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

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Abstract
The chemical reduction of model compounds 1-(2'',6''-dichlorobenzyl)-3-halogenopyridinium to the corresponding 1,4-dihydropyridines is proved by spectroscopic analysis. 3-Iodopyridine-adenine dinucleotide was prepared by enzymic transglycosidation. 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 active as H acceptors with alcohol as a substrate. The absorption band at 290 nm of cinnamaldehyde was a very sensitive tool for studying the enzymic reaction. With yeast alcohol dehydrogenase [EC 1.1.1.1], only slight activity was detected. 3-Halogenopyridine-adenine dinucleotides are competitive inhibitors of yeast alcohol dehydrogenase [pig heart, dogfish], lactate dehydrogenase [EC 1.1.1.27] and malate dehydrogenase [EC 1.1.1.37]. 3-Iodopyridine-adenine dinucleotide as a heavy-atom derivative for X-ray structure determination is proposed.