Queuosine

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Contents

Queuosine
Queuosine - Queuosin.svg
Names
Preferred IUPAC name
7-({[(1S,4S,5R)-4,5-Dihydroxycyclopent-2-en-1-yl]amino}methyl)-7-carbaguanosine
Systematic IUPAC name
2-Amino-5-({[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • 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 X mark.svgN
    Key: QQXQGKSPIMGUIZ-AEZJAUAXSA-N X mark.svgN
  • 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
  • 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
C17H23N5O7
Molar mass 409.399 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Queuosine is a modified nucleoside that is present in certain tRNAs in bacteria and eukaryotes. [1] [2] It contains the nucleobase queuine. 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 compared to guanosine. [4] [5] [6] Synthesis of queuosine begins with GTP. In bacteria, three structurally unrelated 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, PreQ1-II riboswitches and PreQ1-III riboswitches.

Queuosine biosynthesis genes have also been found on phage genomes and may be involved in protection from genome degradation by the host. [7] [8]

References

  1. Iwata-Reuyl D (February 2003). "Biosynthesis of the 7-deazaguanosine hypermodified nucleosides of transfer RNA". Bioorganic Chemistry. 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". Molecular Genetics and Metabolism. 74 (1–2): 147–159. doi:10.1006/mgme.2001.3216. PMID   11592812.
  3. Harada F, Nishimura S (January 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): 301–308. doi:10.1021/bi00752a024. PMID   4550561.
  4. Bienz M, Kubli E (November 1981). "Wild-type tRNATyrG reads the TMV RNA stop codon, but Q base-modified tRNATyrQ does not". Nature. 294 (5837): 188–190. Bibcode:1981Natur.294..188B. doi:10.1038/294188a0. PMID   29451243. S2CID   204999725.
  5. Meier F, Suter B, Grosjean H, Keith G, Kubli E (March 1985). "Queuosine modification of the wobble base in tRNAHis influences 'in vivo' decoding properties". The EMBO Journal. 4 (3): 823–827. doi:10.1002/j.1460-2075.1985.tb03704.x. PMC   554263 . PMID   2988936.
  6. Urbonavicius J, Qian Q, Durand JM, Hagervall TG, Björk GR (September 2001). "Improvement of reading frame maintenance is a common function for several tRNA modifications". The EMBO Journal. 20 (17): 4863–4873. doi:10.1093/emboj/20.17.4863. PMC   125605 . PMID   11532950.
  7. Sazinas P, Redgwell T, Rihtman B, Grigonyte A, Michniewski S, Scanlan DJ, et al. (January 2018). "Comparative Genomics of Bacteriophage of the Genus Seuratvirus". Genome Biology and Evolution. 10 (1): 72–76. doi:10.1063/5.0085058.7. PMC   5758909 . PMID   29272407.
  8. Sabri M, Häuser R, Ouellette M, Liu J, Dehbi M, Moeck G, et al. (January 2011). "Genome annotation and intraviral interactome for the Streptococcus pneumoniae virulent phage Dp-1". Journal of Bacteriology. 193 (2): 551–562. doi:10.1128/JB.01117-10. PMC   3019816 . PMID   21097633.

Further reading