Photoreaction of 5-methoxypsoralen with thymidine. Isolation and characterization of a pyrone-side monoadduct involving the pyrimidine methyl group

Anselmino, Catherine; Cadet, Jean

doi:10.1016/1011-1344(94)07072-v

Cited by 5 publications

(3 citation statements)

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“…Irradiation of a 10:1 mixture of thymidine and 5-MOP in the dry state led to the formation of five photoadducts which were efficiently separated by HPLC on an ODS Ultrasphere column (Figure 1) and identified as the two pairs of cis-syn and cis-anti diastereoisomers of 5-MOP pyrone-side monocycloadduct (vide infra). It should be noted that the slowest HPLC eluting photoadduct was assigned as a 5-MOP-thymidine photoadduct involving the covalent binding of 3,4-dihydro-5-methoxypsoralen-3-yl radical to -thymidinyl radical (29).…”

Section: Resultsmentioning

confidence: 99%

Characterization of the cis-syn and cis-anti diastereoisomers of 5-methoxypsoralen pyrone-side monocycloadducts to thymidine

Anselmino

Voituriez²,

Cadet³

1993

Chem. Res. Toxicol.

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The photoreaction of 5-methoxypsoralen (5-MOP) with thymidine as a DNA model compound was investigated under dry-state conditions. In this respect, a thin film of thymidine and 5-MOP in a ratio 10:1 was exposed to 350-nm UV light. Four [2 + 2] photocycloadducts were isolated in a 0.5-2.2% yield with respect to 5-MOP by HPLC and characterized as two pairs of cis-syn and cis-anti diastereoisomers, respectively, on the basis of extensive spectroscopic measurements, including UV, fast atom bombardment mass spectrometry, 1H and 13C NMR, and CD. Information concerning the absolute configuration of the four photocycloadducts was inferred from detailed nuclear Overhauser enhancement experiments. This is indicative of a 3R,4S,5R,6S and a 3S,4R,5S,6R configuration for the cis-anti cycloadducts and a 3S,4R,5R,6S) and a 3R,4S,5S,6R configuration for the cis-syn cycloadducts. In addition, conformational features of the four photocycloadducts were obtained from consideration of various 1H NMR measurements including NOE data.

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Section: Resultsmentioning

confidence: 99%

Characterization of the cis-syn and cis-anti diastereoisomers of 5-methoxypsoralen pyrone-side monocycloadducts to thymidine

Anselmino

Voituriez²,

Cadet³

1993

Chem. Res. Toxicol.

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“…Only, the formation of cis-syn furan-thymidine monoadducts has been evidenced recently (8). The photoreactions of 5-MOP with thymidine in the dry state have been investigated (8,18,19). In these conditions, cis-syn and -anti pyrone and cis-syn furan adducts could be isolated and characterized (8,181.…”

Section: Discussionmentioning

confidence: 99%

“…Most of these experiments are conducted in the solid state in the presence of a large excess of base to enable the psoralen-base photoaddition to take place and to compete with the highly favored psoralen photodimerization (9.10). Even operating under such conditions, mixtures of psoralen-base monoadducts are obtained in very low yields (8, [11][12][13][14][15][16][17][18][19].…”

Section: Introductionmentioning

confidence: 99%

Thymidine‐Psoralen Photoaddition: Stereoselective Formation of A trans‐syn Pyrone Adduct

Décout

Guendouz

Lhomme

1996

Photochem & Photobiology

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To study the photoreactions between thymidine and psoralen and to devise a synthetic route to prepare thymidine-5-methoxypsoralen adducts, we have synthesized a compound in which thymidine is linked to a 5-methoxypsoralen derivative by a short flexible chain located to allow only the formation of syn intramolecular [2+2] cycloadducts. Irradiation at 365 nm carried out at usual concentrations (10-2-10-3 M ) resulted in a regioselective dimerization involving the 3,4 double bonds. Extreme dilution (c I 5 x M ) was necessary to observe the intramolecular photoaddition, which produces exclusively the 3,4-trans-syn adduct. These results are compared to those obtained previously with similar heterodimers that lead exclusively to the 3,4-cis-anti thymine or thymidine-psoralen adduct on exposure to near UV light.

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Chapter 6.2 Six-membered ring systems: Diazines and benzo derivatives

Groziak

1996

Progress in Heterocyclic Chemistry

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Photoreaction of 5-methoxypsoralen with thymidine. Isolation and characterization of a pyrone-side monoadduct involving the pyrimidine methyl group

Cited by 5 publications

References 28 publications

Characterization of the cis-syn and cis-anti diastereoisomers of 5-methoxypsoralen pyrone-side monocycloadducts to thymidine

Characterization of the cis-syn and cis-anti diastereoisomers of 5-methoxypsoralen pyrone-side monocycloadducts to thymidine

Thymidine‐Psoralen Photoaddition: Stereoselective Formation of A trans‐syn Pyrone Adduct

Chapter 6.2 Six-membered ring systems: Diazines and benzo derivatives

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