23057-98-9

Usage

Uses

Used in Pharmaceutical Research and Development:
DIMETHYL FUMARATE-2,3-D2 is used as a research compound for studying drug metabolism and the development of new pharmaceuticals. Its deuterated nature provides insights into the behavior of the compound in biological systems, aiding in the understanding of its therapeutic effects and potential side effects.
Used in Nuclear Magnetic Resonance (NMR) Spectroscopy:
In the field of analytical chemistry, DIMETHYL FUMARATE-2,3-D2 is utilized as a reagent in NMR spectroscopy for the detailed analysis of the chemical structure and dynamics of molecules. The deuteration enhances the spectral resolution and provides clearer insights into molecular interactions, which is crucial for the elucidation of molecular mechanisms and the optimization of drug candidates.
Used in Multiple Sclerosis Treatment Research:
Although primarily a research tool, DIMETHYL FUMARATE-2,3-D2 also contributes to the ongoing research into the treatment of multiple sclerosis. Its application in this field helps scientists to better understand the disease's pathology and to develop more effective therapies.

Upstream product

• 762-42-5 dimethyl acetylenedicarboxylate 
• 41411-75-0 Dimethyl <2,3-2H2>maleate 
• 67-56-1 methanol 
• 24461-32-3 2,3-[²H₂]-fumaric acid 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 

Downstream Products

• 24461-32-3 2,3-[²H₂]-fumaric acid 
• 1356832-80-8 C₂₀H₁₇⁽²⁾H₂NO₇S 

Relevant academic research and scientific papers

New insight into the pyruvate decarboxylase-catalysed formation of lactaldehyde from H-D exchange experiments: A 'water proof' active site

Pyruvate decarboxylase from Saccharomyces cerevisiae catalyses the formation of lactaldehyde from sodium glyoxylate and acetaldehyde. By using deuteriated sodium glyoxylate (sodium [2-2H]glyoxylate monohydrate) as a substrate it was verified that the lactaldehyde formed retains the deuterium atom. The implications of the observed result for the enzyme mechanism are discussed in the light of conclusions derived from recent molecular modelling studies.

Isoquinolinium N-arylimides and electron-deficient ethylene derivatives

The 1,3-cycloadditions of isoquinolinium N-phenylimide (2a) and N-(2-pyridyl)imide (2b) to twelve α,β-unsaturated carboxylic esters and nitriles proceeded at room temp, with high yields; the reactions furnished tetrahydropyrazolo[5,1-α]isoquinoline derivatives and could be visually followed by the loss of the red color, in this class of azomethine imines, the imide nitrogen of 2 is the nucleophilic center which determines the regiochemistry of the additions to methyl acrylate, acrylonitrile, and their α-methyl and α-chloro derivatives. The diastereoselectivity is low; pairs of adducts were also formed with dimethyl fumarate and maleate. The configurations were elucidated by 1H NMR analysis, which likewise provided the clue to the favored conformation of the tricyclic system. The N-arylimides 5 do not react with ethylene, but the formal ethylene adducts were accessible from the cycloadducts of 5a,b to triphenylvmylphosphoniurn bromide by alkaline cleavage. The statistical analysis of the δH values of 39 cycloadducts provided a consistent set of substituent increments for the pyrazolidine protons.

A Highly Efficient and Large-Scale Synthesis of (2S,3S)-- and (2S,3R)-Aspartic Acids via an Immobilized Aspartase-Containing Microbial Cell System

This paper describes the preparation and utilization of an immobilized aspartase-containing Escherichia coli system for the large-scale synthesis of (2S,3S)-- and (2S,3R)-aspartic acids from the appropriately labeled fumaric acids in >95percent isolated yield, with >97percent deuterium incorporation at the C-3 center and optically pure at both the C-2 and C-3 centers.

Direct Deuteration of Acrylic and Methacrylic Acid Derivatives Catalyzed by Platinum on Carbon in Deuterium Oxide

The platinum on carbon (Pt/C)-catalyzed deuteration of acrylic and methacrylic acid derivatives in deuterium oxide (D2O) efficiently proceeded to give the corresponding acrylic acid-d3 and methacrylic acid-d5 derivatives. The olefinic functionality, as well as the methyl group on the unsaturated functionality of the substrate, were satisfactorily deuterated via the hydrogen (H)-deuterium (D) exchange reaction. The obtained deuterated compounds are useful building blocks and efficiently converted to the corresponding desired products including a polymer without the degradation of the original deuterium contents. (Figure presented.).

Deuterium Substituted Fumarate Derivatives

Provided is a compound of formula (I): or a pharmaceutically acceptable salt thereof. Also provided is a method of activating the Nrf2 pathway, comprising contacting cells with a sufficient amount of a compound of formula (I) described herein. Also provided is a method of treating a neurodegenerative disease, comprising administering to a subject in need of treatment for the neurodegenerative disease an effective amount of a compound of formula (I) described herein.

Synthesis of (2S)-O-phosphohomoserine and its C-2 deuteriated and C-3 chirally deuteriated isotopomers: Probes for the pyridoxal phosphate-dependent threonine synthase reaction

A short efficient synthesis of the threonine synthase substrate (2S)-O-phosphohomoserine and its C-2 deuteriated and C-3 chirally deuteriated isotopomers is described. The synthetic route also provides access to (2S)-homoserine and its C-2 deuteriated and C-3 chirally deuteriated isotopomers in high yield. Preliminary deuterium isotope effect determinations performed using the deuteriated (2S)-O-phosphohomoserines and threonine synthase from E. coli indicate that the removal of protons from both C-2 and C-3 is kinetically important.

Chemistry in Water - Part VI. Catalytic Isomerization and Stereochemistry of Reduction of Acetylenics Mediated by Water-Soluble Phosphines

Reaction of water-soluble phosphines with disubstituted electrodeficient alkynes in H2O (D2O) gives rise either to mixtures of cis and trans (dideuterated) olefins or specifically to trans (dideuterated) olefins, by simple control of the phosphine amount.A cis-trans olefin isomerization catalyzed by sulfonated phosphines occurs in water and allows the obtention of specifically trans disubstituted alkenes from the corresponding cis isomers.