1H and 13C NMR study of the interaction of formaldehyde on adenine and its derivatives

It has previously been shown that formaldehyde causes the formation of hydroxymethylated derivatives with nucleobases, but these were identified after separation of the reaction products; such handling might destroy labile derivatives or remove products present in small proportions. This work is based on a study of the reactivity of formaldehyde on adenine, adenosine and adenosine monophosphate in the reaction medium. It demonstrates the high reactivity of the N‐9 site of adenine, the reactivity of the hydroxymethyl at the C‐5′ of the ribose and brings to light such new derivatives as N‐9‐CH2OCH2OH and N‐6‐CH2OCH2OH. Further, the order of appearance of different derivatives and their approximate determination were achieved.