Evaluation of the hydrogen bond energy of base pairs formed between substituted 9-methyladenine derivatives and 1-methyluracil by use of molecular orbital theory

Nucleic Acids Symp Ser. 2000:(44):237-8. doi: 10.1093/nass/44.1.237.

Abstract

Systematic substituent effects on the stability of the hydrogen bonding between substituted 9-methyladenine derivatives (Ax) and 1-methyluracil (U) were studied by ab initio molecular orbital theory. Predicted substituent effects on the hydrogen bond energies of Ax-U base pairs were in good agreement with those observed for experimental binding constants. Ab initio calculation is effective for evaluation of the stability of the hydrogen-bonding pairs of chemically modified nucleic acid base analogues. In contrast to the substitution effect of uracil on hydrogen bond energies of A-Ux base pairs, it is difficult to systematically interpret the substitution effect of adenine derivatives for Ax-U base pairs.

MeSH terms

  • Adenine / analogs & derivatives*
  • Adenine / chemistry*
  • Base Pairing
  • Drug Design
  • Drug Stability
  • Hydrogen Bonding
  • Models, Chemical
  • Molecular Structure
  • RNA / chemistry*
  • Thermodynamics
  • Uracil / analogs & derivatives*
  • Uracil / chemistry*

Substances

  • Uracil
  • 1-methyluracil
  • RNA
  • 9-methyladenine
  • Adenine