Influence of the Solvent on the Stability of Aminopurine Tautomers and Properties of the Amino Group.

ABSTRACT: Amino derivatives of purine (2-, 6-, 8-, and N-NH₂) have found many applications in biochemistry. This paper presents the results of a systematic computational study of the substituent and solvent effects in these systems. The issues considered are the electron-donating properties of NH₂, its geometry, π-electron delocalization in purine rings and tautomeric stability. Calculations were performed in ten environments, with 1 < ε < 109, using the polarizable continuum model of solvation. Electron-donating properties were quantitatively described by cSAR (charge of the substituent active region) parameter and π-electron delocalization by using the HOMA (harmonic oscillator model of aromaticity) index. In aminopurines, NH₂ proximity interactions depend on its p

SUBMITTER: Jezuita A 

PROVIDER: S-EPMC10095612 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature