Alkylation of Adenine, Adenosine, and NAD⁺with 1,3‐Propanesultone. Synthesis ofN⁶‐(3‐sulfonatopropyl)‐NAD⁺, a new NAD⁺derivative with substantial coenzyme activity

Abstract

Abstract The reactivity of 1,3‐propanesultone with adenine, adenosine, and NAD + was studied in order to prepare N 6 ‐(3‐sulfonatopropyl)‐NAD + ( 3b ), a new NAD + derivative substituted at the purine moiety with sunstantial coanzyme activity for several dehydrogenases. The regiochemistry of the alkylation at the purione nucleus was investigated by UV, 1 H‐NMR, and FAB‐MS proved to be a powerful tool for determining the molecular weight of these polar and poorly volatile compounds. In addition, regular framgmentation of 3b and other NAD + derivatives was observed.