Chemical Research Letters, May 2021. The appropriate choice of redox mediator can avoid electrode passivation and overpotential, which strongly inhibit the efficient activation of substrates in electrolysis. Safety of Tributyl(thiophen-2-yl)stannane,54663-78-4, Name is Tributyl(thiophen-2-yl)stannane, SMILES is CCCC[Sn](CCCC)(CCCC)C1=CC=CS1, belongs to pyrrolines compound. In a document, author is Xu, GZ, introduce the new discover.
Cross-linking of proteins by 3-(trifluoromethyl)-2,5-hexanedione. Model studies implicate an unexpected amine-dependent defluorinative substitution pathway competing with pyrrole formation
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-(l-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.
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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem