title: Synthesis of 3'-triazoyl-dinucleotides as precursors of stable Phe-tRNA(Phe) and Leu-tRNA(Leu) analogues.
abstract: We report here the synthesis of stable Phe-tRNA(Phe) and Leu-tRNA(Leu) analogues containing a 1,2,3-triazole ring instead of the ribose-amino acid ester bond. The 1,2,3-triazole ring is generated by dipolar cycloaddition of alkyne Phe and Leu analogues to 3'-azido-3'-deoxyadenosine via the Cu(I)-catalysed Huisgen, Meldal, Sharpless 1,3-cycloaddition. The corresponding triazoyl pdCpA dinucleotides, obtained by classical phosphoramidite chemistry, were enzymatically ligated to 22-nt or 74-nt RNA generating stable Phe-tRNA(Phe) analogues containing the acceptor stem or full tRNA moieties, respectively. These molecules represent useful tools to study the contribution of the RNA and amino acid moieties in stabilization of aminoacyl-tRNA/protein complexes.
authors.affiliation: Institut Parisien de Chimie Moléculaire, CNRS UMR 7201, Université Pierre et Marie Curie Paris 6, 4, place Jussieu, 75005 Paris, France.
authors.forename: Marco
authors.initials: M
authors.lastname: Santarem
authors.affiliation: Centre de Recherche des Cordeliers, LRMA, Equipe 12, INSERM UMR S 1138, Université Pierre et Marie Curie-Paris 6, UMR S 1138, Paris F-75006, France; Université Paris Descartes, Sorbonne Paris Cité, UMR S 1138, Paris F-75006 France.
authors.forename: Matthieu
authors.initials: M
authors.lastname: Fonvielle
authors.affiliation: Chemistry & Biology Nucleo(s)tides & Immunology for Therapy (CBNIT), CNRS UMR8601, Université Paris Descartes, PRES Sorbonne Paris Cité, 45 rue des Saints-Pères, 75270 Paris Cedex 06, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Sakkas
authors.affiliation: Chemistry & Biology Nucleo(s)tides & Immunology for Therapy (CBNIT), CNRS UMR8601, Université Paris Descartes, PRES Sorbonne Paris Cité, 45 rue des Saints-Pères, 75270 Paris Cedex 06, France.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Laisné
authors.affiliation: Institut Parisien de Chimie Moléculaire, CNRS UMR 7201, Université Pierre et Marie Curie Paris 6, 4, place Jussieu, 75005 Paris, France.
authors.forename: Maryline
authors.initials: M
authors.lastname: Chemama
authors.affiliation: Chemistry & Biology Nucleo(s)tides & Immunology for Therapy (CBNIT), CNRS UMR8601, Université Paris Descartes, PRES Sorbonne Paris Cité, 45 rue des Saints-Pères, 75270 Paris Cedex 06, France.
authors.forename: Jean-Philippe
authors.initials: JP
authors.lastname: Herbeuval
authors.affiliation: Chemistry & Biology Nucleo(s)tides & Immunology for Therapy (CBNIT), CNRS UMR8601, Université Paris Descartes, PRES Sorbonne Paris Cité, 45 rue des Saints-Pères, 75270 Paris Cedex 06, France.
authors.forename: Emmanuelle
authors.initials: E
authors.lastname: Braud
authors.affiliation: Centre de Recherche des Cordeliers, LRMA, Equipe 12, INSERM UMR S 1138, Université Pierre et Marie Curie-Paris 6, UMR S 1138, Paris F-75006, France; Université Paris Descartes, Sorbonne Paris Cité, UMR S 1138, Paris F-75006 France.
authors.forename: Michel
authors.initials: M
authors.lastname: Arthur
authors.affiliation: Chemistry & Biology Nucleo(s)tides & Immunology for Therapy (CBNIT), CNRS UMR8601, Université Paris Descartes, PRES Sorbonne Paris Cité, 45 rue des Saints-Pères, 75270 Paris Cedex 06, France. Electronic address: melanie.etheve-quelquejeu@parisdescartes.fr.
authors.forename: Mélanie
authors.initials: M
authors.lastname: Etheve-Quelquejeu
mesh_terms: D008958:Models, Molecular; D008968:Molecular Conformation; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D012356:RNA, Transfer, Leu / Q000138:chemical synthesis / Q000737:chemistry*; D012360:RNA, Transfer, Phe / Q000138:chemical synthesis / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D009711:Nucleotides; D012356:RNA, Transfer, Leu; D012360:RNA, Transfer, Phe; D014230:Triazoles
keywords: Aminoacyl-tRNA; Click chemistry; Cycloaddition; Cyclodipeptides synthases; Dinucleotides