206440-72-4

Usage

Uses

A substrate for terpenoid biosynthesis; terpenoid biosynthesis enzyme Escherichia

InChI:InChI=1/C5H13O7P/c1-5(8,3-6)4(7)2-12-13(9,10)11/h4,6-8H,2-3H2,1H3,(H2,9,10,11)/t4-,5+/m1/s1

Upstream product

• 270076-08-9 2-O-benzyl-2-C-methyl-D-erythritol 4-dibenzylphosphate 
• 18465-72-0 (-)-(2R,3R)-2,3-O-isopropylidene-2-C-methyl-D-erythrono-1,4-lactone 
• 257612-06-9 (Z)-4-(tert-butyldimethylsilanyloxy)-3-methyl-but-2-en-1-ol 
• 257612-05-8 methyl (Z)-4-((tert-butyldimethylsilyl)oxy)-3-methylbut-2-enoate 
• 1005155-51-0 C₃₄H₃₇O₈P 
• 257612-10-5 (2S,3R)-dimethyl 1-(tert-butyldimethylsilyloxy)-2,3-dihydroxy-2-methyl-butan-4-phosphate 
• 257612-08-1 dimethyl 1-(tert-butyldimethylsilyloxy)-2-methyl-buten-4-phosphate 
• 258518-28-4 2,3-O-isopropylidene-2-C-methyl-D-erythrose-(O-benzyl)oxime 
• 258518-27-3 2,3-O-isopropylidene-2-C-methyl-D-erythrofuranose 
• 77587-29-2 2-C-methyl-2,3-O-isopropylidene-D-erythritol 
• 931430-87-4 1-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-2-C-methyl-D-erythritol 
• 931430-93-2 4-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-2-C-methyl-D-erythritol 
• 931431-00-4 Phosphoric acid dibenzyl ester (4R,5S)-5-benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 258518-31-9 2,3-O-isopropylidene-2-C-methyl-D-erythritol 4-dibenzyl phosphate 

Downstream Products

• 263016-94-0 4-diphosphocytidyl-2-C-methylerythritol 

Relevant academic research and scientific papers

Formal synthesis of 4-diphosphocytidyl-2-C-methyl d-erythritol from d-(+)-arabitol

2-C-Methyl-d-erythritol-4-phosphate (MEP) is a key chemical intermediate of the non-mevalonate pathway for isoprenoid biosynthesis employed by many pathogenic microbes. MEP is also the precursor for the synthesis of 4-diphosphocytidyl-2-C-methyl d-erythri

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

1-Deoxy-D-xylulose 5-phosphate is biotransformed to 2-C-methyl-D- erythritol 4-phosphate in a single step in the presence of NADPH by a new recombinant enzyme named 1-deoxy-D-xylulose 5-phosphate reductoisomerase purified from Escherichia coli.

Synthesis of enantiopure 2-C-methyl-d-erythritol-4-phosphate

The synthesis of enantiopure 2-C-methyl-d-erythritol-4-phosphate is disclosed. A 1,3-diol possessing a quaternary stereogenic centre, prepared stereoselectively from an acyclic tri-substituted alkene, has been utilized as a key intermediate.

A convenient synthesis of 2-C-methyl-d-erythritol 4-phosphate and isotopomers of its precursor

A new synthetic approach toward 2-C-methyl-d-erythritol 4-phosphate (MEP), a key intermediate in the mevalonate-independent biosynthetic pathway for isoprenoids, and deuterated analogues of its precursor, 2-C-methyl-d-erythritol acetonide, is described. T

Molecular cloning, expression and characterization of the first three genes in the mevalonate-independent isoprenoid pathway in Streptomyces coelicolor

The mevalonate-independent biosynthetic pathway to isopentenyl diphosphate and dimethylallyl diphosphate, the universal precursors to the isoprenoids, operates in eubacteria, including Escherichia coli, in algae, and in the plastids of higher plants. A search of the Sanger Centre Streptomyces coelicolor genome database revealed open reading frames with ca. 40-50% identity at the deduced amino acid level to the first three E. coli enzymes of this pathway, corresponding to deoxyxylulose phosphate synthase, deoxyxylulose phosphate reductoisomerase and 2-C-methyl erythritol 4-phosphate cytidyltransferase. The coelicolor genes have been cloned and expressed in E. coli, and the recombinant proteins characterized physically and kinetically. The presence of the corresponding enzyme activities in Extracts of S. coelicolor CH999 further supports the operation of the mevalonate-independent pathway in this organism. Copyright

Synthesis of 2-C-Methyl-D-erythritol 4-phosphate: The first pathway-specific intermediate in the methylerythritol phosphate route to isoprenoids

(matrix presented) 2-C-Methyl-D-erythritol 4-phosphate (4), formed from 1-deoxy-D-xylulose 5-phosphate (3), is the first pathway-specific intermediate in the methylerythritol phosphate route for the biosynthesis of isoprenoid compounds in bacteria, algae, and plant chloroplasts. In this report, 4 was synthesized from 1,2-propanediol (7) in seven steps with an overall yield of 32% and in an enantiomeric excess of 78%.

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

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-α-D-xylofuranose, including the possibility of radiolabeling of t

Formation of 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol from 2-C- methyl-D-erythritol 4-phosphate by 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase, a new enzyme in the nonmevalonate pathway

2-C-Methyl,D-erythritol 4-phosphate is transformed to 4-(cytidine 5'- diphospho)-2-C-methyl-D-erythritol in the presence of cytidine 5'- triphosphate by a novel Escherichia coli enzyme, 2-C-methyl-D-erythritol 4- phosphate cytidylyltransferase, involved in the nonmevalonate pathway. (C) 2000 Elsevier Science Ltd.