Queuosine

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Queuosine
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
PubChem 42119
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
Molecular formula C17H23N5O7
Molar mass 409.39 g/mol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and 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.

[edit] References

  1. ^ Iwata-Reuyl D (2003). "Biosynthesis of the 7-deazaguanosine hypermodified nucleosides of transfer RNA". Bioorg. Chem. 31 (1): 24-43. PMID 12697167. 
  2. ^ Morris RC, Elliott MS (2001). "Queuosine modification of tRNA: a case for convergent evolution". Mol. Genet. Metab. 74 (1-2): 147-59. 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 postion of the anticondons of these transfer ribonucleic acids". Biochemistry 11 (2): 301-8. PMID 4550561. 
  4. ^ Bienz M and Kubli E (1981). "Wild-type tRNATyrG reads the TMV RNA stop codon, but Q base-modified tRNATyrQ does not". Nature 294: 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): 823-7. 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): 4863-73. doi:10.1093/emboj/20.17.4863. PMID 11532950. 


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