Reaction participants Show >> << Hide
- Name help_outline (4Z,15Z)-bilirubin IXα Identifier CHEBI:57977 (Beilstein: 4083310) help_outline Charge -2 Formula C33H34N4O6 InChIKeyhelp_outline BPYKTIZUTYGOLE-IFADSCNNSA-L SMILEShelp_outline CC1=C(C=C)\C(NC1=O)=C\c1[nH]c(Cc2[nH]c(\C=C3NC(=O)C(C=C)=C/3C)c(C)c2CCC([O-])=O)c(CCC([O-])=O)c1C 2D coordinates Mol file for the small molecule Search links Involved in 10 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Name help_outline
coenzyme F420-(γ-Glu)n
Identifier
CHEBI:133980
Charge
Formula
(C5H6NO3)n.C19H19N3O12P
Search links
Involved in 17 reaction(s)
Find proteins in UniProtKB for this molecule
Form(s) in this reaction:
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Identifier: RHEA-COMP:12939Polymer name: oxidized coenzyme F420-(γ-L-Glu)(n)Polymerization index help_outline nFormula C19H19N3O12P(C5H6NO3)nCharge (-3)(-1)nMol File for the polymer
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- 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 9,521 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline biliverdin IXα Identifier CHEBI:57991 Charge -2 Formula C33H32N4O6 InChIKeyhelp_outline QBUVFDKTZJNUPP-BBROENKCSA-L SMILEShelp_outline C=1(/C=C/2\NC(=O)C(=C2C=C)C)NC(=C(C1C)CCC([O-])=O)/C=C/3\N=C(/C=C/4\NC(C(=C4C)C=C)=O)C(=C3CCC([O-])=O)C 2D coordinates Mol file for the small molecule Search links Involved in 10 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Name help_outline
reduced coenzyme F420-(γ-Glu)n
Identifier
CHEBI:139511
Charge
-3
Formula
(C5H6NO3)n.C19H22N3O12P
Search links
Involved in 16 reaction(s)
Find proteins in UniProtKB for this molecule
Form(s) in this reaction:
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Identifier: RHEA-COMP:14378Polymer name: reduced coenzyme F420-(γ-L-Glu)(n)Polymerization index help_outline nFormula C19H22N3O12P(C5H6NO3)nCharge (-2)(-1)nMol File for the polymer
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Cross-references
| RHEA:56092 | RHEA:56093 | RHEA:56094 | RHEA:56095 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Rv2074 is a novel F420H2-dependent biliverdin reductase in Mycobacterium tuberculosis.
Ahmed F.H., Mohamed A.E., Carr P.D., Lee B.M., Condic-Jurkic K., O'Mara M.L., Jackson C.J.
Bilirubin is a potent antioxidant that is produced from the reduction of the heme degradation product biliverdin. In mammalian cells and Cyanobacteria, NADH/NADPH-dependent biliverdin reductases (BVRs) of the Rossmann-fold have been shown to catalyze this reaction. Here, we describe the characteri ... >> More
Bilirubin is a potent antioxidant that is produced from the reduction of the heme degradation product biliverdin. In mammalian cells and Cyanobacteria, NADH/NADPH-dependent biliverdin reductases (BVRs) of the Rossmann-fold have been shown to catalyze this reaction. Here, we describe the characterization of Rv2074 from Mycobacterium tuberculosis, which belongs to a structurally and mechanistically distinct family of F420 H2 -dependent BVRs (F-BVRs) that are exclusively found in Actinobacteria. We have solved the crystal structure of Rv2074 bound to its cofactor, F420 , and used this alongside molecular dynamics simulations, site-directed mutagenesis and NMR spectroscopy to elucidate its catalytic mechanism. The production of bilirubin by Rv2074 could exploit the anti-oxidative properties of bilirubin and contribute to the range of immuno-evasive mechanisms that have evolved in M. tuberculosis to allow persistent infection. << Less