Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Theoretical Studies on the Photochemical Reaction of Psoralen. Photocycloaddition of Angelicin with Thymine

  • Ja Hong Kim (Department of Chemistry Education, Chonbuk National University) ;
  • Sung Ho Sohn (Department of Chemistry, Chonnam Nationall University) ;
  • Gae Soo Lee (Department of Chemistry, Chonnam Nationall University) ;
  • Kee Soo Yang (Department of Chemistry Education, Chonbuk National University) ;
  • Sung Wan Hong (Department of Chemistry, Woosuk University)
  • Published : 1993.08.20
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Abstract

A semiempirical methods (PM3-CI-UHF. etc.) for the evaluation of ground and excited state electronic structures of psoralens are applied to angelicin with thymine. The photocycloaddition reaction of angelicin with thymine were deduced to be formed by their preferable HSOMO-LUMO interactions. The photoadduct was inferred to be a C$_{4-}$cycloaddition product with the stereochemistry of cis-anti formed through [2+2] addition reaction between, the 3,4 double bonds of angelicin and the 5,6-double bond of thymine.

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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