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

Synlett DOI: 10.1055/a-2174-2554 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-dihydrouridines. 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. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synlett - October 18, 2023 Category: Chemistry Authors: Maverick, Mary Anne No ël, Mathieu Vasseur, Jean-Jacques Baraguey, Carine Debart, Fran çoise Smietana, Michael Tags: cluster Source Type: research