The triplex forming ability of nonnatural nucleobases

A computational approach

R. Fenyö, Z. Tímár, I. Pálinkó, B. Penke

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Nucleotide bases with the capability of specific H-bonding interactions with base pairs in the major groove of DNA have been designed. During the procedure several factors were taken into account: the molecule (i) should contain substructure capable of Hoogsteen H-bonding with the purine base of the Watson-Crick doublet; (ii) should be cyclic and planar; (iii) for practical purposes it should be chemically stable; and (iv) the triplet should also be stable. Calculations by semiempirical methods lead to four compounds as possible triplet forming nucleobases: quinolin-2-ylamine, indol- 2-ylamine, pyridin-2-ylamine and 2-aminopyrrol. They all meet the above criteria. Geometry optimization of the triplets resulted in H-bond distances as well as H-bond energies. (C) 2000 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)101-105
Number of pages5
JournalJournal of Molecular Structure: THEOCHEM
Volume496
DOIs
Publication statusPublished - Jan 7 2000

Fingerprint

purines
quinoline
nucleotides
Nucleotides
substructures
Base Pairing
grooves
DNA
deoxyribonucleic acid
Molecules
optimization
Geometry
geometry
molecules
interactions
energy
purine

Keywords

  • Geometric data
  • H-bond energies
  • Semiempirical methods
  • Triplet forming nucleobases

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

Cite this

The triplex forming ability of nonnatural nucleobases : A computational approach. / Fenyö, R.; Tímár, Z.; Pálinkó, I.; Penke, B.

In: Journal of Molecular Structure: THEOCHEM, Vol. 496, 07.01.2000, p. 101-105.

Research output: Contribution to journalArticle

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