Chemical synthesis of enantiopure 2-C-methyl-D-erythritol 4-phosphate, the key intermediate in the mevalonate-independent pathway for isoprenoid biosynthesis

被引：29

作者：

Hoeffler, JF ^{[1
]}

Pale-Grosdemange, C ^{[1
]}

Rohmer, M ^{[1
]}

机构：

[1] Univ Louis Pasteur Strasbourg 1, Lab Chim & Biochim Microorganismes, Inst Le Bel, F-67043 Strasbourg, France

来源：

TETRAHEDRON | 2000年 / 56卷 / 11期

关键词：

biosynthesis; isoprenoids; 2-C-methyl-D-erythritol; 4-phosphate;

D O I：

10.1016/S0040-4020(00)00065-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically pure 2-C-methyl-D-erythritol 4-phosphate, a key intermediate in the mevalonate-independent route for isoprenoid biosynthesis, is conveniently synthesized from 1,2-O-isopropylidene-alpha-D-xylofuranose, including the possibility of radiolabeling of this substrate. (C) 2000 Elsevier Science Ltd. All rights reserved.

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收藏

页码：1485 / 1489

页数：5

相关论文

共 22 条

[1]

[Anonymous], 1999, COMPREHENSIVE NATURA, DOI DOI 10.1016/B978-0-08-091283-7.00043-6

[2] BRANCHED-CHAIN SUGARS .1. ALTERNATIVE SYNTHESIS OF 6-DEOXY-3-C-METHYL-2,3,4-TRI-O-METHYL-D-ALLOPYRANOSE [J].

BRIMACOMBE, JS ;

ROLLINS, AJ ;

THOMPSON, SW .

CARBOHYDRATE RESEARCH, 1973, 31 (01) :108-113

[3]

CZERNECKI S, 1990, SYNTHESIS-STUTTGART, V651, P653

[4] Synthesis of ribosylhopane, the putative biosynthetic precursor of bacterial triterpenoids of the hopane series [J].

Duvold, T ;

Rohmer, M .

TETRAHEDRON, 1999, 55 (32) :9847-9858

[5] Biosynthesis of 2-C-methyl-D-erythritol, a putative C-5 intermediate in the mevalonate independent pathway for isoprenoid biosynthesis [J].

Duvold, T ;

Bravo, JM ;

PaleGrosdemange, C ;

Rohmer, M .

TETRAHEDRON LETTERS, 1997, 38 (27) :4769-4772

[6] 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

[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] NUCLEOSIDE POLYPHOSPHATES .2. A SYNTHESIS OF URIDINE-5'-DIPHOSPHATE AND URIDINE-5'-TRIPHOSPHATE [J].

HALL, RH ;

KHORANA, HG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (20) :5056-5060

[9] BENZYL TRICHLOROACETIMIDATE, A VERSATILE REAGENT FOR ACID-CATALYZED BENZYLATION OF HYDROXY-GROUPS [J].

IVERSEN, T ;

BUNDLE, DR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (23) :1240-1241

[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