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- W2073876293 abstract "Protein modification by the neurotoxic gamma-diketone 3-methyl-2,5-hexanedione (3-MHD) and its analogue 3-(trifluoromethyl)-2,5-hexanedione (3-TFMHD) was examined. Unlike 3-MHD, which forms lysine-based pyrroles that lead to autoxidation-dependent protein cross-linking, 3-TFMHD forms an autoxidatively inert pyrrole. The surprising finding that 3-TFMHD was nonetheless as effective as 3-MHD in cross-linking ribonuclease A suggested that protein lysine condensation with 3-TFMHD could take an alternate course competing with pyrrole formation. Model studies using neopentylamine led to the isolation of the expected 1-(2,2-dimethylpropyl)-2,5-dimethyl-3-(trifluoromethyl)pyrrole as well as the neopentylamine-3-TFMHD 2:1 adducts N,N'-bis(2,2-dimethylpropyl)-2-amino-3-acetyl-5-methylpyrrole (major) and N,N'-bis(2,2-dimethylpropyl)-3-(1-aminoethylidene)-5-methyl-4-pyrrolin-2-one (minor). The formation of these 2:1 adducts, the lysine analogues of which are believed to be mainly responsible for the observed protein cross-linking, is proposed to proceed via Schiff base formation, enamine fluoride elimination, second amine condensation, and hydrolysis." @default.
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- W2073876293 date "2002-03-23" @default.
- W2073876293 modified "2023-09-29" @default.
- W2073876293 title "Cross-Linking of Proteins by 3-(Trifluoromethyl)-2,5-hexanedione. Model Studies Implicate an Unexpected Amine-Dependent Defluorinative Substitution Pathway Competing with Pyrrole Formation" @default.
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- W2073876293 doi "https://doi.org/10.1021/jo011101y" @default.
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