The structures of adducts from the reaction between guanosine and glycidaldehyde (oxiranecarbaldehyde): a 15N labelling study

Abstract

Reaction of guanonsine (1a) with racemic glycidaldehyde (2) in aqueous medium at pH 10 gives 5,9-dihydro-9-oxo-3-β-D-ribofuranosylimidazo[1,2-a]purine (1,N²-ethenoguanosine)(3c), its 7-hydroxymethyl derivative (3a), and methylene-7,7′-bis-5,9-dihydro-9-oxo-3-β-D-ribofuranosylimidazo[1,2-a]purine (5); the structures of adducts (3a) and (5) were deduced from ¹³C n.m.r. analysis of ¹⁵N labelled adducts derived from [1-¹⁵N]guanosine (1b) and [¹⁵NH₂]guanosine (1c).