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- W2049370910 abstract "The first total chemical synthesis of a cis-syn furan-side photoproduct between a psoralen derivative and thymidine is described. The key step in the synthesis was an intramolecular [2 + 2] photocycloaddition, which directed the stereochemical course of the reaction to afford a product equivalent to that formed when a psoralen molecule is allowed to react at a 5‘-TpA-3‘ site in DNA. A model system consisting of a simple benzofuranyl acid tethered to the 5‘ hydroxyl of thymidine showed that it was possible to bias the stereochemical outcome of the photochemical reaction in favor of the desired cis-syn product. Further refinement of the model system allowed for the elaboration of a benzofuran−thymidine photoproduct into a cis-syn 2-carbomethoxypsoralen furan-side thymidine monoadduct. The stereochemistry of all photoproducts as established by NMR and CD spectroscopy indicated that the cycloadditions occurred on the 3‘ face of thymine, the equivalent of a psoralen monoadduct in a 5‘-TpA-3‘ site in DNA. Previously, the inability to program the sequence context of psoralen−DNA adducts has constrained certain biological studies, such as experiments aimed at deciphering the transcriptional effects of adducts at TATA sites. This method is a key step toward overcoming that problem." @default.
- W2049370910 created "2016-06-24" @default.
- W2049370910 creator A5009785229 @default.
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- W2049370910 date "1996-01-01" @default.
- W2049370910 modified "2023-10-03" @default.
- W2049370910 title "Total Synthesis of a <i>Cis</i>-Syn 2-Carbomethoxypsoralen Furan-Side Thymidine Monoadduct" @default.
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- W2049370910 doi "https://doi.org/10.1021/ja960511e" @default.
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