Photochemical reactions of 5-fluorouracil and 5-fluoro-2′-deoxyuridine with Nα-acetyl-L-tryptophan N-ethylamide in aqueous solution

Add time:08/24/2019    Source:sciencedirect.com

Irradiation of 5-fluorouracil (1) and 5-fluoro-2′-deoxyuridine (2) with Nα-acetyl-L-tryptophan N-ethylamide (5) in aqueous buffered (pH 7) solutions led to Nα-acetyl-2-(uracil-5-yl) tryptophan N-ethylamide (6) and Nα-acetyl-2-[l-(2-deoxy-β-l) erythro-pentofuranosyl)uracil-5-yl] tryptophan N-ethylamide (7), respectively, as the main photoproducts. In addition, compounds 6 and 7 were synthesized by photochemical coupling of 5-bromouracil (3) and 5-bromo-2′-deoxyuridine (4), respectively, with 5. The formation of cross-links between 5-fluorouracil-substituted nucleic acids and tryptophan-containing proteins can be detected by fluorescence characteristic of the uracil-tryptophan fluorophore. The mechanism proposed for the formation of photoproducts 6 and 7 involves electrophilic attack of the 5-uracilyl cation on the indole ring of 5.

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