Synthesis and Structure Elucidation of Glutamyl-Queuosine

Pichler, Alexander ; Hillmeier, Markus; Heiss, Matthias ; Peev, Elsa; Xefteris, Stylianos; Steigenberger, Barbara; Thoma, Ines; Müller, Markus ; Borso, Marco ; Imhof, Axel und Carell, Thomas (15. November 2023): Synthesis and Structure Elucidation of Glutamyl-Queuosine. In: Journal of the American Chemical Society, Bd. 145, Nr. 47: S. 25528-25532

Abstract

Queuosine is one of the most complex hypermodified RNA nucleosides found in the Wobble position of tRNAs. In addition to Queuosine itself, several further modified derivatives are known, where the cyclopentene ring structure is additionally modified by a galactosyl-, a mannosyl-, or a glutamyl-residue. While sugar-modified Queuosine derivatives are found in the tRNAs of vertebrates, glutamylated Queuosine (gluQ) is only known in bacteria. The exact structure of gluQ, particularly with respect to how and where the glutamyl side chain is connected to the Queuosine cyclopentene side chain, is unknown. Here we report the first synthesis of gluQ and, using UHPLC-MS-coinjection and NMR studies, we show that the isolated natural gluQ is the α-allyl-connected gluQ compound.

• Dokumententyp: Zeitschriftenartikel
• EU Funded Grant Agreement Number: 861381
• EU-Projekte: Horizon 2020 > ERC Grants > ERC Advanced Grant > ERC Grant 741912: EPiR - The Chemical Basis of RNA Epigenetics
• Publikationsform: Publisher's Version
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 0002-7863
• Sprache: Englisch

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