Furfural as a Marker of DNA Cleavage by Hydroxylation at the 5′ Carbon of Deoxyribose

Abstract

Depending upon the type of DNA substrate, a manganoporphyrin/KHSO5 system as artificial nuclease preferably attacks at the C1′ or C5′ atom of the deoxyribose moiety, whereby subsequent heating of the reaction mixtures leads to release of 5-methylene-2-furanone (5-MF) and furfural (FUR). The ratio 5-MF/FUR directly reflects the relative reactivities of the cleaving reagent with respect to C1′ and C5′. A possible reaction for the formation of FUR is outlined below. = terminal phosphate residue, B = nucleobase.