Stereochemistry of the reduction step mediated by recombinant 1-deoxy-D-xylulose 5-phosphate isomeroreductase

被引：51

作者：

Proteau, PJ ^{[1
]}

Woo, YH ^{[1
]}

Williamson, RT ^{[1
]}

Phaosiri, C ^{[1
]}

机构：

[1] Oregon State Univ, Coll Pharm, Corvallis, OR 97331 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 06期

关键词：

D O I：

10.1021/ol990839n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The stereochemistry of the 1-deoxy-D-xylulose 5-phosphate (DXP) isomeroreductase reduction step has been examined using the recombinant enzyme from Synechocystis sp. PCC6803, Using [3-H-2]DXP and [4S-H-2]NADPH, it has been determined that the C1 pro-S hydrogen in the 2-C-methyl-D-erythritol 4-phosphate product derives from C3 of DXP, indicating that hydride attack occurs on the re face of the intermediate aldehyde, The 4S-hydride from NADPH is delivered, assigning this enzyme as a class B dehydrogenase.

引用

页码：921 / 923

页数：3

共 13 条

[1] 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

[2] Stereochemical course of the reduction step in the formation of 2-C-methylerythritol from the terpene precursor 1-deoxyxylulose in higher plants [J].

Arigoni, D ;

Giner, JL ;

Sagner, S ;

Wungsintaweekul, J ;

Zenk, MH ;

Kis, K ;

Bacher, A ;

Eisenreich, W .

CHEMICAL COMMUNICATIONS, 1999, (12) :1127-1128

[3] 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

[4] New and efficient synthetic routes to 1-deoxy-D-xylulose [J].

Giner, JL .

TETRAHEDRON LETTERS, 1998, 39 (17) :2479-2482

[5] A METHOD OF PREPARATION AND PURIFICATION OF (4R)-DEUTERATED-REDUCED NICOTINAMIDE ADENINE-DINUCLEOTIDE PHOSPHATE [J].

JEONG, SS ;

GREADY, JE .

ANALYTICAL BIOCHEMISTRY, 1994, 221 (02) :273-277

[6] The stereospecificity of hydrogen transfer to NAD(P)(+) catalyzed by lactol dehydrogenases [J].

Mostad, SB ;

Helming, HL ;

Groom, C ;

Glasfeld, A .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1997, 233 (03) :681-686

[7] Probing the non-mevalonate pathway to phytol in the cyanobacterium Synechocystis sp. UTEX 2470 using deuterium-labeled glucose [J].

Proteau, PJ .

TETRAHEDRON LETTERS, 1998, 39 (51) :9373-9376

[8] ISOPRENOID BIOSYNTHESIS IN BACTERIA - A NOVEL PATHWAY FOR THE EARLY STEPS LEADING TO ISOPENTENYL DIPHOSPHATE [J].

ROHMER, M ;

KNANI, M ;

SIMONIN, P ;

SUTTER, B ;

SAHM, H .

BIOCHEMICAL JOURNAL, 1993, 295 :517-524

[9] Identification of a thiamin-dependent synthase in Escherichia coli required for the formation of the 1-deoxy-D-xylulose 5-phosphate precursor to isoprenoids, thiamin, and pyridoxol [J].

Sprenger, GA ;

Schorken, U ;

Wiegert, T ;

Grolle, S ;

deGraaf, AA ;

Taylor, SV ;

Begley, TP ;

BringerMeyer, S ;

Sahm, H .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1997, 94 (24) :12857-12862

[10] One-dimensional NOE experiments using pulsed field gradients [J].

Stott, K ;

Keeler, J ;

Van, QN ;

Shaka, AJ .

JOURNAL OF MAGNETIC RESONANCE, 1997, 125 (02) :302-324

← 1 2 →