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.

The 1-Carbamoyl-2-oxo-4,5-dihydroxyimidazolidine Component of ROS-Induced DNA Damage in White Blood Cells

“…In the case of the formamide modification, rotomers are present due to restricted rotation about the amide bond (15). The rotor states are unequally populated and are stable enough to yield distinct resonances in proton NMR spectra of nucleosides and oligomers containing this base modification (8, 16). Our measurements of the thymine glycol modification pertain to the cis stereoisomers.…”

A conformational study of the adducts of 2′-deoxythymidine and 2,2,6,6-tetramethyl-1,4-piperidone-N-oxyl by 1H and 13C nuclear magnetic resonance

“…I s to 15 s were collected; peak heights as a function of t served as input for a least-squares computer program (probable uncertainty -5%). The homonuclear 'H nOe experiments were carried out as described elsewhere (14). The nOe enhancements were expressed as the percentage change in peak height of the H6 (or Hl') resonances upon saturation of the HI ' (or H6) resonances.…”

Vicinal Lesions in X-irradiated DNA?

“…An example is the dinucleoside monophsophate d(GpT) X-irradiated in oxygenated solution. The cis and trans isomers are assigned in Figure 2 based on the work of Cadet et al . elution profile ( Figure 1) contains several produts of d(GpT) bearing familiar radiation-induced base modifications (Paul et al .…”