Methylation of Phenyl Rings in Ester-Stabilized Phosphorus Ylides Vastly Enhances Their Protonophoric Activity

Chembiochem. 2024 Feb 14:e202300848. doi: 10.1002/cbic.202300848. Online ahead of print.ABSTRACTWe have recently discovered that ester-stabilized phosphorus ylides, resulting from deprotonation of a phosphonium salt such as [Ph3PCH2COOR]Br, can transfer protons across artificial and biological membranes. To create more effective cationic protonophores, we synthesized similar phosphonium salts with one ((heptyloxycarbonylmethyl)tri(p-tolyl)phosphonium bromide) or two ((butyloxycarbonylmethyl)tri(3,5-xylyl)phosphonium bromide) methyl substituents in the phenyl groups. The methylation enormously augmented both protonophoric activity of the ylides on planar bilayer lipid membrane (BLM) and uncoupling of mammalian mitochondria, which correlated with strongly accelerated flip-flop of their cationic precursors across the BLM.PMID:38353515 | DOI:10.1002/cbic.202300848

Source: Chembiochem - February 14, 2024 Category: Biochemistry Authors: Tatyana Rokitskaya Roman S Kirsanov Ljudmila S Khailova Alisa A Panteleeva Konstantin G Lyamzaev Galina A Korshunova Elena A Kotova Yuri N Antonenko Source Type: research