Serendipitous Synthesis of 5-Hydroxyuridine from 2',3'-O-isopropylidene N4-Acetylcytidine by Hypervalent Iodine(III)-Mediated Reaction - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue SYNLETT Année : 2023

Serendipitous Synthesis of 5-Hydroxyuridine from 2',3'-O-isopropylidene N4-Acetylcytidine by Hypervalent Iodine(III)-Mediated Reaction

Résumé

Whereas BAIB-TEMPO oxidation of 2’,3’-O-TBDMS-N4-acetylcytidine results in the expected 5'-carboxylic acid nucleoside, its 2',3'-O-isopropylidene analogue reacts in a radically different way. We have demonstrated here that hypervalent iodine(III) in water triggers an unprecedented oxidative cyclization leading to a mixture of C5-substituted O6,5'-cyclo-5,6-dihydro-uridines. This mixture of cyclouridines can be opened under basic conditions and, after deprotection, yields 5-hydroxyuridine, an important post-transcriptional modification of uridine at the wobble position (U34) of bacterial tRNA. NMR experimental values and calculations were performed to provide further insight on the specific reactivity of 2',3'-O-isopropylidene N4-acetylcytidine.
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hal-04235363 , version 1 (10-10-2023)

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Mary Anne Maverick, Mathieu Noël, Jean-Jacques Vasseur, Carine Baraguey, Françoise Debart, et al.. Serendipitous Synthesis of 5-Hydroxyuridine from 2',3'-O-isopropylidene N4-Acetylcytidine by Hypervalent Iodine(III)-Mediated Reaction. SYNLETT, 2023, ⟨10.1055/a-2174-2554⟩. ⟨hal-04235363⟩
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