Synlett 2017; 28(01): 73-77
DOI: 10.1055/s-0036-1588647
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© Georg Thieme Verlag Stuttgart · New York

5(4H)-Oxazolones as Effective Aminoacylation Reagents for the 3′-Terminus of RNA

Ziwei Liua, Cassandra Hansona, Ghinwa Ajrama, Laurent Boiteaua, Jean-Christophe Rossia, Grégoire Dangerb, Robert Pascal*a
  • aCNRS – University of Montpellier – ENSCM, Institut des Biomolécules Max Mousseron, UMR5247, CC17006, Pl. E. Bataillon, 34095 Montpellier Cedex 5, France   Email: robert.pascal@umontpellier.fr
  • bLaboratoire de Physique des Interactions Ioniques et Moléculaires, Aix-Marseille Université – CNRS, UMR 7345, Centre de Saint-Jérôme, Case 252, Avenue Escadrille Normandie-Niemen, 13397 Marseille, France
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Publication History

Received: 29 July 2016

Accepted after revision: 13 October 2016

Publication Date:
09 November 2016 (eFirst)

Abstract

Nucleosides and methylated nucleotide models were used as substrates to identify pathways for the chemical aminoacylation of ribonucleic acids (RNA) as a prerequisite for the evolution of translation. A selective and comparatively efficient reaction of a 5(4H)-oxazolone with the 2′- and 3′-OH of the ribonucleotide models was observed. Surprisingly, a similar reaction starting from an α-amino acid N-carboxyanhydride (NCA), selected as an acylating agent potentially leading to the unprotected ester required for translation, was not observed, which was confirmed using an acylated NCA equivalent. The reasons for this difference are analysed.

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