Interconversion of radical and nitrone forms of lysodektose--a new trisaccharide from Micrococcus lysodeikticus

Isolated from Micrococcus lysodeikticus, 6-O-(2-deoxy-2-(N-methyl)hydroxilamino-beta-D-glucopyranosyl)-alph a-alpha- trehalose (lysodektose) is oxidized by K3Fe(CN)6 in a stepwise manner to become a nitroxyl radical and a nitrone with a double bond in the fragment O-N = CH2 which could be reduced to the original hydroxylamine form with sodium borohydride. Thus derivatives of lysodektose specifically labelled with 2H and (or) 3H in the methyl group are easily obtained. When oxidized in cells poisoned with vitamin K analogues, lysodektose is transformed into nitrone concomitant with modification of its methyl group. Participation in the antioxidant defence of the bacteria is suggested for this new trisaccharide.