O-ADP-Ribosylation in the NAD/NADase system: 2-alkanols as efficient substrates

Several 2-alkanols (2-propanol, 2-butanol, 2-pentanol, etc.) were examined as substrates for ADP-ribosylation in the NAD/NADase enzymatic system. Even though these secondary alcohols have hydroxy groups that are subject to the steric influence of a methyl group, they were shown to be efficiently ADP-ribosylated. However, in the case of 3-alkanol (3-butanol), only slight ADP-ribosylation was observed. In this enzymatic reaction, 1,2-propanediol provided both 1-O- and 2-O-ADP-ribosylation products in the ratio 1:1 as determined by 1H-NMR spectrometry. On the other hand, an equimolar mixture system of 1- and 2-propanols provided major 1-O- and minor 2-O-ribosylation products in the ratio 4:1. This is the first report of O-ADP-ribosylation of terminal secondary alcohols with the NAD/NADase enzymatic system.