80640-15-9

Usage

Uses

Used in Pharmaceutical Industry:
(2R,3R)-diethyl 2-bromo-3-hydroxysuccinate is used as an intermediate in the synthesis of E-64 derivative, which is a potent inhibitor of cathepsins B and L, enzymes involved in various physiological and pathological processes. This makes it a valuable compound in the development of drugs targeting these enzymes for therapeutic purposes.
Additionally, it has potential as an inhibitor of calpain, a family of calcium-activated neutral proteases that play a role in various cellular processes, including cell death, muscle function, and synaptic plasticity. Inhibition of calpain has been implicated in the treatment of various diseases, such as neurodegenerative disorders and muscular dystrophy.

Upstream product

• 87-91-2 diethyl (2R,3R)-tartrate 
• 74213-59-5 diethyl (2S,3R)-erythro-2-acetoxy-3-bromosuccinate 
• 13811-71-7 diethyl (2S,3S)-tartrate 
• 64-19-7 acetic acid 

Downstream Products

• 3291-46-1 (2S,3S)-diethyl oxirane-2,3-dicarboxylate 
• 63734-73-6 ethyl (2S,3S)-2,3-epoxysuccinate 
• 1448429-26-2 (2S,3S)-ethyl-3-((S)-1-((1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)methylamino)-1-oxo-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate 
• 1448429-27-3 (2S,3S)-ethyl-3-((S)-1-((1-(2,6-difluorophenyl)-1H-1,2,3-triazol-4-yl)methylamino)-1-oxo-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate 
• 1448429-28-4 (2S,3S)-ethyl-3-((S)-1-((1-mesityl-1H-1,2,3-triazol-4-yl)methylamino)-1-oxo-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate 
• 1448429-30-8 (2S,3S)-ethyl 3-((S)-4-methyl-1-oxo-1-(phenylamino)pentan-2-ylcarbamoyl)oxirane-2-carboxylate 
• 1448429-31-9 (2S,3S)-ethyl 3-((S)-1-(2,6-difluorophenylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylate 
• 1448429-33-1 (2S,3S)-ethyl 3-((S)-1-(4-(4-fluorophenyl)thiazol-2-ylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylate 
• 1448429-35-3 (2S,3S)-ethyl 3-((S)-1-(4-(4-fluorophenylsulfonamido)butylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylate 
• 1448429-38-6 (2S,3S)-ethyl 3-((S)-3-(1H-imidazol-5-yl)-1-oxo-1-(phenylamino)propan-2-ylcarbamoyl)oxirane-2-carboxylate 
• 1448429-39-7 (2S,3S)-ethyl 3-((S)-3-(1H-imidazol-5-yl)-1-(mesitylamino)-1-oxopropan-2-ylcarbamoyl)oxirane-2-carboxylate 
• 1448429-40-0 (2S,3S)-ethyl 3-(1-(4-(4-fluorophenyl)thiazol-2-ylamino)-3-(1H-imidazol-4-yl)-1-oxopropan-2-ylcarbamoyl)oxirane-2-carboxylate 
• 1448429-44-4 (2S,3S)-ethyl 3-((S)-1-oxo-1-(phenylamino)-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate 
• 1448429-45-5 (2S,3S)-ethyl 3-((S)-1-(4-(4-fluorophenyl)thiazol-2-ylamino)-1-oxo-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate 

Relevant academic research and scientific papers

Approaching an experimental electron density model of the biologically active trans-epoxysuccinyl amide group—Substituent effects vs. crystal packing

The trans-epoxysuccinyl amide group as a biologically active moiety in cysteine protease inhibitors such as loxistatin acid E64c has been used as a benchmark system for theoretical studies of environmental effects on the electron density of small active i

Cysteine protease inhibitors and uses thereof

The invention provides for novel cysteine protease inhibitors and compositions comprising novel cysteine protease derivatives. The invention further provides for methods for treatment of neurodegenerative diseases comprising administration novel cysteine

Design, synthesis, and optimization of novel epoxide incorporating peptidomimetics as selective calpain inhibitors

Hyperactivation of the calcium-dependent cysteine protease calpain 1 (Cal1) is implicated as a primary or secondary pathological event in a wide range of illnesses and in neurodegenerative states, including Alzheimer's disease (AD). E-64 is an epoxide-containing natural product identified as a potent nonselective, calpain inhibitor, with demonstrated efficacy in animal models of AD. By use of E-64 as a lead, three successive generations of calpain inhibitors were developed using computationally assisted design to increase selectivity for Cal1. First generation analogues were potent inhibitors, effecting covalent modification of recombinant Cal1 catalytic domain (Cal1cat), demonstrated using LC-MS/MS. Refinement yielded second generation inhibitors with improved selectivity. Further library expansion and ligand refinement gave three Cal1 inhibitors, one of which was designed as an activity-based protein profiling probe. These were determined to be irreversible and selective inhibitors by kinetics studies comparing full length Cal1 with the general cysteine protease papain.

First asymmetric total synthesis of synerazol, an antifungal antibiotic, and determination of its absolute stereochemistry

By synthesizing two possible diastereomers, the first asymmetric total synthesis of synerazol, an antifungal antibiotic, has been accomplished, allowing determination of its absolute stereochemistry. A more practical second generation route was also estab

An improved preparation of the activity-based probe JPM-OEt and in situ applications

A short, stereoselective synthesis of the general, cell permeable cathepsin probe JPM-OEt, is presented. The synthetic route is improved and described in more detail than previous reports for related compounds. This serves as a facile method for the synth

Stereoselective synthesis of optically active forms of δ-multistriatin, the attractant for european populations of the smaller european elm bark beet

A stereoselective synthesis of highly optically pure enantiomers of δ-multistriatin [(1S,2S,4S,5R)-2,4-dimethyl-5-ethyl-6, 8-dioxabicyclo[3.2.1)octane and its antipode] was accomplished starting from tartaric acid enantiomers.