Synthesis of tRNA analogues containing a terminal ribose locked in the South conformation to study tRNA-dependent enzymes. Issue 11 (27th February 2018)

• Record Type: Journal Article
• Authors: Iannazzo, Laura; Fonvielle, Matthieu; Braud, Emmanuelle; Hřebabecký, Hubert; Procházková, Eliška; Nencka, Radim; Mathé, Christophe; Arthur, Michel; Etheve-Quelquejeu, Mélanie
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 11(2018)
• Page Start: 1903
• Page End: 1911
• Publication Date: 2018-02-27
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob00019k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Synthesis and biological evaluation of tRNA analogues containing a terminal ribose locked in the South conformation. Abstract : We report here the synthetic route of two constrained dinucleotides and the determination of the sugar puckering by NMR analyses of the starting nucleosides. Enzymatic ligation to microhelix-RNAs provide access to tRNA analogues containing a 3′ terminal A 76 locked in South conformation. Biological evaluation of our tRNA analogues has been performed using amino-acyl tRNA-dependent transferase FemXWv, which mediates non-ribosomal incorporation of amino acids into the bacterial cell wall. We have shown that our tRNA analogues inhibited the aminoacyl transfer reaction catalyzed by FemXWv with IC50s of 10 and 8 μM. These results indicate that FemXWv displays a moderate preference for tRNAs containing a terminal A 76 locked in the South conformation and that a South to North switch in the conformation of the terminal ribose might contribute to the release of the uncharged tRNA Ala product of the aminoacyl transfer reaction catalyzed by FemXwv .