Res. Chem. Intermed.
, Vol. 28, No. 2,3, pp. 175–190 (2002)
Also available online - www.vsppub.com
DEPMPO and lipophilic analogues: synthesis and EPR
, CLAUDINE FRÉJAVILLE and PAUL TORDO
Laboratoire SREP, UMR 6517, CNRS et Universités d’Aix-Marseille 1 et 3, Case 521,
Av. Esc. Normandie-Niemen, 13397 Marseille, cedex 20, France
Received 6 November 2001; accepted 20 November 2001
Abstract—DEPMPO (5-diethylphosphono-5-methyl-1-pyrroline N-oxide) is now recognised as a
major trap for the applications of spin-trapping techniques in biological milieu. We report herein
a new synthetic route for DEPMPO ending with the reductive cyclisation of the phosphorylated
° -nitroaldehyde 8. In comparison with the usual synthesis of DEPMPO, involving the oxidation
of the parent pyrrolidine 3, the new approach avoids the formation of over oxidation by-products thus
making easier the puri cation of DEPMPO. Lipophilic analogues of DEPMPO have been prepared
through addition of various Y
P(O)H on 2-methyl-1-pyrroline, followed by oxidation of the ensuing
pyrrolidines. These new nitrones were used to trap different radicals in water and organic solvents.
: DEPMPO; lipophilic analogues; spin-trapping; peroxyl radical; EPR simulations.
DTPA diethylenetriamide pentaacetic acid
SOD superoxide dismutase
XO xanthine oxidase
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