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Enzymatic alcoholyses of NAD: A New type of ADP‐ribosylation reaction catalysed by NAD glycohydrolase
Author(s) -
Tonooka Shuichi,
Azuma Ichiro
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970905
Subject(s) - chemistry , nad+ kinase , stereochemistry , enzyme , alkyl , alkoxy group , methylene , medicinal chemistry , organic chemistry
As part of studies concerning the transglycosidation action of NAD glycohydrolase, 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 varying efficiences, to give the corresponding O ‐ribosylated products ( 1–6 ). Yields (11–67%) were dependent upon the solubility of the substrates in aqueous media and upon their inhibitory effect on the enzyme activity. 1 H NMR analyses demonstrated the alkyl β‐riboside structure of compounds 1–6 and the non‐equivalence of the O ‐methylene protons of their alkoxy groups. This is the first report of characterization of O ‐ribosylated products formed by the transglycosidation action of NAD glycohydrolase.