“Queuine”的意思、由来-开放百科全书

词条

Queuine

释义

Literature
External links

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 447003644
| ImageFile=Queuine.svg
| ImageSize=240px
| IUPACName=
| OtherNames= 7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanine
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=72496-59-4
| PubChem=114881
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 102837
| SMILES = C1=C[C@@H]([C@@H]([C@H]1NCC2=CNC3=C2C(=O)NC(=N3)N)O)O
| InChI = 1/C12H15N5O3/c13-12-16-10-8(11(20)17-12)5(4-15-10)3-14-6-1-2-7(18)9(6)19/h1-2,4,6-7,9,14,18-19H,3H2,(H4,13,15,16,17,20)/t6-,7-,9+/m0/s1
| InChIKey = WYROLENTHWJFLR-ACLDMZEEBO
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C12H15N5O3/c13-12-16-10-8(11(20)17-12)5(4-15-10)3-14-6-1-2-7(18)9(6)19/h1-2,4,6-7,9,14,18-19H,3H2,(H4,13,15,16,17,20)/t6-,7-,9+/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = WYROLENTHWJFLR-ACLDMZEESA-N
| MeSHName=Queuine
|Section2={{Chembox Properties
| Formula=C₁₂H₁₅N₅O₃
| MolarMass=277.28 g/mol
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}

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: [https://web.archive.org/web/20110725015301/http://www.hmdb.ca/scripts/show_card.cgi?METABOCARD=HMDB01495 Queuine (HMDB01495)]

3 : Nucleobases|Purines|Cyclopentenes

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