Queuosin

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Structural formula
Structural formula of queuosine
General
Surname Queuosin
other names
  • Q (short code)
  • 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
Molecular formula C 17 H 23 N 5 O 7
External identifiers / databases
CAS number 57072-36-3
PubChem 42119
ChemSpider 38409
Wikidata Q425950
properties
Molar mass 409.39 g mol −1
Physical state

firmly

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Queuosine (Q) is a rare nucleoside and occurs in the tRNA of bacteria and eukaryotes . It consists of the β- D ribofuranose (sugar) and the queuin . Like archaeosine, it is structurally derived from guanosine . The N 7 atom of guanine is replaced by a C 7 atom and thus forms 7-deazaguanosine , to which further substituents can be added.

Queuosine was first found in a tRNA from E. coli in 1968 ; it is found in the anticodon at position 34 and occupies the wobble position for histidine , aspartic acid , asparagine and tyrosine . The cyclopentene ring of the queuosine protrudes from the anticodon and thus does not hinder the base pairing with the codon of the mRNA . There is the possibility of hydrogen bonds between the hydroxyl groups of the cyclopentene ring and the oxygen atoms of the ribose of the uracil at position 33. If one compares the bond strengths between codon and anticodon (guanosine or queuosine at position 34), it can be observed that guanosine is its usual partner C preferred. The queuosin can no longer differentiate between C and U.

literature

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ↑ D. Iwata-Reuyl: Biosynthesis of the 7-deazaguanosine hypermodified nucleosides of transfer RNA ; Bioorg. Chem. , 2003 , 31  (1), pp. 24-43 ( doi : 10.1016 / S0045-2068 (02) 00513-8 ; PMID 12697167 ).
  3. ^ RC Morris, MS Elliott: Queuosine modification of tRNA: a case for convergent evolution ; Mol. Genet. Metab. , 2001 , 74  (1-2), pp. 147-159 ( doi : 10.1006 / mgme.2001.3216 ; PMID 11592812 ).
  4. ↑ F. Harada, S. Nishimura: 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 , 1972 , 11  (2), pp. 301-308 ( doi : 10.1021 / bi00752a024 ; PMID 4550561 ).
  5. ^ RC Morris, KG Brown, MS Elliott: The Effect of Queuosine on tRNA Structure and Function ; J. Biomol. Struct. Dyn. , 1999 , 16  (4), pp. 757-774 ( doi : 10.1080 / 07391102.1999.10508291 ; PMID 10217448 ).
  6. ↑ F. Meier, B. Suter, H. Grosjean, G. Keith, E. Kubli: Queuosine modification of the wobble base in tRNA His influences 'in vivo' decoding properties ; EMBO J. , 1985 , 4  (3), pp. 823-827 ( PMC 554263 (free full text); PMID 2988936 ).
  7. ↑ M. Bienz, E. Kubli: Wild-type tRNA Tyr G reads the TMV RNA stop codon, but Q base-modified tRNA Tyr Q does not ; Nature , 1981 , 294 , pp. 188-190 ( doi : 10.1038 / 294188a0 ).
  8. ↑ J. Urbonavicius, Q. Qian, JM Durand, TG Hagervall, GR Björk: Improvement of reading frame maintenance is a common function for several tRNA modifications ; EMBO J. , 2001 , 20  (17), pp. 4863-4873 ( doi : 10.1093 / emboj / 20.17.4863 ; PMC 125605 (free full text); PMID 11532950 ).

Web links

  • Entry on Queuosine in the Human Metabolome Database (HMDB) , accessed June 12, 2019.
  • Modification Summary of Queuosine in Modomics database, accessed on June 12 of 2019.