Synthesis of [3,5,5,5-2H4]-2-C-methyl-D-erythritol, a substrate designed for the elucidation of the mevalonate independent route for isoprenoid biosynthesis

被引:9
作者
Charon, L [1 ]
Hoeffler, JF [1 ]
Pale-Grosdemange, C [1 ]
Rohmer, M [1 ]
机构
[1] Univ Strasbourg, CNRS, Inst Le Bel, F-67070 Strasbourg, France
关键词
biosynthesis; deuterium labeling; 2-C-methyl-D-erythritol; isoprenoids;
D O I
10.1016/S0040-4039(99)01769-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-C-Methyl-D-erythritol 4-phosphate is a key intermediate in the mevalonate independent pathway for isoprenoid biosynthesis. In order to investigate the fate of the protons in this metabolic route, [3,5,5,5-H-2(4)]-2-C-methyl-D-erythritol was synthesized. The relevant steps allowing deuterium introduction were a palladium(II)-catalyzed hydrostannation and a coupling reaction between a vinyl iodide and a methylcyanocuprate. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8369 / 8373
页数:5
相关论文
共 26 条
[1]  
[Anonymous], 1999, COMPREHENSIVE NATURA, DOI DOI 10.1016/B978-0-08-091283-7.00043-6
[2]   Dimethylallyl pyrophosphate is not the committed precursor of isopentenyl pyrophosphate during terpenoid biosynthesis from 1-deoxyxylulose in higher plants [J].
Arigoni, D ;
Eisenreich, W ;
Latzel, C ;
Sagner, S ;
Radykewicz, T ;
Zenk, MH ;
Bacher, A .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (04) :1309-1314
[3]   On the reduction steps in the mevalonate independent 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway for isoprenoid biosynthesis in the bacterium Zymomonas mobilis [J].
Charon, L ;
Pale-Grosdemange, C ;
Rohmer, M .
TETRAHEDRON LETTERS, 1999, 40 (40) :7231-7234
[4]  
CHAUDHARY SK, 1979, TETRAHEDRON LETT, P99
[5]   Incorporation of 2-C-methyl-D-erythritol, a putative isoprenoid precursor in the mevalonate-independent pathway, into ubiquinone and menaquinone of Escherichia coli [J].
Duvold, T ;
Cali, P ;
Bravo, JM ;
Rohmer, M .
TETRAHEDRON LETTERS, 1997, 38 (35) :6181-6184
[6]  
DUVOLD T, 1997, THESIS U L PASTEUR S, P39
[7]   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
[8]   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
[9]   Biosynthesis of isoprenoids in Escherichia coli:: Retention of the methyl H-atoms of 1-deoxy-D-xylulose [J].
Giner, JL ;
Jaun, B .
TETRAHEDRON LETTERS, 1998, 39 (44) :8021-8022
[10]   Direct formation of 2-C-methyl-D-erythritol 4-phosphate from 1-deoxy-D-xylulose 5-phosphate by 1-deoxy-D-xylulose 5-phosphate reductoisomerase, a new enzyme in the non-mevalonate pathway to isopentenyl diphosphate [J].
Kuzuyama, T ;
Takahashi, S ;
Watanabe, H ;
Seto, H .
TETRAHEDRON LETTERS, 1998, 39 (25) :4509-4512