Synthesis of (E)-4-hydroxydimethylallyl diphosphate.: An intermediate in the methyl erythritol phosphate branch of the isoprenoid pathway

被引:23
作者
Fox, DT [1 ]
Poulter, CD [1 ]
机构
[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
关键词
D O I
10.1021/jo0258453
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The syntheses of (E)-1-hydroxy-2-methyl-2-buten-4-yl diphosphate ((E)-4-hydroxydimethylallyl diphosphate, HDMAPP), an intermediate in the methyl erythritol phosphate pathway, and (E)-[4-H-2]HDMAPP were accomplished in two steps from (E)-4-chloro-2-methyl-2-butenal. The synthetic route is easily adaptable for the facile incorporation of tritium at C-4 of the diphosphate.
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页码:5009 / 5010
页数:2
相关论文
共 17 条
[1]   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
[2]  
Bochar D.A., 1999, Comprehensive Natural Products Chemistry, VVolume 2, P15
[3]  
BUCKINGHAM J, 1998, DICT NATURAL PRODUCT
[4]  
DAVISSON VJ, 1985, METHOD ENZYMOL, V110, P130
[5]  
DAVISSON VJ, 1986, BIOCHEMISTRY-US, V25, P4768
[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]   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
[8]   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
[9]   E-coli MEP synthase:: Steady-state kinetic analysis and substrate binding [J].
Koppisch, AT ;
Fox, DT ;
Blagg, BSJ ;
Poulter, CD .
BIOCHEMISTRY, 2002, 41 (01) :236-243
[10]   Studies on the nonmevalonate pathway:: conversion of 4-(cytidine 5′-diphospho)-2-C-methyl-D-erythritol to its 2-phospho derivative by 4-(cytidine 5′-diphospho)-2-C-methyl-D-erythritol kinase [J].
Kuzuyama, T ;
Takagi, M ;
Kaneda, K ;
Watanabe, H ;
Dairi, T ;
Seto, H .
TETRAHEDRON LETTERS, 2000, 41 (16) :2925-2928