Identification of sugar degradation intermediates in a metalloporphyrin mediated DNA cleavage resulting from hydroxylation at C-5′

Abstract

Hydroxylation of poly(dA)·poly(dT) at the 5′ position of the deoxyribose units by the chemical nuclease Mn-TMPyP–KHSO₅[Mn–TMPyP = manganese(III) complex of meso-tetrakis(4-N-methylpyridiniumyl)porphyrin] followed by an additional thermal step provides 5′-aldehyde-3′,4′-unsaturated nucleosides which can be reduced by sodium borohydride and then hydrogenated with palladium on charcoal giving 2′,3′-dideoxyribonucleosides having the natural β or the non-natural α configuration at 4′.