New Coenzymically‐Active Soluble and Insoluble Macromolecular NAD + Derivatives

Abstract

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 ω‐carboxylic side chain. Carbodiimide coupling of the latter derivative to high‐molecular‐weight water‐soluble (polyethyleneimine, polylysine) and insoluble (aminohexyl‐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 %). Copyright © 1976, Wiley Blackwell. All rights reserved