Chemical Modification of Guanine with Phenylglyoxyal

페닐글리옥살에 의한 구아닌의 화학적 변형

  • Park Inwon (Department of Chemistry, College of Liberal Arts and Sciences, Seoul National University) ;
  • Chang Sungkeun (Department of Chemistry, College of Liberal Arts and Sciences, Seoul National University) ;
  • Lee Kangryul (Department of Chemistry, College of Liberal Arts and Sciences, Seoul National University)
  • 박인원 (서울대학교 문리과대학 화학과) ;
  • 장성근 (서울대학교 문리과대학 화학과) ;
  • 이강렬 (서울대학교 문리과대학 화학과)
  • Published : 1972.10.30

Abstract

The adduct between phenylglyoxal and guanine was prepared. The structure of the adduct is similar to the glyoxal-guanine adduct. Aldehyde group of phenylglyoxal is added to 1-N of guanine base, and keto group is added to $N^2$ of guanine base. The structure of the adduct was determined by mass spectrometry, nuclear magnetic resonance spectroscopy and periodate oxidation. Periodate oxidation produced $N^2$-benzoyl-guanine from the adduct. On the basis of these results, ittvhas been assigned the structure I. The adduct is stable in alkaline solution: It does not dissociate into phenylglyoxal and guanine even after 2 hours heating at$60^{\circ}C$ at pH 12. The adduct is soluble in acidic ethanol, and is slightly soluble in neutral or alkaline water. It has a lower $A_{280}/A_{260}$ ratio at pH 1 compared to that of guanine.

Keywords

References

  1. Biochem. Biophys. Acta v.31 M. Staehelin
  2. Biochemistry v.6 M. Litt;V. Hancock
  3. Biochemistry v.8 M. Litt
  4. Progr. Nucleic Acid Res. & Mol. Biol. v.8 R. Shapiro;J.N. Davidson(ed.);W.E. Chon(ed.)
  5. Biochemistry v.8 R. Shapiro;B.I. Cohen;S.J. Shiney;H. Maurer
  6. The Korean Biochem. J. v.3 I. Park
  7. K.R. Lee;I. Park
  8. Biochim. Biophys. Acta v.72 B.G. Lane
  9. Anal. Biochem. v.30 S.M. Hecht;A.S. Gupta;N.J. Leonard
  10. Biochim. Biophys. Res. Comm. v.36 M.P. Schweizer
  11. Biochim. Biophys. Acta v.199 M.P. Schweizer
  12. Molekulyarnaya Biologia v.1 N.E. Broude;E.I.Budovskii;N.K.Kochetkov
  13. Biochemistry v.5 R. Shapiro;J. hachmann