Reaction participants Show >> << Hide
- Name help_outline 7-cyano-7-deazaguanine Identifier CHEBI:45075 (Beilstein: 5022878) help_outline Charge 0 Formula C7H5N5O InChIKeyhelp_outline FMKSMYDYKXQYRV-UHFFFAOYSA-N SMILEShelp_outline Nc1nc2[nH]cc(C#N)c2c(=O)[nH]1 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
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Namehelp_outline
guanosine15 in tRNA
Identifier
RHEA-COMP:10372
Reactive part
help_outline
- Name help_outline GMP residue Identifier CHEBI:74269 Charge -1 Formula C10H11N5O7P Positionhelp_outline 15 SMILEShelp_outline C1(=O)NC(=NC2=C1N=CN2[C@@H]3O[C@H](COP(=O)(*)[O-])[C@@H](O*)[C@H]3O)N 2D coordinates Mol file for the small molecule Search links Involved in 42 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
7-cyano-7-carbaguanosine15 in tRNA
Identifier
RHEA-COMP:10371
Reactive part
help_outline
- Name help_outline 7-cyano-7-carbaguanine 5'-phosphate residue Identifier CHEBI:82850 Charge -1 Formula C12H11N5O7P Positionhelp_outline 15 SMILEShelp_outline Nc1nc2n(cc(C#N)c2c(=O)[nH]1)[C@@H]1O[C@H](COP([O-])(-*)=O)[C@@H](O-*)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 4 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline guanine Identifier CHEBI:16235 (Beilstein: 147911; CAS: 73-40-5) help_outline Charge 0 Formula C5H5N5O InChIKeyhelp_outline UYTPUPDQBNUYGX-UHFFFAOYSA-N SMILEShelp_outline C12=C(N=C(NC1=O)N)NC=N2 2D coordinates Mol file for the small molecule Search links Involved in 16 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:43164 | RHEA:43165 | RHEA:43166 | RHEA:43167 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Hypermodification of tRNA in Thermophilic archaea. Cloning, overexpression, and characterization of tRNA-guanine transglycosylase from Methanococcus jannaschii.
Bai Y., Fox D.T., Lacy J.A., Van Lanen S.G., Iwata-Reuyl D.
tRNA is structurally unique among nucleic acids in harboring an astonishing diversity of modified nucleosides. Two structural variants of the hypermodified nucleoside 7-deazaguanosine have been identified in tRNA: queuosine, which is found at the wobble position of the anticodon in bacterial and e ... >> More
tRNA is structurally unique among nucleic acids in harboring an astonishing diversity of modified nucleosides. Two structural variants of the hypermodified nucleoside 7-deazaguanosine have been identified in tRNA: queuosine, which is found at the wobble position of the anticodon in bacterial and eukaryotic tRNA, and archaeosine, which is found at position 15 of the D-loop in archaeal tRNA. From homology searching of the Methanococcus jannaschii genome, a gene coding for an enzyme in the biosynthesis of archaeosine (tgt) was identified and cloned. The tgt gene was overexpressed in an Escherichia coli expression system, and the recombinant tRNA-guanine transglycosylase enzyme was purified and characterized. The enzyme catalyzes a transglycosylation reaction in which guanine is eliminated from position 15 of the tRNA and an archaeosine precursor (preQ(0)) is inserted. The enzyme is able to utilize both guanine and the 7-deazaguanine base preQ(0) as substrates, but not other 7-deazaguanine bases, and is able to modify tRNA from all three phylogenetic domains. The enzyme shows optimal activity at high temperature and acidic pH, consistent with the optimal growth conditions of M. jannaschii. The nature of the temperature dependence is consistent with a requirement for some degree of tRNA tertiary structure in order for recognition by the enzyme to occur. << Less