Reaction participants Show >> << Hide
- Name help_outline FMN Identifier CHEBI:58210 Charge -3 Formula C17H18N4O9P InChIKeyhelp_outline ANKZYBDXHMZBDK-SCRDCRAPSA-K SMILEShelp_outline C12=NC([N-]C(C1=NC=3C(N2C[C@@H]([C@@H]([C@@H](COP(=O)([O-])[O-])O)O)O)=CC(=C(C3)C)C)=O)=O 2D coordinates Mol file for the small molecule Search links Involved in 789 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 9,331 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline oxidized coenzyme F420-0 Identifier CHEBI:59907 Charge -3 Formula C19H19N3O12P InChIKeyhelp_outline OLEQJMXJEZZMHZ-GQPBWUKJSA-K SMILEShelp_outline C[C@H](OP([O-])(=O)OC[C@@H](O)[C@@H](O)[C@@H](O)Cn1c2cc(O)ccc2cc2c1nc(=O)[n-]c2=O)C([O-])=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 dehydro coenzyme F420-0 Identifier CHEBI:143705 Charge -3 Formula C19H17N3O12P InChIKeyhelp_outline TVDWUIWMKSEGKW-ZNMIVQPWSA-K SMILEShelp_outline C1=2N(C3=CC(=CC=C3C=C1C([N-]C(N2)=O)=O)O)C[C@@H]([C@@H]([C@@H](COP(OC(C([O-])=O)=C)(=O)[O-])O)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 FMNH2 Identifier CHEBI:57618 (Beilstein: 6258176) help_outline Charge -2 Formula C17H21N4O9P InChIKeyhelp_outline YTNIXZGTHTVJBW-SCRDCRAPSA-L SMILEShelp_outline Cc1cc2Nc3c([nH]c(=O)[nH]c3=O)N(C[C@H](O)[C@H](O)[C@H](O)COP([O-])([O-])=O)c2cc1C 2D coordinates Mol file for the small molecule Search links Involved in 779 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
RHEA:60360 | RHEA:60361 | RHEA:60362 | RHEA:60363 | |
---|---|---|---|---|
Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
UniProtKB help_outline |
|
|||
EC numbers help_outline | ||||
MetaCyc help_outline |
Publications
-
A revised biosynthetic pathway for the cofactor F420 in prokaryotes.
Bashiri G., Antoney J., Jirgis E.N.M., Shah M.V., Ney B., Copp J., Stuteley S.M., Sreebhavan S., Palmer B., Middleditch M., Tokuriki N., Greening C., Scott C., Baker E.N., Jackson C.J.
Cofactor F<sub>420</sub> plays critical roles in primary and secondary metabolism in a range of bacteria and archaea as a low-potential hydride transfer agent. It mediates a variety of important redox transformations involved in bacterial persistence, antibiotic biosynthesis, pro-drug activation a ... >> More
Cofactor F<sub>420</sub> plays critical roles in primary and secondary metabolism in a range of bacteria and archaea as a low-potential hydride transfer agent. It mediates a variety of important redox transformations involved in bacterial persistence, antibiotic biosynthesis, pro-drug activation and methanogenesis. However, the biosynthetic pathway for F<sub>420</sub> has not been fully elucidated: neither the enzyme that generates the putative intermediate 2-phospho-L-lactate, nor the function of the FMN-binding C-terminal domain of the γ-glutamyl ligase (FbiB) in bacteria are known. Here we present the structure of the guanylyltransferase FbiD and show that, along with its archaeal homolog CofC, it accepts phosphoenolpyruvate, rather than 2-phospho-L-lactate, as the substrate, leading to the formation of the previously uncharacterized intermediate dehydro-F<sub>420</sub>-0. The C-terminal domain of FbiB then utilizes FMNH<sub>2</sub> to reduce dehydro-F<sub>420</sub>-0, which produces mature F<sub>420</sub> species when combined with the γ-glutamyl ligase activity of the N-terminal domain. These new insights have allowed the heterologous production of F<sub>420</sub> from a recombinant F<sub>420</sub> biosynthetic pathway in Escherichia coli. << Less
Nat. Commun. 10:1558-1558(2019) [PubMed] [EuropePMC]
This publication is cited by 5 other entries.