthesis [J].
Charon, L ;
Hoeffler, JF ;
Pale-Grosdemange, C ;
Lois, LM ;
Campos, N ;
Boronat, A ;
Rohmer, M .
BIOCHEMICAL JOURNAL, 2000, 346 :737-742
[4]   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
[5]   The chemistry of trichlorosilyl enolates. 8. Highly 1,4-syn diastereoselective, phosphoramide-catalyzed aldol additions of chiral methyl ketone enolates [J].
Denmark, SE ;
Stavenger, RA .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9524-9527
[6]   The deoxyxylulose phosphate pathway of terpenoid biosynthesis in plants and microorganisms [J].
Eisenreich, W ;
Schwarz, M ;
Cartayrade, A ;
Arigoni, D ;
Zenk, MH ;
Bacher, A .
CHEMISTRY & BIOLOGY, 1998, 5 (09) :R221-R233
[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]   New and efficient synthetic routes to 1-deoxy-D-xylulose [J].
Giner, JL .
TETRAHEDRON LETTERS, 1998, 39 (17) :2479-2482
[9]   Escherichia coli open reading frame 696 Is idi, a nonessential gene encoding isopentenyl diphosphate isomerase [J].
Hahn, FM ;
Hurlburt, AP ;
Poulter, CD .
JOURNAL OF BACTERIOLOGY, 1999, 181 (15) :4499-4504
[10]   Chemical synthesis of enantiopure 2-C-methyl-D-erythritol 4-phosphate, the key intermediate in the mevalonate-independent pathway for isoprenoid biosynthesis [J].
Hoeffler, JF ;
Pale-Grosdemange, C ;
Rohmer, M .
TETRAHEDRON, 2000, 56 (11) :1485-1489