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Methyl Linoleate Oxidation via Electron Transfer in Competition with $^1O_2$ Formation Photosensitized N-Acetyl-L-Tryptophan 3-Methyl Indole

  • Yoon, Min-Joong (Department of Chemistry, College of Science, Chungnam National University) ;
  • Song, Moon-Young (Department of Chemistry, College of Science, Chungnam National University) ;
  • Cho, Dae-Won (Department of Chemistry, College of Science, Chungnam National University)
  • Published : 1985.10.20

Abstract

The efficiency of photosensitization of methyl linoleate (ML) oxidation by N-acetyl-L-trypophan(NAT) and 3-methyl indole(scatole) was markedly enhanced by increased concentration of ML in ethanol solution. The fluorescence intensities of sensitizers were observed to be quenched by ML, indicating that ML interacts with the indole excited singlet state. The inhibition of photosensitization by azide demonstrated a possible role of singlet oxygen in the photosensitization. The steady state kinetic treatment of azide inhibition of photosensitization was expected to show linear increase of reciprocal yield of ML oxidation product vs. reciprocal ML concentration at constant azide concentration, but the actual slope was nonlinear. This indicates another competing reaction involved in the photosensitization, As a possible competing reaction, electron transfer from ML to the excited sensitizer was proposed, since the measured fluorescence quenching rate constant closely resembled electron transfer rate constant determined from ML concentration dependence of oxidation product formation.

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References

  1. Science v.179 A.A. Lamola;T. Yamane;A.M. Trozzolo
  2. J. Phys. Chem. v.74 E.P. Kirby;R.F. steiner
  3. J. Am. Chem. Soc. v.100 K.A. Brown-Wensley;S.L. Mattes;S. Farid
  4. Principles of Fluorescence Spectroscopy J.R. Lakowicz
  5. J. Phys. Chem. v.75 C.R. Goldschmidt;R. Potashnik;M. Ottlolenhi
  6. Chem. Phys. Lett. v.10 G.N. Taylor
  7. Advances in Chemistry Singlet Oxygen C.S. Foote
  8. J. Am. Chem. Soc. v.102 J. Eriksen;C.S. Foote
  9. Biochim. Biophys. Acta v.559 H.U. Weltzine
  10. J. Invest. Dermatol. v.74 I.E. Kochevar
  11. Photochem. Photobiol. v.37 I.E. Kochevar;M. Yoon
  12. Photochem. Photobiol. v.19 P. Walrant;R. Santus
  13. Photochem. Photobiol. v.20 P. Walrant;R. Santus
  14. Agric. Biol. Chem. v.41 R. Yamauchi;S. Matsushida
  15. Photochem. Photobiol. v.29 E. Amouyal;A. Bernas;D. Grand
  16. Mol. Photochem. v.1 F.G.r. Moses;R.S.H. Liu;B.M. Muroe