New coenzymically-active soluble and insoluble macromolecular NAD+ derivatives.
Reaction in dimethyl sulfoxide of nicotinamide 8-bromoadenine dinucleotide with the disodium salt of 3-mercaptopropionic acid afforded nicotinamide-8-(2-carboxyethylthio)adenine dinucleotide, a new NAD+ analogue functionalized at the adenine C-8 position by an omega-carboxylic side chain. Carbodimide coupling of the latter derivative to high-molecular-weight water-soluble (polyethyleneimine, polylysine) and insoluble (aminohexy)-Sepharose) polymers gave the corresponding macromolecular NAD+ analogues. These derivatives have been shown to be enzymically reducible. The polyethyleneimine analogue showed a substantial degree of efficiency relative to free NAD+ with yeast alcohol dehydrogenase (47%) but a considerably lower one with rabbit muscle lactate dehydrogenase (3%); the polylysine analogue showed a low degree of efficiency with both enzymes (5-6%).
D000429:Alcohol Oxidoreductases / Q000378:metabolism; D007770:L-Lactate Dehydrogenase / Q000378:metabolism; D009132:Muscles / Q000201:enzymology; D009243:NAD / Q000031:analogs & derivatives* / Q000494:pharmacology; D011422:Propionates; D012441:Saccharomyces cerevisiae / Q000201:enzymology; D012995:Solubility; D013053:Spectrophotometry; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship; D013438:Sulfhydryl Compounds
D011422:Propionates; D013438:Sulfhydryl Compounds; D009243:NAD; D000429:Alcohol Oxidoreductases; D007770:L-Lactate Dehydrogenase