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Namehelp_outline
4-demethylwyosine37 in tRNAPhe
Identifier
RHEA-COMP:10164
Reactive part
help_outline
- Name help_outline 4-demethylwyosine residue Identifier CHEBI:64315 Charge -1 Formula C13H13N5O7P Positionhelp_outline 37 SMILEShelp_outline O(P(=O)(*)[O-])C[C@H]1O[C@@H](N2C=3N=C4N(C(=O)C3N=C2)C=C(N4)C)[C@@H]([C@@H]1O*)O 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline S-adenosyl-L-methionine Identifier CHEBI:59789 Charge 1 Formula C15H23N6O5S InChIKeyhelp_outline MEFKEPWMEQBLKI-AIRLBKTGSA-O SMILEShelp_outline C[S+](CC[C@H]([NH3+])C([O-])=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1cnc2c(N)ncnc12 2D coordinates Mol file for the small molecule Search links Involved in 868 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,431 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
isowyosine37 in tRNAPhe
Identifier
RHEA-COMP:13445
Reactive part
help_outline
- Name help_outline isowyosine 5'-monophosphate residue Identifier CHEBI:136979 Charge -1 Formula C14H15N5O7P SMILEShelp_outline C1(=C(N2C(=O)C3=C(NC2=N1)N(C=N3)[C@@H]4O[C@H](COP(=O)(*)[O-])[C@@H](O*)[C@H]4O)C)C 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline S-adenosyl-L-homocysteine Identifier CHEBI:57856 Charge 0 Formula C14H20N6O5S InChIKeyhelp_outline ZJUKTBDSGOFHSH-WFMPWKQPSA-N SMILEShelp_outline Nc1ncnc2n(cnc12)[C@@H]1O[C@H](CSCC[C@H]([NH3+])C([O-])=O)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 792 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
RHEA:53056 | RHEA:53057 | RHEA:53058 | RHEA:53059 | |
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Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
UniProtKB help_outline |
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MetaCyc help_outline |
Publications
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Biosynthesis of wyosine derivatives in tRNA: an ancient and highly diverse pathway in Archaea.
de Crecy-Lagard V., Brochier-Armanet C., Urbonavicius J., Fernandez B., Phillips G., Lyons B., Noma A., Alvarez S., Droogmans L., Armengaud J., Grosjean H.
Wyosine (imG) and its derivatives such as wybutosine (yW) are found at position 37 of phenylalanine-specific transfer RNA (tRNA(Phe)), 3' adjacent to the anticodon in Eucarya and Archaea. In Saccharomyces cerevisiae, formation of yW requires five enzymes acting in a strictly sequential order: Trm5 ... >> More
Wyosine (imG) and its derivatives such as wybutosine (yW) are found at position 37 of phenylalanine-specific transfer RNA (tRNA(Phe)), 3' adjacent to the anticodon in Eucarya and Archaea. In Saccharomyces cerevisiae, formation of yW requires five enzymes acting in a strictly sequential order: Trm5, Tyw1, Tyw2, Tyw3, and Tyw4. Archaea contain wyosine derivatives, but their diversity is greater than in eukaryotes and the corresponding biosynthesis pathways still unknown. To identify these pathways, we analyzed the phylogenetic distribution of homologues of the yeast wybutosine biosynthesis proteins in 62 archaeal genomes and proposed a scenario for the origin and evolution of wyosine derivatives biosynthesis in Archaea that was partly experimentally validated. The key observations were 1) that four of the five wybutosine biosynthetic enzymes are ancient and may have been present in the last common ancestor of Archaea and Eucarya, 2) that the variations in the distribution pattern of biosynthesis enzymes reflect the diversity of the wyosine derivatives found in different Archaea. We also identified 7-aminocarboxypropyl-demethylwyosine (yW-86) and its N4-methyl derivative (yW-72) as final products in tRNAs of several Archaea when these were previously thought to be only intermediates of the eukaryotic pathway. We confirmed that isowyosine (imG2) and 7-methylwyosine (mimG) are two archaeal-specific guanosine-37 derivatives found in tRNA of both Euryarchaeota and Crenarchaeota. Finally, we proposed that the duplication of the trm5 gene in some Archaea led to a change in function from N1 methylation of guanosine to C7 methylation of 4-demethylwyosine (imG-14). << Less
Mol. Biol. Evol. 27:2062-2077(2010) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.
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Evolution of tRNAPhe:imG2 methyltransferases involved in the biosynthesis of wyosine derivatives in Archaea.
Urbonavicius J., Rutkiene R., Lopato A., Tauraite D., Stankeviciute J., Aucynaite A., Kaliniene L., van Tilbeurgh H., Meskys R.
Tricyclic wyosine derivatives are found at position 37 of eukaryotic and archaeal tRNA<sup>Phe</sup> In Archaea, the intermediate imG-14 is targeted by three different enzymes that catalyze the formation of yW-86, imG, and imG2. We have suggested previously that a peculiar methyltransferase (aTrm5 ... >> More
Tricyclic wyosine derivatives are found at position 37 of eukaryotic and archaeal tRNA<sup>Phe</sup> In Archaea, the intermediate imG-14 is targeted by three different enzymes that catalyze the formation of yW-86, imG, and imG2. We have suggested previously that a peculiar methyltransferase (aTrm5a/Taw22) likely catalyzes two distinct reactions: N<sup>1</sup>-methylation of guanosine to yield m<sup>1</sup>G; and C<sup>7</sup>-methylation of imG-14 to yield imG2. Here we show that the recombinant aTrm5a/Taw22-like enzymes from both Pyrococcus abyssi and Nanoarchaeum equitans indeed possess such dual specificity. We also show that substitutions of individual conservative amino acids of P. abyssi Taw22 (P260N, E173A, and R174A) have a differential effect on the formation of m<sup>1</sup>G/imG2, while replacement of R134, F165, E213, and P262 with alanine abolishes the formation of both derivatives of G37. We further demonstrate that aTrm5a-type enzyme SSO2439 from Sulfolobus solfataricus, which has no N<sup>1</sup>-methyltransferase activity, exhibits C<sup>7</sup>-methyltransferase activity, thereby producing imG2 from imG-14. We thus suggest renaming such aTrm5a methyltransferases as Taw21 to distinguish between monofunctional and bifunctional aTrm5a enzymes. << Less
RNA 22:1871-1883(2016) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.