866879-14-3

Basic information

• Product Name: [4-2H]chorismic acid
• Synonyms: [4-2H]chorismic acid
• CAS NO: 866879-14-3
• Molecular Weight: 227.178
• Mol File: 866879-14-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [4-2H]chorismic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [4-2H]chorismic acid(866879-14-3)
• EPA Substance Registry System: [4-2H]chorismic acid(866879-14-3)

Safety Data

• Hazardous Substances Data: 866879-14-3(Hazardous Substances Data)

Upstream product

• 895558-57-3 ((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl trifluoromethanesulphonate 
• 19139-80-1 ((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol 
• 895560-07-3 2-(Diethoxy-phosphoryl)-3-((3aS,5R,6aR)-2,2-dimethyl-6-oxo-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-propionic acid methyl ester 
• 866879-10-9 methyl 3,4-[4-2H](O-isopropylidene)shikimate 
• 866879-12-1 methyl [4-2H]shikimate 
• 4265-07-0 phospho(enol)pyruvic acid mono potassium salt 
• 866878-98-0 3-((3aS,5R,6R,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(diethoxyphosphoryl)propionic acid methyl ester 
• 866879-04-1 2-(diethoxyphosphoryl)-3-((3aS,5R,6S,6aS,[6-2H])-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)propionic acid methyl ester 
• 866879-01-8 3-((3aS,5R,6R,6aS)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(diethoxyphosphoryl)propionic acid methyl ester 
• 866879-07-4 2-(diethoxyphosphoryl)-3-((3aS,4R,6aS,[3a-2H])-6-hydroxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)propionic acid methyl ester 

Downstream Products

• 89829-47-0 [3-2H]pyruvic acid 

Relevant articles and documents

Isotope effects on the enzymatic and nonenzymatic reactions of chorismate

The important biosynthetic intermediate chorismate reacts thermally by two competitive pathways, one leading to 4-hydroxybenzoate via elimination of the enolpyruvyl side chain, and the other to prephenate by a facile Claisen rearrangement. Measurements with isotopically labeled chorismate derivatives indicate that both are concerted sigmatropic processes, controlled by the orientation of the enolpyruvyl group. In the elimination reaction of [4- 2H]chorismate, roughly 60% of the label was found in pyruvate after 3 h at 60 °C. Moreover, a 1.846 ± 0.057 2H isotope effect for the transferred hydrogen atom and a 1.0374 ± 0.0005 18O isotope effect for the ether oxygen show that the transition state for this process is highly asymmetric, with hydrogen atom transfer from C4 to C9 significantly less advanced than C-O bond cleavage. In the competing Claisen rearrangement, a very large 18O isotope effect at the bond-breaking position (1.0482 ± 0.0005) and a smaller 13C isotope effect at the bond-making position (1.0118 ± 0.0004) were determined. Isotope effects of similar magnitude characterized the transformations catalyzed by evolutionary unrelated chorismate mutases from Escherichia coli and Bacillus subtilis. The enzymatic reactions, like their solution counterpart, are thus concerted [3,3]-sigmatropic processes in which C-C bond formation lags behind C-O bond cleavage. However, as substantially larger 18O and smaller 13C isotope effects were observed for a mutant enzyme in which chemistry is fully rate determining, the ionic active site may favor a somewhat more polarized transition state than that seen in solution.