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THE THYMIDINE‐PSORALEN PHOTOADDITION. A MODEL APPROACH
Author(s) -
Décout JeanLuc,
Lekchiri Yahya,
Lhomme Jean
Publication year - 1992
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1992.tb08505.x
Subject(s) - psoralen , thymidine , thymine , adduct , chemistry , diastereomer , derivative (finance) , intramolecular force , stereochemistry , photochemistry , methoxsalen , dna , organic chemistry , biochemistry , biology , financial economics , economics , immunology , psoriasis
— In order to investigate the photoreactions between the thymidine and the psoralen chromophores and to devise a synthetic route to prepare thymidine‐5‐methoxypsoralen adducts, we have prepared and studied a compound in which thymidine is linked to a 5‐methoxypsoralen derivative by a diester chain. Irradiation at 365 nm carried out at usual concentrations (10– 3 M ) leads exclusively to one diastereoisomer of an intramolecular 3,4 cis‐anti [2+2] adduct. No photodimerization is observed in these conditions. These results are compared to those obtained for models studied previously in which the thymine and the psoralen rings are linked by polymethylenic chains of varying length.