Regioselectivity and mechanism of transpurination reactions in the guanine nucleosides series
Abstract
The transpurination reaction of the fully acetylated
derivatives of guanosine and its
7-β-D-ribofuranosyl regioisomer with
2-acetoxyethyl acetoxymethyl ether has been studied using high
performance liquid chromatography (HPLC). The regioselectivity
of glycosyl exchange observed in the early stages of the reaction
suggests that the unsubstituted nitrogen atoms of the imidazole
portion (N7 and N9) are, exclusively, sites of direct
glycosylation in the case of guanine derivatives. The results
lead to the conclusion that the mechanism of the glycosylation
reaction of guanine is different to that of adenine.
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