Queuine

Queuine

Names
Other names 7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanine
Identifiers
CAS Number	72496-59-4 Y
3D model (Jmol)	Interactive image
ChemSpider	102837 N
MeSH	Queuine
PubChem	114881
InChI InChI=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 N Key: WYROLENTHWJFLR-ACLDMZEESA-N N 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 Key: WYROLENTHWJFLR-ACLDMZEEBO
SMILES C1=C[C@@H]([C@@H]([C@H]1NCC2=CNC3=C2C(=O)NC(=N3)N)O)O
Properties
Chemical formula	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).
N verify (what is YN ?)
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)