Synthesis of tritium labelled 2-C-methyl-D-erythritol, a useful substrate for the elucidation of the methylerythritol phosphate pathway for isoprenoid biosynthesis

被引:12
作者
Hoeffler, JF [1 ]
Grosdemange-Billiard, C [1 ]
Rohmer, M [1 ]
机构
[1] Univ Louis Pasteur Strasbourg 1, CNRS, Inst Le Bel, F-67070 Strasbourg, France
关键词
biosynthesis; isoprenoids; 2-C-methyl-D-erythritol;
D O I
10.1016/S0040-4039(00)00726-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Free 2-C-methyl-D-erythritol is utilised for isoprenoid biosynthesis by Escherichia coli mutants lacking the two first enzymes of the methylerythritol phosphate pathway, the deoxyxylulose phosphate synthase and isomero-reductase. For feeding experiments, this tetrol was synthesised with an overall 43% yield from readily available 1,2-O-isopropylidene-alpha-D-xylofuranose, including the possibility of tritium labelling. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4885 / 4889
页数:5
相关论文
共 30 条
[1]  
[Anonymous], 1999, COMPREHENSIVE NATURA, DOI DOI 10.1016/B978-0-08-091283-7.00043-6
[2]   2-C-METHYL-ERYTHRITOL, A NEW BRANCHED ALDITOL FROM CONVOLVULUS-GLOMERATUS [J].
ANTHONSEN, T ;
HAGEN, S ;
KAZI, MA ;
SHAH, SW ;
TAGAR, S .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1976, 30 (01) :91-93
[3]   SYNTHETIC AND SPECTROSCOPIC STUDIES OF 2-C-METHYL-ERYTHRITOL AND 2-C-METHYL-THREITOL [J].
ANTHONSEN, T ;
HAGEN, S ;
SALLAM, MAE .
PHYTOCHEMISTRY, 1980, 19 (11) :2375-2377
[4]   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
[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]   Studies on the biosynthesis of taxol: The taxane carbon skeleton is not of mevalonoid origin [J].
Eisenreich, W ;
Menhard, B ;
Hylands, PJ ;
Zenk, MH ;
Bacher, A .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1996, 93 (13) :6431-6436
[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]   PROKARYOTIC HOPANOIDS - THE BIOSYNTHESIS OF THE BACTERIOHOPANE SKELETON - FORMATION OF ISOPRENIC UNITS FROM 2 DISTINCT ACETATE POOLS AND A NOVEL TYPE OF CARBON CARBON LINKAGE BETWEEN A TRITERPENE AND D-RIBOSE [J].
FLESCH, G ;
ROHMER, M .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1988, 175 (02) :405-411
[9]   BRANCHED-CHAIN SUGARS .7. DETERMINATION OF CONFIGURATION OF L-VINELOSE BY SYNTHESIS [J].
FUNABASHI, M ;
YAMAZAKI, S ;
YOSHIMURA, J .
CARBOHYDRATE RESEARCH, 1975, 44 (02) :275-283
[10]   Biosynthesis of terpenoids:: YgbB protein converts 4-diphosphocytidyl-2C-methyl-D-erythritol 2-phosphate to 2C-methyl-D-erythritol 2,4-cyclodiphosphate [J].
Herz, S ;
Wungsintaweekul, J ;
Schuhr, CA ;
Hecht, S ;
Lüttgen, H ;
Sagner, S ;
Fellermeier, M ;
Eisenreich, W ;
Zenk, MH ;
Bacher, A ;
Rohdich, F .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2000, 97 (06) :2486-2490