80640-14-8

Upstream product

• 87-91-2 diethyl (2R,3R)-tartrate 
• 64-19-7 acetic acid 
• 74213-60-8 diethyl (2R,3S)-erythro-2-acetoxy-3-bromosuccinate 
• 64-17-5 ethanol 
• 74243-84-8 (2S,3S)-2-Bromo-3-hydroxy-succinic acid 

Downstream Products

• 7554-28-1 diethyl (R)-malate 
• 1448429-41-1 (2R,3R) ethyl-3-(1-(4-(4-fluorophenyl)thiazol-2-ylamino)-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl-carbamoyl)oxirane-2-carboxylate 
• 1448429-34-2 (2R,3R)-ethyl 3-((S)-1-(4-(4-fluorophenyl)thiazol-2-ylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylate 
• 1448429-32-0 (2R,3R)-ethyl 3-((S)-1-(2,6-difluorophenylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylate 
• 93061-20-2 (-)-(2R,3R)-trans-Oxiran-2,3-dicarbonsaeure-monoethylester 
• 74243-85-9 trans-2,3-bis(ethoxycarbonyl)oxirane 

Relevant academic research and scientific papers

Harnessing Additional Capability from in Water Reaction Conditions: Aldol versus Knoevenagel Chemoselectivity

Aldol reaction chemoselectivity, racemic or enantioselective, has not been previously demonstrated in the presence of Knoevenagel active functional groups. Here, we show that unhindered β-diketones remain unreacted while a ketone moiety undergoes a highly

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.

Thiirane and michael acceptor compounds and their medical use

The present invention relates to thiirane or Michael acceptor compounds, including the compounds of formula (I) as described and defined herein, and pharmaceutical compositions comprising these compounds, as well as their medical use, particularly their u

3-Fluoroaspartate and pyruvoyl-dependant aspartate decarboxylase: Exploiting the unique characteristics of fluorine to probe reactivity and binding

Fluorine-containing amino acids have been used with great success as mechanism-based inhibitors of pyridoxal phosphate (PLP)-dependent enzymes, and the influence of fluorine on the conformation of molecules has also been extensively studied and practically exploited. In this study, we sought to use these unique characteristics to probe the reactivity and binding of aspartate decarboxylase (ADC) enzymes, which are members of the small class of pyruvoyl-dependant decarboxylases. Since ADC activity has been shown to be essential to the virulence of Mycobacterium tuberculosis, information gained in this manner could be used for the development of inhibitors that selectively target pyruvoyl-dependent enzymes such as ADC, without affecting PLP-dependent enzymes in the host. For this purpose, we synthesized the L-erythro and L-threo isomers of 3-fluoroaspartate and tested their ability to act as substrates and/or inhibitors of the M. tuberculosis and Escherichia coli ADC enzymes. Trapping and MS-based binding analysis was additionally used to confirm that both isomers enter the enzymes' active sites. Our studies show that both isomers undergo single turnover decarboxylation and fluorine elimination reactions to give enamine products that can be trapped within the active site. Interestingly, the enamine/ADC complex that forms from the lerythro (but not the L-threo) isomer is sufficiently stable that it can be observed even without any trapping. This finding suggests that the two 3-fluoroaspartates maintain different conformations within the ADC active site, which leads to the enamine products with configurations of different stabilities. Taken together, our results provide new insights for the development of cofactor-specific inhibitors, and confirm the utility of fluorine as a unique tool for probing reactivity and binding profiles within enzymes.

Synthesis and biophysical studies on 35-Deoxy amphotericin b methyl ester

The use of molecular editing in the elucidation of the mechanism of action of amphotericin B is presented. A modular strategy for the synthesis of amphotericin B and its designed analogues is developed, which relies on an efficient gram-scale synthesis of various subunits of amphotericin B. A novel method for the coupling of the mycosa-mine to the aglycone was identified. The implementation of the approach has enabled the preparation of 35-deoxy amphotericin B methyl ester. Investigation of the antifungal activity and efflux-inducing ability of this amphotericin B congener provided new clues to the role of the 35-hydroxy group and is consistent with the involvement of double barrel ion channels in causing electrolyte efflux. 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

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

Base promoted isomerization of aziridinyl ethers: a new access to alpha- and beta-amino acids.

Aziridinyl ethers are selectively and easily converted to either amino vinyl ethers or alkoxy allylamines by treatment with mixed metal bases (superbases).

A convenient synthesis of optically pure (2R, 3R)-2, 3-epoxysuccinyl - Dipeptides

(2R,3R)-trans-Epoxysuccinyl-dipeptides (7a-7d) were synthesized by acylation of dipeptides with the N-hydroxysuccinimide or pentafluorophenyl ester of monoethyl (2R,3R)-trans-epoxysuccinate (6a-6b). A nucleophilic oxirane ring opening by N-hydroxysuccinimide and pentafluorophenol during the preparation of the active esters could not be observed. Subsequent saponification of the monoethyl ester 7a-7d with KOH in ethanolic solution allowed to produce the dipeptide derivatives as potassium salts (8a-8d) which were found to be stable on storage in the cold. The attempts to convert (2R,3R)-trans-epoxysuccinyl-glycyl-proline (7a) into the corresponding (2S,3S)-trans-epithiosuccinyl derivative via an oxygen sulfur exchange reaction with 3-methylbenzothiazole-2-thione failed completely as among the various products of unknown nature formed only the desulfurated fumaryl derivative could be isolated and characterized.