B. Skalski, R. P. Steer, R. Verrall
Feb 1, 1991
Citations
0
Influential Citations
12
Citations
Journal
Journal of the American Chemical Society
Abstract
The photochemistry of N-[9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl) purin-6-yl] pyridinium chloride (1) has been investigated in aqueous solutions in the pH range 6-8 under aerobic and anaerobic conditions. A multistep mechanism of the photochemical transformation of 1 into the highly fluorescent nucleoside 2',3',5'-tri-O-acetylluminarosine (2) is proposed in which, as the first step, 1 undergoes light-induced, hydrolytic ring opening in the imidazole portion of the purine ring to form N-[5-formamido-6-[(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl) amino] pyrimidin-4-yl] pyridinium chloride (3)