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

被引:27
作者
Charon, L [1 ]
Pale-Grosdemange, C [1 ]
Rohmer, M [1 ]
机构
[1] Univ Strasbourg, CNRS, Inst Le Bel, F-67070 Strasbourg, France
关键词
D O I
10.1016/S0040-4039(99)01531-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Zymomonas mobilis synthesizes triterpenoids of the hopane series via the methylerythritol phosphate (MEP) pathway. Owing to the peculiar metabolic pathways in this bacterium, [1-H-2]glucose is the appropriate substrate for generating in vivo deuterium labeled NADP(2)H. After feeding of Z. mobilis with [1-H-2]glucose, deuterium labeling was found on all carbon atoms derived from C-2 and C-4 of isopentenyl diphosphate. The deuterium at C-4 arose from the NADPH dependent reduction catalyzed by the reducto-isomerase converting I-deoxy-D-xylulose 5-phosphate into 2-C-methyl-D-erythritol 4-phosphate. The deuterium at C-2 resulted from an additional reduction at a yet undetermined steps of the MEP biosynthetic pathway. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7231 / 7234
页数:4
相关论文
共 27 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]   Terpenoid biosynthesis from 1-deoxy-D-xylulose in higher plants by intramolecular skeletal rearrangement [J].
Arigoni, D ;
Sagner, S ;
Latzel, C ;
Eisenreich, W ;
Bacher, A ;
Zenk, MH .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1997, 94 (20) :10600-10605
[4]   NMR-STUDIES OF [1-H-2]GLUCOSE METABOLISM IN ZYMOMONAS-MOBILIS [J].
BARROW, KD ;
ROGERS, PL ;
SMITH, GM .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1986, 157 (01) :195-202
[5]  
BRINGERMEYER S, 1988, FEMS MICROBIOL LETT, V54, P131
[6]  
Broers STJ, 1994, THESIS EIDGENOSSISCH
[7]   STEREOCHEMICAL STUDIES OF ISOPRENOID BIOSYNTHESIS - BIOSYNTHESIS OF PENTALENOLACTONE FROM [U-C-13(6)]GLUCOSE AND [6-H-2(2)]GLUCOSE [J].
CANE, DE ;
ROSSI, T ;
TILLMAN, AM ;
PACHLATKO, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (07) :1838-1843
[8]   1-DEOXY-D-THREO-2-PENTULOSE - THE PRECURSOR OF THE 5-CARBON CHAIN OF THE THIAZOLE OF THIAMINE [J].
DAVID, S ;
ESTRAMAREIX, B ;
FISCHER, JC ;
THERISOD, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (24) :7341-7342
[9]   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
[10]   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