Synthesis of phosphodiester-type nicotinamide adenine dinucleotide analogs

Abstract

Fourteen phosphodiester-type β-nicotinamide adenine dinucleotide (NAD +) analogs were prepared starting from nicotinamide. The phosphodiester linkage was effectively assembled in 69–93% yields via condensation reaction between 2′,3′-di- O-acetyl nicotinamide mononucleotide and alcohols in the presence of 2,4,6-triisopropylbenzenesulfonyl chloride. The analog β-nicotinamide ribose-5-(2-phenylethyl) phosphate showed beneficial effects on cell growth of model microorganisms.