The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative kinetic, spectroscopic, and theoretical assessments of solvent structures and their interactions with reaction intermediates. 96-54-8, Name is 1-Methyl-1H-pyrrole, molecular formula is C5H7N, belongs to pyrrolines compound, is a common compound. In a patnet, author is Chen, LJ, once mentioned the new application about 96-54-8, Quality Control of 1-Methyl-1H-pyrrole.
Characterization of amino acid on glutathione adducts of cis-2-butene-1,4-dial, a reactive metabolite of furan
Metabolic activation of the hepatocarcinogen furan yields metabolites that react covalently with proteins, cis-2-Butene-1,4-dial is a microsomal metabolite of furan, This reactive aldehyde is thought to be the toxic metabolite that is responsible for the carcinogenic activity of furan. In order to characterize the chemistry by which this unsaturated dialdehyde could alkylate proteins, the products formed upon reaction of cis-2-butene-1,4-dial with model nucleophiles in PH 7.4 buffer were investigated, N-alpha-Acetyl-L-cysteine (AcCys) reacts with cis-2-butene-1,4-dial to form N-substituted pyrrolin-2-one adducts. N-Acetyl-L-cysteine (AcCys) reacts rapidly with cis-2-butene-1,4-dial to form multiple uncharacterized products. The inclusion of AcLys in this reaction mixture yielded an N-substituted 3-(S-acetylcysteinyl)pyrrole adduct which Links the two amino acid residues. Related compounds were isolated when cis-2-butene-1,4-dial and glutathione (GSH) were combined. In this case, cis-2-butene-1,4-dial cross-linked two molecules of GSH resulting in either cyclic or acyclic adducts depending on the relative GSH concentration. Incubation of furan with rat liver microsomes in the presence of [glycine-2-H-3]GSH led to the formation of radioactive peaks that coeluted with synthetic standards for the bisgluthathione conjugates. These studies demonstrate that the reactive cis-2-butene-1,4-dial formed during the microsomal oxidation of furan reacts rapidly and completely with amino acid residues to farm pyrrole and pyrrolin-2-one derivatives. Therefore, this metabolite is a likely candidate for the activated furan derivative that binds to proteins. The ease with which cis-2-butene-1,4-dial cross-links amino acids suggests that pyrrole-thiol cross-links may be involved in the toxicity observed following furan exposure.
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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem