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STRUCTURE OF 3‐CARBETHOXYPSORALEN PHOTOLYSIS PRODUCTS
Author(s) -
Moysan A.,
Cazaussus A.,
Gaboriau F.,
Blais J. C.,
Sellier N.,
Vlgny P.
Publication year - 1988
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.1751-1097.1988.tb02734.x
Subject(s) - chemistry , photodissociation , double bond , molecule , photochemistry , furan , cyclobutane , mass spectrometry , solvent , pyrone , fluorescence , bond cleavage , psoralen , ring (chemistry) , organic chemistry , chromatography , dna , catalysis , biochemistry , physics , quantum mechanics
— Upon UV‐A irradiation(320–400 nm), the photorcaction of psoralens either with a solvent molecule or with a second psoralen molecule competes with the well‐known photoaddition of psoralens to DNA. In the present study, a structural assignment of the 3‐carbethoxypsoralen (3‐CPs) photolysis products is proposed on the basis of their chromatographic (high performance liquid chromatography) and of their spectroscopic (absorption, fluorescence, mass spectrometry and 1 H Nuclear Magnetic Resonance) properties. Four photolysis products have been isolated and identified. The first one results from a water molecule addition on the 4′,5′ double bond of 3‐CPs, the second from an ethanol molecule addition on the 4′,5′ double bond. Two cyclobutane type dimers of 3‐CPs have also been characterized. These results confirm that, in protic solvents, the furan(4′,5′) double bond of 3‐CPs is more photoreactive than the pyrone(3,4) double bond.