Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Theoretical Studies on the Photocycloaddition Reaction of Psoralen with Thymidine

  • Kim, Ja-Hong (Department of Chemistry Education, Chonbuk National University) ;
  • Oh, Se-Woung (Department of Chemistry, MokPo College) ;
  • Lee, Yoon-Sup (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Shim, Sang-Chul (Department of Chemistry, Korea Advanced Institute of Science and Technology)
  • Published : 1987.08.20
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Abstract

The theoretical studies on the photocycloaddition reaction of 5,7-dimethoxycoumarin and 4',5'-dihydropsoralen with thymidine were carried out as a model for photosensitizing reaction of psoralen with DNA. The results are in reasonable agreement with experimental observations. The photoadducts between dimethoxycoumarin and thymidine were predicted to be $C_{4}$-cycloadducts through the cycloaddition of 3,4-pyrone double bond of dimethoxycoumarin to 5,6 double bond of thymidine. The major photoadduct of 4',5'-dihydropsoralen with thymidine has the anti head-to-head stereochemistry.

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  1. The family of furocoumarins: Looking for the best photosensitizer for phototherapy vol.199, pp.1, 1987, https://doi.org/10.1016/j.jphotochem.2008.04.013
  2. Photoreactivity of Furocoumarins and DNA in PUVA Therapy: Formation of Psoralen−Thymine Adducts vol.112, pp.44, 2008, https://doi.org/10.1021/jp805523d