Formation of highly fluorescent adducts between 2'-deoxyguanosine and amino acids by ionizing radiation

Hiroaki Terato, Miyuki Yoshimura, Masae Hayashi, Yoshihiko Ohyama, Osamu Yamamoto, Hiroshi Ide

Research output: Contribution to journalArticle

Abstract

Gamma-irradiation of aqueous solutions containing DNA and alcohols is known to generate fluorescent products. In this study, aqueous solutions containing 2'-deoxyguanosine (dG) and amino acids with an aliphatic hydroxyl group [serine (Ser) or threonine (Thr)] were irradiated and analyzed for fluorescence. Both irradiated solutions showed a similar fluorescence profile with the excitation maximum ~310nm and the emission maximum ~370nm. The fluorescence profiles were very close to that of 2-aminopurine, known as a highly fluorescent base. In the irradiation of dG with Ser, two distinct fluorescent products were observed in liquid chromatographic analysis. The major product was further purified by chromatography. Mass spectrometry (MS) showed that the major fluorescent product was a dG adduct bearing a Ser fragment at the C-6 position. In the case of dG with Thr, only one major fluorescent product was observed. The purified product seemed to be a C-6 adduct of dG with a Thr fragment based on MS and NMR analyses. These structural data for the fluorescent products suggest that C-6 adduct formation of dG was the key to generating fluorescence. This is consistent with our previous finding that the adduct between dG and tert-butanol at C-6 is highly fluorescent. Copyright (C) 1998 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)183-191
Number of pages9
JournalAnalytica Chimica Acta
Volume365
Issue number1-3
DOIs
Publication statusPublished - Jun 5 1998
Externally publishedYes

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Deoxyguanosine
Ionizing radiation
Ionizing Radiation
amino acid
Amino Acids
fluorescence
Threonine
Fluorescence
Serine
Mass spectrometry
Mass Spectrometry
irradiation
Bearings (structural)
aqueous solution
mass spectrometry
2-Aminopurine
tert-Butyl Alcohol
Irradiation
Liquid chromatography
Chromatography

Keywords

  • 2'-Deoxyguanosine
  • Amino acids
  • Fluorescence
  • Radiation product

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Environmental Chemistry
  • Spectroscopy

Cite this

Formation of highly fluorescent adducts between 2'-deoxyguanosine and amino acids by ionizing radiation. / Terato, Hiroaki; Yoshimura, Miyuki; Hayashi, Masae; Ohyama, Yoshihiko; Yamamoto, Osamu; Ide, Hiroshi.

In: Analytica Chimica Acta, Vol. 365, No. 1-3, 05.06.1998, p. 183-191.

Research output: Contribution to journalArticle

Terato, Hiroaki ; Yoshimura, Miyuki ; Hayashi, Masae ; Ohyama, Yoshihiko ; Yamamoto, Osamu ; Ide, Hiroshi. / Formation of highly fluorescent adducts between 2'-deoxyguanosine and amino acids by ionizing radiation. In: Analytica Chimica Acta. 1998 ; Vol. 365, No. 1-3. pp. 183-191.
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