ENZYMATIC ALCOHOLYSES OF NAD - A NEW-TYPE OF ADP-RIBOSYLATION REACTION CATALYZED BY NAD GLYCOHYDROLASE

As part of studies concerning the transglycosidation action of NAD gly cohydrolase, the hydrolase-catalysed reaction of normal alkyl alcohols (six alcohols from methanol to 1-hexanol) has been investigated. All the alcoholic substrates were found to undergo ADP-ribosylation with v arying efficiencies, to give the corresponding O-ribosylated products (1-6). Yields (11-67%) were dependent upon the solubility of the subst rates in aqueous media and upon their inhibitory effect on the enzyme activity. H-1 NMR analyses demonstrated the alkyl beta-riboside struct ure of compounds 1-6 and the non-equivalence of the O-methylene proton s of their alkoxy groups. This is the first report of characterization of O-ribosylated products formed by the transglycosidation action of NAD glycohydrolase.