Synthesis and Structure Elucidation of Glutamyl-Queuosine
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.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:145 |
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| Enthalten in: |
Journal of the American Chemical Society - 145(2023), 47 vom: 29. Nov., Seite 25528-25532 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Pichler, Alexander [VerfasserIn] |
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| Links: |
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| Themen: |
57072-36-3 |
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| Anmerkungen: |
Date Completed 30.11.2023 Date Revised 14.02.2024 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1021/jacs.3c10075 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM364594209 |
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| 520 | |a 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 | ||
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| 700 | 1 | |a Hillmeier, Markus |e verfasserin |4 aut | |
| 700 | 1 | |a Heiss, Matthias |e verfasserin |4 aut | |
| 700 | 1 | |a Peev, Elsa |e verfasserin |4 aut | |
| 700 | 1 | |a Xefteris, Stylianos |e verfasserin |4 aut | |
| 700 | 1 | |a Steigenberger, Barbara |e verfasserin |4 aut | |
| 700 | 1 | |a Thoma, Ines |e verfasserin |4 aut | |
| 700 | 1 | |a Müller, Markus |e verfasserin |4 aut | |
| 700 | 1 | |a Borsò, Marco |e verfasserin |4 aut | |
| 700 | 1 | |a Imhof, Axel |e verfasserin |4 aut | |
| 700 | 1 | |a Carell, Thomas |e verfasserin |4 aut | |
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