Queuine

Queuine
Names
	Preferred IUPAC name 2-Amino-5-({[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one
	Other names 7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanine
Identifiers
CAS Number	72496-59-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	102837 ;
MeSH	Queuine
PubChem CID	114881;
UNII	DAK6EYX2BZ ;
CompTox Dashboard (EPA)	DTXSID20895854 ;
	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 Key: WYROLENTHWJFLR-ACLDMZEESA-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	277.284 g·mol−1
	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 (/kjuːiːn/) (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.^[1] Because it is utilized by all eukaryotes but produced exclusively by bacteria, it is a putative vitamin.^[2]

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.

^ Farkas, Walter R. (1983). "Queuine, the Q-Containing tRNAs and the Enzymes Responsible for Their Formation". Nucleosides and Nucleotides. 2: 1–20. doi:10.1080/07328318308078845.
^ Bjork, Glenn; Rasmusen, Torgny (1998). Modification and Editing of RNA. New York: ASM Press. p. 480. doi:10.1128/9781555818296.ch26. Whereas bacteria can synthesize the precursor preQ0, eukaryotic organisms are unable to make queuine and have to rely on the presence of the base in the diet. Queuine can therefore be considered a vitamin.

[1] Farkas, Walter R. (1983). "Queuine, the Q-Containing tRNAs and the Enzymes Responsible for Their Formation". Nucleosides and Nucleotides. 2: 1–20. doi:10.1080/07328318308078845.

[2] Bjork, Glenn; Rasmusen, Torgny (1998). Modification and Editing of RNA. New York: ASM Press. p. 480. doi:10.1128/9781555818296.ch26. Whereas bacteria can synthesize the precursor preQ0, eukaryotic organisms are unable to make queuine and have to rely on the presence of the base in the diet. Queuine can therefore be considered a vitamin.

[1]

[2]