Queuine
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| Names | |
|---|---|
| Other names
7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanine | |
| Identifiers | |
72496-59-4  | |
| 3D model (Jmol) | Interactive image |
| ChemSpider | 102837  |
| MeSH | Queuine |
| PubChem | 114881 |
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| |
| Properties | |
| C12H15N5O3 | |
| Molar mass | 277.28 g/mol |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
Queuine (Q) is a hypermodified nucleobase found in the first (or wobble) position of the anticodon of tRNAs specific for Asn, Asp, His, and Tyr, in most eukaryotes and prokaryotes.
The nucleoside of queuine is queuosine. Queuine is not found in the tRNA of archaea; however, a related 7-deazaguanine derivative, the nucleoside of which is archaeosine, occurs in different tRNA position, the dihydrouridine loop, and in tRNAs with more specificities.
Literature
- Walter R. Farkas: „Queuine, The Q-Containing tRNAs and the Enzymes Responsible for Their Formation“, Nucleosides, Nucleotides & Nucleic Acids, 1983, 2 (1), pp. 1–20 (doi:10.1080/07328318308078845).
- Hiroshi Akimoto, Eiko Imamiya, Takenori Hitaka, Hiroaki Nomura, Susumu Nishimura: „Synthesis of Queuine, the Base of Naturally Occurring Hypermodified Nucleoside (Queuosine), and Its Analogues“, J. Chem. Soc., Perkin Trans. 1, 1988, pp. 1637–1644 (doi:10.1039/P19880001637).
- Charles J. Barnett, Lana M. Grubb: „Total Synthesis of Q-Base (Queuine)“, Tetrahedron, 2000, 56 (47), pp. 9221–9225 (doi:10.1016/S0040-4020(00)00895-4).
- Florian Klepper: Synthese der natürlichen tRNA Nukleosidmodifikationen Queuosin und Archaeosin, Dissertation, München 2007 (PDF; 5,1 MB), pp. 25–28.
- Allen F. Brooks, George A. Garcia, H. D. Hollis Showalter: „A Short, Concise Synthesis of Queuine“, Tetrahedron Letters, 2010, 51 (32), pp. 4163–4165 (doi:10.1016/j.tetlet.2010.06.008; PDF).
External links
- Human Metabolome Database: Queuine (HMDB01495)
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