Information on EC 1.13.11.79 - 5,6-dimethylbenzimidazole synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.13.11.79
-
RECOMMENDED NAME
GeneOntology No.
5,6-dimethylbenzimidazole synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
FMNH2 + O2 = 5,6-dimethylbenzimidazole + D-erythrose 4-phosphate + other product(s)
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
5,6-dimethylbenzimidazole biosynthesis I (aerobic)
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adenosylcobalamin biosynthesis from cobyrinate a,c-diamide II
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Metabolic pathways
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Riboflavin metabolism
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vitamin B12 metabolism
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SYSTEMATIC NAME
IUBMB Comments
FMNH2 oxidoreductase (5,6-dimethylbenzimidazole forming)
The enzyme catalyses a complex oxygen-dependent conversion of reduced flavin mononucleotide to form 5,6-dimethylbenzimidazole, the lower ligand of vitamin B12. This conversion involves many sequential steps in two distinct stages, and an alloxan intermediate that acts as a proton donor, a proton acceptor, and a hydride acceptor [4]. The C-2 of 5,6-dimethylbenzimidazole is derived from C-1' of the ribityl group of FMNH2 and 2-H from the ribityl 1'-pro-S hydrogen. While D-erythrose 4-phosphate has been shown to be one of the byproducts, the nature of the other product(s) has not been verified yet.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
FMNH2 + NADH + H+ + O2
5,6-dimethylbenzimidazole + D-erythrose 4-phosphate + NAD+ + H2O
show the reaction diagram
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-
-
-
?
FMNH2 + NADH + H+ + O2 + alloxan
5,6-dimethylbenzimidazole + D-erythrose 4-phosphate + NAD+ + dialuric acid
show the reaction diagram
FMNH2 + NADH + H+ + O2 + H2O
5,6-dimethylbenzimidazole + D-erythrose 4-phosphate + NAD+ + ?
show the reaction diagram
-
-
-
?
FMNH2 + O2
5,6-dimethylbenzimidazole + ?
show the reaction diagram
-
FMNH2 reacts with oxygen to yield flavin hydroperoxide, which then undergoes a ring expansion with loss of a water molecule to produce intermediate A. This disintegrates further as a result of four hydrolysis reactions in which it is attacked by water molecules. The resulting diaminobenzene product undergoes two oxidation reactions, to form 5,6-dimethylbenzimidazole
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-
?
FMNH2 + O2
5,6-dimethylbenzimidazole + D-erythrose 4-phosphate + urea
show the reaction diagram
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
FMNH2 + NADH + H+ + O2 + alloxan
5,6-dimethylbenzimidazole + D-erythrose 4-phosphate + NAD+ + dialuric acid
show the reaction diagram
-
-
-
-
?
FMNH2 + O2
5,6-dimethylbenzimidazole + ?
show the reaction diagram
-
FMNH2 reacts with oxygen to yield flavin hydroperoxide, which then undergoes a ring expansion with loss of a water molecule to produce intermediate A. This disintegrates further as a result of four hydrolysis reactions in which it is attacked by water molecules. The resulting diaminobenzene product undergoes two oxidation reactions, to form 5,6-dimethylbenzimidazole
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-
?
FMNH2 + O2
5,6-dimethylbenzimidazole + D-erythrose 4-phosphate + urea
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.064
FMNH2
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pH 7.5, 22C
5.1
NADH
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pH 7.5, 22C
4.4
NADPH
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pH 7.5, 22C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.018
FMNH2
Sinorhizobium meliloti
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pH 7.5, 22C
0.002
NADH
Sinorhizobium meliloti
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pH 7.5, 22C
0.002
NADPH
Sinorhizobium meliloti
-
pH 7.5, 22C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.231
FMNH2
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pH 7.5, 22C
PDB
SCOP
CATH
ORGANISM
UNIPROT
Rhizobium meliloti (strain 1021)
Rhizobium meliloti (strain 1021)
Rhizobium meliloti (strain 1021)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
23900
2 * 23900, calculated
25000
-
x * 25000, SDS-PAGE
27300
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x * 27300, SDS-PAGE
47000
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
2 * 23900, calculated
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
metal affinity chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Salmonella enterica strain JE9385 and in Escherichia coli
Show AA Sequence (195 entries)
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