Enzymes
| UniProtKB help_outline | 11 proteins |
Reaction participants Show >> << Hide
- Name help_outline guanylylpyridinol-AMP Identifier CHEBI:234400 Charge -2 Formula C29H33N11O17P2 InChIKeyhelp_outline ADFZJYBEYBVFAY-YEASDWDASA-L SMILEShelp_outline O=C1NC(=NC2=C1N=CN2C3OC(COP(=O)([O-])OC=4C(=C(O)N=C(C4C)CC(=O)OP(=O)([O-])OCC5OC(N6C=NC=7C(=NC=NC76)N)C(O)C5O)C)C(O)C3O)N 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
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Namehelp_outline
L-cysteinyl-[protein]
Identifier
RHEA-COMP:10131
Reactive part
help_outline
- Name help_outline L-cysteine residue Identifier CHEBI:29950 Charge 0 Formula C3H5NOS SMILEShelp_outline C(=O)(*)[C@@H](N*)CS 2D coordinates Mol file for the small molecule Search links Involved in 132 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
S-guanylylpyridinol-L-cysteinyl-[protein]
Identifier
RHEA-COMP:20679
Reactive part
help_outline
- Name help_outline S-guanylylpyridinol-L-cysteine residue Identifier CHEBI:235321 Charge -1 Formula C22H25N7O11PS SMILEShelp_outline *NC(C(*)=O)CSC(=O)CC1=NC(O)=C(C(OP(=O)([O-])OCC2OC(N3C=NC=4C(=O)NC(=NC43)N)C(O)C2O)=C1C)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 AMP Identifier CHEBI:456215 Charge -2 Formula C10H12N5O7P InChIKeyhelp_outline UDMBCSSLTHHNCD-KQYNXXCUSA-L SMILEShelp_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 545 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 10,232 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:85899 | RHEA:85900 | RHEA:85901 | RHEA:85902 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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| MetaCyc help_outline |
Publications
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Protein-pyridinol thioester precursor for biosynthesis of the organometallic acyl-iron ligand in [Fe]-hydrogenase cofactor.
Fujishiro T., Kahnt J., Ermler U., Shima S.
The iron-guanylylpyridinol (FeGP) cofactor of [Fe]-hydrogenase contains a prominent iron centre with an acyl-Fe bond and is the only acyl-organometallic iron compound found in nature. Here, we identify the functions of HcgE and HcgF, involved in the biosynthesis of the FeGP cofactor using structur ... >> More
The iron-guanylylpyridinol (FeGP) cofactor of [Fe]-hydrogenase contains a prominent iron centre with an acyl-Fe bond and is the only acyl-organometallic iron compound found in nature. Here, we identify the functions of HcgE and HcgF, involved in the biosynthesis of the FeGP cofactor using structure-to-function strategy. Analysis of the HcgE and HcgF crystal structures with and without bound substrates suggest that HcgE catalyses the adenylylation of the carboxy group of guanylylpyridinol (GP) to afford AMP-GP, and subsequently HcgF catalyses the transesterification of AMP-GP to afford a Cys (HcgF)-S-GP thioester. Both enzymatic reactions are confirmed by in vitro assays. The structural data also offer plausible catalytic mechanisms. This strategy of thioester activation corresponds to that used for ubiquitin activation, a key event in the regulation of multiple cellular processes. It further implicates a nucleophilic attack onto the acyl carbon presumably via an electron-rich Fe(0)- or Fe(I)-carbonyl complex in the Fe-acyl formation. << Less
Nat. Commun. 6:6895-6895(2015) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.