Solution structures of some ‘uridine dialdehyde’ derivatives

Abstract

When uridine is oxidised with periodate, the product is ‘uridine dialdehyde.’ Contrary to a previous report we have shown by ¹H n.m.r. spectroscopy that in solution, this compound is not polymeric but consists of a large number of isomers in dynamic equilibrium, although even at 400 MHz the spectrum is too complicated to analyse fully. However if the 5′-OH group is not present, such as in 5′-azido-5′-deoxyuridine dialdehyde or 5′-O-trityluridine dialdehyde, only three diastereoisomeric cyclic acetals are present. The ¹H n.m.r. spectrum at 400 MHz of the latter compound has been completely analysed and the identity and amounts of each of the three diastereoisomers have been determined.