Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Theoretical Studies on the Photochemical Reaction of Psoralen with Purine and Pyrimidine Base

  • Kim Ja Hong (Department of Chemistry Education, Chonbuk National University) ;
  • Sohn Sung Ho (Department of Chemistry Education, Chonbuk National University)
  • Published : 1992.04.20
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Abstract

The spectroscopic studies of the 5,7-dimethoxycoumarin(5,7-DMC) and 4,5',8-trimethylpsoralen(TMP) and the conformational stability of 5,7-DMC-thymidine, 4,5',8-TMP-thymine were carried out by the CNDO/S and molecular mechanics calculation. Theoretical transition energies and direction of polarizations calculated by the CNDO/S method have been used for the interpretation of the observed results. The calculated absorption spectra of 5,7-DMC are qualitatively similar to experimental ones with their characteristic visible bands. MM2 force field calculation on the possible $C_4-cyclophotoadducts$ formed between 5,7-DMC and thymidine through a cycloaddition. of $C_3$, $C_4$ bond of 5,6-DMC to $C_5$, $C_6$ bond of thymidine showed the most stable photocycloadduct to have the anti-head to tail configuration. The major photoadduct of 4,5',8-TMP-thymine has the cis-anti configuration.

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  1. Photoreactivity of Furocoumarins and DNA in PUVA Therapy: Formation of Psoralen−Thymine Adducts vol.112, pp.44, 2008, https://doi.org/10.1021/jp805523d