4-aminobenzimidazole-1-methylthymine: A model for investigating hoogsteen base-pairing between adenine and thymine

Yevgeniy Nosenko, Maksim Kunitski, Tina Stark, Michael Göbel, Tarakeshwar Pilarisetty, Bernhard Brutschy

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

We report the infrared spectrum of the 4-aminobenzimidazole-1-methylthymine (4ABI:1MT) heterodimer, detected by femtosecond multiphoton ionization. Based on calculations of both the harmonic and the anharmonic frequencies, the observed vibrational spectrum is assigned to a structure that mimics the Hoogsteen base pairing of adenine and thymine. A notable observation made in the course of this study is that there is a significant imbalance in the observed strengths of the H-bonds. While the N•••H-N bond reveals a large red shift of >700 cm -1 for the NH stretch frequency, the N-H•••O bond is characterized by only a 50 cm -1 shift. The importance of this observation in the formation of Hoogsteen duplexes by thymine-based oligonucleotides is discussed.

Original languageEnglish (US)
Pages (from-to)11403-11411
Number of pages9
JournalJournal of Physical Chemistry A
Volume115
Issue number41
DOIs
StatePublished - Oct 20 2011

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Thymine
thymine
adenines
Adenine
oligonucleotides
Vibrational spectra
Oligonucleotides
red shift
vibrational spectra
Ionization
infrared spectra
Infrared radiation
harmonics
ionization
shift
4-aminobenzimidazole-1-methylthymine

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

4-aminobenzimidazole-1-methylthymine : A model for investigating hoogsteen base-pairing between adenine and thymine. / Nosenko, Yevgeniy; Kunitski, Maksim; Stark, Tina; Göbel, Michael; Pilarisetty, Tarakeshwar; Brutschy, Bernhard.

In: Journal of Physical Chemistry A, Vol. 115, No. 41, 20.10.2011, p. 11403-11411.

Research output: Contribution to journalArticle

Nosenko, Yevgeniy ; Kunitski, Maksim ; Stark, Tina ; Göbel, Michael ; Pilarisetty, Tarakeshwar ; Brutschy, Bernhard. / 4-aminobenzimidazole-1-methylthymine : A model for investigating hoogsteen base-pairing between adenine and thymine. In: Journal of Physical Chemistry A. 2011 ; Vol. 115, No. 41. pp. 11403-11411.
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