206440-72-4

Basic information

• Product Name: 2-C-METHYL-D-ERYTHRITOL 4-PHOSPHATE (MEP)
• Synonyms: 2-C-Methyl-D-erythriotl 4-phosphate (MEP);2-C-Methyl-D-erythritol 4-phosphate lithium salt;2-C-METHYL-D-ERYTHRITOL 4-PHOSPHATE (MEP);Methyl-D-erythritol Phosphate
• CAS NO: 206440-72-4
• Molecular Formula: C5H13O7P
• Molecular Weight: 216.126281
• Product Categories: Aliphatics;Chiral Reagents;Enzyme substrates;Phosphorylating and Phosphitylating Agents
• Mol File: 206440-72-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 530.7°C at 760 mmHg
• Flash Point: 274.8°C
• Appearance: /
• Density: 1.668g/cm³
• Vapor Pressure: 1.76E-13mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: ?20°C
• PKA: 1.86±0.10(Predicted)
• CAS DataBase Reference: 2-C-METHYL-D-ERYTHRITOL 4-PHOSPHATE (MEP)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-C-METHYL-D-ERYTHRITOL 4-PHOSPHATE (MEP)(206440-72-4)
• EPA Substance Registry System: 2-C-METHYL-D-ERYTHRITOL 4-PHOSPHATE (MEP)(206440-72-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 206440-72-4(Hazardous Substances Data)

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

• 190079-18-6 Phosphoric acid mono-((2R,3S)-2,3-dihydroxy-4-oxo-pentyl) ester 
• 1005155-51-0 C₃₄H₃₇O₈P 
• 270076-04-5 1,2-O-isopropylidene-3-C-methyl-α-D-ribofuranose 5-dibenzylphosphate 
• 258518-30-8 2,3-O-isopropylidene-2-C-methyl-D-erythrose 4-dibenzyl phosphate 
• 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 
• 257612-05-8 methyl (Z)-4-((tert-butyldimethylsilyl)oxy)-3-methylbut-2-enoate 
• 257612-06-9 (Z)-4-(tert-butyldimethylsilanyloxy)-3-methyl-but-2-en-1-ol 
• 258518-27-3 2,3-O-isopropylidene-2-C-methyl-D-erythrofuranose 
• 18465-72-0 (-)-(2R,3R)-2,3-O-isopropylidene-2-C-methyl-D-erythrono-1,4-lactone 
• 77587-29-2 2-C-methyl-2,3-O-isopropylidene-D-erythritol 
• 931430-94-3 4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-2-C-methyl-D-erythritol 
• 931430-96-5 4-O-benzyl-1-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-2-C-methyl-D-erythritol 

Downstream Products

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

Relevant articles and documents

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

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.

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