Methyltrioxorhenium (MTO) is a useful and selective catalyst for the oxidation of uracil and purine derivatives using environmentally friendly hydrogen peroxide (H2O2, 30\% water solution) or hydrogen peroxide/urea adduct (UHP) as oxygen atom donors. In particular, the MTO/UHP system constitutes a convenient combination to convert uracil derivatives into the biologically relevant 5,6-oxiranyl-5,6-dihydrouracils in good yields. Purine derivatives are selectively oxidized to the corresponding 1-oxides, the best yield being obtained in the presence of pyrazine-2-carboxylic acid (PCA). The oxidation of the plasmid pBG1 is also reported as the first example of double-strand DNA cleavage mediated by the catalytic system MTO/H2O2. (C)2000 Elsevier Science Ltd. All rights reserved.
Saladino, R., Carlucci, P., Danti, M., Crestini, C., Mincione, E. (2000). Selective oxidation of uracil and adenine derivatives by the catalytic system MeReO3/H2O2 and MeReO3/urea hydrogen peroxide. TETRAHEDRON, 56(51), 10031-10037 [10.1016/S0040-4020(00)00974-1].
Selective oxidation of uracil and adenine derivatives by the catalytic system MeReO3/H2O2 and MeReO3/urea hydrogen peroxide
CRESTINI, CLAUDIA;
2000-01-01
Abstract
Methyltrioxorhenium (MTO) is a useful and selective catalyst for the oxidation of uracil and purine derivatives using environmentally friendly hydrogen peroxide (H2O2, 30\% water solution) or hydrogen peroxide/urea adduct (UHP) as oxygen atom donors. In particular, the MTO/UHP system constitutes a convenient combination to convert uracil derivatives into the biologically relevant 5,6-oxiranyl-5,6-dihydrouracils in good yields. Purine derivatives are selectively oxidized to the corresponding 1-oxides, the best yield being obtained in the presence of pyrazine-2-carboxylic acid (PCA). The oxidation of the plasmid pBG1 is also reported as the first example of double-strand DNA cleavage mediated by the catalytic system MTO/H2O2. (C)2000 Elsevier Science Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
