Preparation and Properties of 3‐Halopyridine–adenine Dinucleotides, NAD + Analogues and of Model Compounds

Abstract

The preparation of model compounds 1‐(2′,6′‐dichlorobenzyl)‐3‐halogenopyridinium and the study of their properties were achieved. Their chemical reduction to the corresponding 1,4‐dihydro‐pyridines is proved by spectroscopic analysis. 3‐lodopyridine‐adenine dinucleotide was prepared by enzyme transglycosidation while the 3‐chloro, 3‐bromo and 3‐iodo pyridine‐adenine dinucleotides were synthesized from 3‐amino‐pyridine‐adenine dinucleotide. The 3‐halogenopyridine‐adenine dinucleotides were proved to be active as hydrogen acceptors with alcohol as a substrate. The absorption band at 290 nm of cinnamaldehyde appeared to be a very sensitive tool for studying the enzyme reaction. With the alcohol dehydrogenase from yeast, only slight activity was detected. 3‐Halogenopyridine‐adenine dinucleotides are competitive inhibitors with respect to nicotinamide‐adenine dinucleotide with alcohol dehydrogenase from yeast, lactate dehydrogenase and malate dehydrogenase. The use of 3‐iodopyridine‐adenine dinucleotide as a heavy‐atom derivative for X‐ray structure determination is proposed. Copyright © 1976, Wiley Blackwell. All rights reserved