Queuosine

Queuosine
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Names
	IUPAC name 2-Amino-5-[[[(1S,4S,5R)- 4,5-dihydroxy-1-cyclopent- 2-enyl]amino]methyl]- 7-[(2R,3R,4S,5R)- 3,4-dihydroxy-5-(hydroxymethyl)- 2-tetrahydrofuranyl]- 1H-pyrrolo[3,2-e]pyrimidin-4-one
Identifiers
CAS Number	57072-36-3
ChemSpider	38409
Jmol 3D model	Interactive image
PubChem	42119
	InChI InChI=1S/C17H23N5O7/c18-17-20-14-10(15(28)21-17)6(3-19-7-1-2-8(24)11(7)25)4-22(14)16-13(27)12(26)9(5-23)29-16/h1-2,4,7-9,11-13,16,19,23-27H,3,5H2,(H3,18,20,21,28)/t7-,8-,9+,11+,12+,13+,16+/m0/s1 Key: QQXQGKSPIMGUIZ-AEZJAUAXSA-N ; InChI=1/C17H23N5O7/c18-17-20-14-10(15(28)21-17)6(3-19-7-1-2-8(24)11(7)25)4-22(14)16-13(27)12(26)9(5-23)29-16/h1-2,4,7-9,11-13,16,19,23-27H,3,5H2,(H3,18,20,21,28)/t7-,8-,9+,11+,12+,13+,16+/m0/s1 Key: QQXQGKSPIMGUIZ-AEZJAUAXBO ;
	SMILES C1=C[C@@H]([C@@H]([C@H]1NCC2=CN(C3=C2C(=O)N=C(N3)N)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O)O)O ;
Properties
Chemical formula	C17H23N5O7
Molar mass	409.39 g/mol
Vapor pressure	{{{value}}}
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Queuosine is a modified nucleoside that is present in certain tRNAs in bacteria and eukaryotes.^[1]^[2] Originally identified in E. coli, queuosine was found to occupy the first anticodon position of tRNAs for histidine, aspartic acid, asparagine and tyrosine.^[3] The first anticodon position pairs with the third "wobble" position in codons, and queuosine improves accuracy of translation.^[4]^[5]^[6] Synthesis of queuosine begins with GTP. In bacteria, two classes of riboswitch are known to regulate genes that are involved in the synthesis or transport of pre-queuosine₁, a precursor to queuosine: PreQ1-I riboswitches and PreQ1-II riboswitches.

References

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.