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Name^help_outline tRNA^Pyl Identifier RHEA-COMP:9720 Reactive part ^help_outline
- Name ^help_outline AMP 3'-end residue Identifier CHEBI:78442 Charge -1 Formula C10H12N5O6P SMILES^help_outline Nc1ncnc2n(cnc12)[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 76 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Search links Involved in 1 reaction(s) Find proteins in UniProtKB for this molecule
Name ^help_outline L-pyrrolysine Identifier CHEBI:58499 Charge 0 Formula C12H21N3O3 InChIKey^help_outline ZFOMKMMPBOQKMC-KXUCPTDWSA-N SMILES^help_outline C[C@@H]1CC=N[C@H]1C(=O)NCCCC[C@H]([NH3+])C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline ATP Identifier CHEBI:30616 (Beilstein: 3581767) ^help_outline Charge -4 Formula C10H12N5O13P3 InChIKey^help_outline ZKHQWZAMYRWXGA-KQYNXXCUSA-J SMILES^help_outline Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,284 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name^help_outline L-pyrrolysyl-tRNA^Pyl Identifier RHEA-COMP:9721 Reactive part ^help_outline
- Name ^help_outline 3'-(L-pyrrolysyl)adenylyl group Identifier CHEBI:78556 Charge 0 Formula C22H32N8O8P SMILES^help_outline C[C@@H]1CC=N[C@H]1C(=O)NCCCC[C@H]([NH3+])C(=O)O[C@@H]1[C@@H](COP([O-])(-*)=O)O[C@H]([C@@H]1O)n1cnc2c(N)ncnc12 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
Search links Involved in 1 reaction(s) Find proteins in UniProtKB for this molecule
Name ^help_outline AMP Identifier CHEBI:456215 Charge -2 Formula C10H12N5O7P InChIKey^help_outline UDMBCSSLTHHNCD-KQYNXXCUSA-L SMILES^help_outline Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 512 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline diphosphate Identifier CHEBI:33019 (Beilstein: 185088) ^help_outline Charge -3 Formula HO7P2 InChIKey^help_outline XPPKVPWEQAFLFU-UHFFFAOYSA-K SMILES^help_outline OP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 1,139 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule

Cross-references

	RHEA:19277	RHEA:19278	RHEA:19279	RHEA:19280
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline	73 proteins
EC numbers ^help_outline	6.1.1.26
Gene Ontology ^help_outline	GO:0043767
KEGG ^help_outline				R08578
MetaCyc ^help_outline		6.1.1.26-RXN

Publications

Angiographic appearance of renal papillary-tubular adenocarcinomas.

Weiss R.M., Becker J.A., Davidson A.J., Lytton B.

J Urol 102:661-664(1969) [PubMed] [EuropePMC]
Molecular biology: genetic code seizes pyrrolysine.

Schimmel P., Beebe K.

Nature 431:257-258(2004) [PubMed] [EuropePMC]
Direct charging of tRNA(CUA) with pyrrolysine in vitro and in vivo.

Blight S.K., Larue R.C., Mahapatra A., Longstaff D.G., Chang E., Zhao G., Kang P.T., Green-Church K.B., Chan M.K., Krzycki J.A.

Pyrrolysine is the 22nd amino acid. An unresolved question has been how this atypical genetically encoded residue is inserted into proteins, because all previously described naturally occurring aminoacyl-tRNA synthetases are specific for one of the 20 universally distributed amino acids. Here we e ... >> More

Pyrrolysine is the 22nd amino acid. An unresolved question has been how this atypical genetically encoded residue is inserted into proteins, because all previously described naturally occurring aminoacyl-tRNA synthetases are specific for one of the 20 universally distributed amino acids. Here we establish that synthetic L-pyrrolysine is attached as a free molecule to tRNA(CUA) by PylS, an archaeal class II aminoacyl-tRNA synthetase. PylS activates pyrrolysine with ATP and ligates pyrrolysine to tRNA(CUA) in vitro in reactions specific for pyrrolysine. The addition of pyrrolysine to Escherichia coli cells expressing pylT (encoding tRNA(CUA)) and pylS results in the translation of UAG in vivo as a sense codon. This is the first example from nature of direct aminoacylation of a tRNA with a non-canonical amino acid and shows that the genetic code of E. coli can be expanded to include UAG-directed pyrrolysine incorporation into proteins. << Less

Nature 431:333-335(2004) [PubMed] [EuropePMC]
An aminoacyl-tRNA synthetase that specifically activates pyrrolysine.

Polycarpo C., Ambrogelly A., Berube A., Winbush S.M., McCloskey J.A., Crain P.F., Wood J.L., Soell D.

Pyrrolysine, the 22nd cotranslationally inserted amino acid, was found in the Methanosarcina barkeri monomethylamine methyltransferase protein in a position that is encoded by an in-frame UAG stop codon in the mRNA. M. barkeri encodes a special amber suppressor tRNA (tRNA(Pyl)) that presumably rec ... >> More

Pyrrolysine, the 22nd cotranslationally inserted amino acid, was found in the Methanosarcina barkeri monomethylamine methyltransferase protein in a position that is encoded by an in-frame UAG stop codon in the mRNA. M. barkeri encodes a special amber suppressor tRNA (tRNA(Pyl)) that presumably recognizes this UAG codon. It was reported that Lys-tRNA(Pyl) can be formed by the aminoacyl-tRNA synthetase-like M. barkeri protein PylS [Srinivasan, G., James, C. M. & Krzycki, J. A. (2002) Science 296, 1459-1462], whereas a later article showed that Lys-tRNA(Pyl) is synthesized by the combined action of LysRS1 and LysRS2, the two different M. barkeri lysyl-tRNA synthetases. Pyrrolysyl-tRNA(Pyl) formation was presumed to result from subsequent modification of lysine attached to tRNA(Pyl). To investigate whether pyrrolysine can be directly attached to tRNA(Pyl) we chemically synthesized pyrrolysine. We show that PylS is a specialized aminoacyl-tRNA synthetase for charging pyrrolysine to tRNA(Pyl); lysine and tRNA(Lys) are not substrates of the enzyme. In view of the properties of PylS we propose to name this enzyme pyrrolysyl-tRNA synthetase. In contrast, the LysRS1:LysRS2 complex does not recognize pyrrolysine and charges tRNA(Pyl) with lysine. These in vitro data suggest that Methanosarcina cells have two pathways for acylating the suppressor tRNA(Pyl). This would ensure efficient translation of the in-frame UAG codon in case of pyrrolysine deficiency and safeguard the biosynthesis of the proteins whose genes contain this special codon. << Less

Proc. Natl. Acad. Sci. U.S.A. 101:12450-12454(2004) [PubMed] [EuropePMC]

RHEA:19279 L-pyrrolysyl-tRNA(Pyl) + AMP + diphosphate => tRNA(Pyl) + L-pyrrolysine + ATP Reaction with net flow from right to left. help_outline

Reaction participants Show >> << Hide

Cross-references

Publications

Angiographic appearance of renal papillary-tubular adenocarcinomas.

Molecular biology: genetic code seizes pyrrolysine.

Direct charging of tRNA(CUA) with pyrrolysine in vitro and in vivo.

An aminoacyl-tRNA synthetase that specifically activates pyrrolysine.

RHEA:19279 L-pyrrolysyl-tRNA(Pyl) + AMP + diphosphate => tRNA(Pyl) + L-pyrrolysine + ATP Reaction with net flow from right to left. ^help_outline