Queuosine

Chembox new
ImageFile=Queuosine.pngImageSize=200px
IUPACName=2-Amino-5- [(1"S",4"S",5"R")-4,5-dihydroxy-1-cyclopent-2-enyl] amino] methyl] -7- [(2"R",3"R",4"S",5"R")-3,4-dihydroxy-5-(hydroxymethyl)-2-tetrahydrofuranyl] -1"H"-pyrrolo [3,2-e] pyrimidin-4-one
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Section1= Chembox Identifiers
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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
Section2= Chembox Properties
Formula=C₁₇H₂₃N₅O₇
MolarMass=409.39 g/mol
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Section3= Chembox Hazards
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Queuosine is a modified nucleoside that is present in certain tRNAs in bacteria and eukaryotes. [cite journal |author=Iwata-Reuyl D |title=Biosynthesis of the 7-deazaguanosine hypermodified nucleosides of transfer RNA |journal=Bioorg. Chem. |volume=31 |issue=1 |pages=24–43 |year=2003 |pmid=12697167 |doi=] [cite journal |author=Morris RC, Elliott MS |title=Queuosine modification of tRNA: a case for convergent evolution |journal=Mol. Genet. Metab. |volume=74 |issue=1-2 |pages=147–59 |year=2001 |pmid=11592812 |doi=10.1006/mgme.2001.3216] Originally identified in "E. coli", queuosine was found to occupy the first anticodon position of tRNAs for histidine, aspartic acid, asparagine and tyrosine. [cite journal |author=Harada F, Nishimura S |title=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 |journal=Biochemistry |volume=11 |issue=2 |pages=301–8 |year=1972 |pmid=4550561 |doi=] The first anticodon position pairs with the third "wobble" position in codons, and queuosine improves accuracy of translation. [cite journal |author=Bienz M and Kubli E|title=Wild-type tRNATyrG reads the TMV RNA stop codon, but Q base-modified tRNATyrQ does not |journal=Nature|volume=294 |pages=188–190 |year=1981 |doi=10.1038/294188a0] [cite journal |author=Meier F, Suter B, Grosjean H, Keith G, Kubli E |title=Queuosine modification of the wobble base in tRNAHis influences 'in vivo' decoding properties |journal=EMBO J. |volume=4 |issue=3 |pages=823–7 |year=1985 |pmid=2988936 |doi=] [cite journal |author=Urbonavicius J, Qian Q, Durand JM, Hagervall TG, Björk GR |title=Improvement of reading frame maintenance is a common function for several tRNA modifications |journal=EMBO J. |volume=20 |issue=17 |pages=4863–73 |year=2001 |pmid=11532950 |doi=10.1093/emboj/20.17.4863] 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.

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