Queuosine
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Names | |
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IUPAC name
2-Amino-5-[[[(1S,4S,5R)-
4,5-dihydroxy-1-cyclopent- 2-enyl]amino]methyl]- 7-[(2R,3R,4S,5R)- 3,4-dihydroxy-5-(hydroxymethyl)- 2-tetrahydrofuranyl]- 1H-pyrrolo[3,2-e]pyrimidin-4-one |
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Identifiers | |
57072-36-3 ![]() |
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ChemSpider | 38409 ![]() |
Jmol 3D model | Interactive image |
PubChem | 42119 |
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Properties | |
C17H23N5O7 | |
Molar mass | 409.39 g/mol |
Vapor pressure | {{{value}}} |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references | |
Queuosine is a modified nucleoside that is present in certain tRNAs in bacteria and eukaryotes.[1][2] Originally identified in E. coli, queuosine was found to occupy the first anticodon position of tRNAs for histidine, aspartic acid, asparagine and tyrosine.[3] The first anticodon position pairs with the third "wobble" position in codons, and queuosine improves accuracy of translation.[4][5][6] Synthesis of queuosine begins with GTP. In bacteria, two classes of riboswitch are known to regulate genes that are involved in the synthesis or transport of pre-queuosine1, a precursor to queuosine: PreQ1-I riboswitches and PreQ1-II riboswitches.
References
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Literature
- Florian Klepper: Synthese der natürlichen tRNA Nukleosidmodifikationen Queuosin und Archaeosin, Dissertation, München 2007.
- Florian Klepper, Eva-Maria Jahn, Volker Hickmann, Thomas Carell: „Synthese des tRNA-Nucleosids Queuosin unter Verwendung eines chiralen Allylazid-Intermediats", Angewandte Chemie, 2007, 119 (13), pp. 2377–2379; doi:10.1002/ange.200604579.
- Florian Klepper, Eva-Maria Jahn, Volker Hickmann, Thomas Carell: „Synthesis of the Transfer-RNA Nucleoside Queuosine by Using a Chiral Allyl Azide Intermediate", Angewandte Chemie International Edition, 2007, 46 (13), pp. 2325–2327; doi:10.1002/anie.200604579.
External links
- Wikigenes: Queuosine
- Human Metabolome Database: Queuosine (HMDB11596)
- Pages with broken file links
- Articles without EBI source
- Articles without KEGG source
- Articles without UNII source
- Articles with changed InChI identifier
- Pages using collapsible list with both background and text-align in titlestyle
- Chemical articles using a fixed chemical formula
- Nucleosides
- Pyrrolopyrimidines
- Tetrahydrofurans