Queuine
From Wikipedia, the free encyclopedia
| Queuine | |
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Other names
7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanine |
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| Identifiers | |
| CAS number | 72496-59-4  |
| PubChem | 114881 |
| MeSH | Queuine |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C12H15N5O3 |
| Molar mass | 277,28 g/mol |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Queuine (Q) is a hypermodified base 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.
[edit] 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.
- 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.
- Allen F. Brooks, George A. Garcia, H. D. Hollis Showalter: „A short, concise synthesis of queuine“, Tetrahedron Letters, 2010, 51, pp. 4163–4165; doi:10.1016/j.tetlet.2010.06.008; PDF.
[edit] External links
- Human Metabolome Database: Queuine (HMDB01495)
