Synthesis of a New Spin Trap: 2-(Diethoxyphosphoryl)-2-phenyl-3,4-dihydro-2H-pyrrole 1-Oxide.
Recently, the synthesis of a new phosphorylated nitrone, 2-(diethoxyphosphoryl)-2-methyl-3,4-dihydro-2H-pyrrole 1-oxide (DEPMPO) (2) was described. The presence of the phosphorylated group strongly stabilized the DEPMPO-superoxide spin adduct. To understand the role of the diethoxyphosphoryl group in this stabilization, a new phosphorylated nitrone, 2-(diethoxyphosphoryl)-2-phenyl-3,4-dihydro-2H-pyrrole 1-oxide (DEPPPO) (7), was prepared through a four-step synthetic pathway, and its ability to trap free radicals was investigated. Data obtained from spin trapping experiments of a wide variety of free radicals generated in situ showed the formation of two diastereoisomers spin adducts with different phosphorus and hydrogen coupling constants. Superoxide trapping by DEPPPO gave a persistent nitroxide spin adduct, and its half-time life was measured and compared to that of the DEPMPO analogue.
Karoui
Hakim
H
Laboratoire Structure et Réactivité des Espèces Paramagnétiques, case 521, CNRS UMR 6517 "Chimie, Biologie et Radicaux Libres", Universités d'Aix-Marseille I et III, Centre de Saint Jérôme, Av. Escadrille Normandie Niemen, 13397 Marseille Cedex 20, France.
Nsanzumuhire
Céline
C
Le Moigne
François
F
Tordo
Paul
P