Queuosine

Queuosine

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 interactive 3D	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
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

1. Iwata-Reuyl D (2003). "Biosynthesis of the 7-deazaguanosine hypermodified nucleosides of transfer RNA". Bioorg. Chem. 31 (1): 24–43. doi:10.1016/S0045-2068(02)00513-8. PMID 12697167.
2. Morris RC, Elliott MS (2001). "Queuosine modification of tRNA: a case for convergent evolution". Mol. Genet. Metab. 74 (1–2): 147–159. doi:10.1006/mgme.2001.3216. PMID 11592812.
3. Harada F, Nishimura S (1972). "Possible anticodon sequences of tRNA^His, tRNA^Asm, and tRNA^Asp from Escherichia coli B. Universal presence of nucleoside Q in the first position of the anticondons of these transfer ribonucleic acids". Biochemistry 11 (2): 301–308. doi:10.1021/bi00752a024. PMID 4550561.
4. Bienz M and Kubli E (1981). "Wild-type tRNA^Tyr_G reads the TMV RNA stop codon, but Q base-modified tRNA^Tyr_Q does not". Nature 294 (5837): 188–190. doi:10.1038/294188a0.
5. Meier F, Suter B, Grosjean H, Keith G, Kubli E (1985). "Queuosine modification of the wobble base in tRNAHis influences 'in vivo' decoding properties". EMBO J. 4 (3): 823–827. PMC 554263. PMID 2988936.
6. Urbonavicius J, Qian Q, Durand JM, Hagervall TG, Björk GR (2001). "Improvement of reading frame maintenance is a common function for several tRNA modifications". EMBO J. 20 (17): 4863–4873. doi:10.1093/emboj/20.17.4863. PMC 125605. PMID 11532950.

Literature

• 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.

External links

• Wikigenes: Queuosine
• Human Metabolome Database: Queuosine (HMDB11596)