Determination of the syn-anti equilibrium of some purine 3':5'-nucleotides by nuclear-magnetic-relaxation perturbation in the presence of a lanthanide-ion probe

Eur J Biochem. 1977 Jun 15;76(2):601-5. doi: 10.1111/j.1432-1033.1977.tb11630.x.

Abstract

The aqueous solution conformation of four purine 3':5'-nucleotides varying in their substituents at C-6 and C-8 has been studied using gadolinium(III) to perturb the proton relaxation times. The ribose conformations are inferred. All the nucleotides are best described as being in a dynamic equilibrium between syn and anti conformations and the position of this equilibrium is not dramatically affected by changing the substituent at C-6. These nucleotides in their neutral base form slightly favour an anti conformation. In the presence of a bulky methylthio group at C-8 the equilibrium is shifted towards a dominance from the syn conformation due to steric repulsion factors.

MeSH terms

  • Binding Sites
  • Cyclic AMP
  • Cyclic IMP
  • Gadolinium*
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Nucleotides, Cyclic*

Substances

  • Nucleotides, Cyclic
  • Cyclic IMP
  • Gadolinium
  • Cyclic AMP