A 1H and 13C nmr study of the radiation-induced degradation products of 2′-deoxythymidine derivatives: N-(2′-deoxy-β-D-erythropentofuranosyl) formamide

Abstract

N-(2′-Deoxy-β-D-erythropentofuranosyl) formamide is an ionizing radiation-induced degradation product of 2′-deoxythymidine. This work describes a facile chemical synthesis of this molecule, and discusses the results of an 1H and 13C nmr study. The rotational barrier to cis–trans isomerization about the amide linkage is calculated, and details of the molecular conformation of the cis and trans isomers in aqueous solution are presented.