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Information on EC 3.5.4.27 - methenyltetrahydromethanopterin cyclohydrolase
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EC Tree
3.5.4.27 methenyltetrahydromethanopterin cyclohydrolaseIUBMB Comments
Methanopterin is a pterin analogue. The enzyme is involved in the formation of methane from CO2 in Methanobacterium thermoautotrophicum.
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Word Map
- 3.5.4.27
-
methanobacterium
- thermoautotrophicum
- archaea
- methane
-
formyltransferase
-
methanogenic
- formylmethanofuran
-
methanogenesis
- methylenetetrahydromethanopterin
-
formylmethanofuran:tetrahydromethanopterin
- dioxide
- kandleri
-
methanosarcina
-
methanopyrus
-
methanotrophic
-
donnelly
- marburg
-
wolfe
-
lyotropic
-
monoxide
-
hyperthermophilic
- barkeri
- archaeoglobus
-
consortia
- tetrahydrofolate
The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
Reaction Schemes
Synonyms
n5,n10-methenyltetrahydromethanopterin cyclohydrolase, methenyltetrahydromethanopterin cyclohydrolase, 5,10-methenyltetrahydromethanopterin cyclohydrolase, methenyl-h4mpt cyclohydrolase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
5,10-methenyltetrahydromethanopterin cyclohydrolase
-
-
-
-
hydrolase, methenyltetrahydromethanopterin cyclo-
-
-
-
-
Mch
methenyl-H4MPT cyclohydrolase
N5,N10-methenyltetrahydromethanopterin cyclohydrolase
methenyl-H4MPT cyclohydrolase
-
-
-
-
N5,N10-methenyltetrahydromethanopterin cyclohydrolase
-
-
-
-
N5,N10-methenyltetrahydromethanopterin cyclohydrolase
-
-
N5,N10-methenyltetrahydromethanopterin cyclohydrolase
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O = 5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis of cyclic amidines
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
5,10-methenyltetrahydromethanopterin 10-hydrolase (decyclizing)
Methanopterin is a pterin analogue. The enzyme is involved in the formation of methane from CO2 in Methanobacterium thermoautotrophicum.
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CAS REGISTRY NUMBER
COMMENTARY
99533-50-3
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
5-formyl-5,6,7,8-tetrahydromethanopterin
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
5-formyl-5,6,7,8-tetrahydromethanopterin
the active site is primarily built up by the segment 93:95, Arg183 and Glu186 that either interact with the catalytic water attacking 5,10-methenyl-5,6,7,8-tetrahydromethanopterin or with the formyl oxygen of 5-formyl-5,6,7,8-tetrahydromethanopterin. The catalytic function of the strictly conserved Arg183 and Glu186 is substantiated by the low enzymatic activities of the E186A, E186D, E186N, E186Q, R183A, R183Q, R183E, R183K, and R183E-E186Q variants. Glu186 most likely acts as a general base. Arg183 decisively influences the pKa value of Glu186 and the proposed catalytic water mainly by its positive charge. In addition, Glu186 appears to be also responsible for product specificity by donating a proton to the directly neighbored N10 tertiary amine of H4MPT. Thus, N10 becomes a better leaving group than N5 which implies the generation of 5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
5-formyl-5,6,7,8-tetrahydromethanopterin
enzyme residue Lys77 binds to the phosphate moiety of substrate moiety H4MPT
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
5-formyl-5,6,7,8-tetrahydromethanopterin
enzyme residue Lys77 binds to the phosphate moiety of substrate moiety H4MPT
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
r
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
?
-
in acetate-grown cells the cyclohydrolase level is lowered 2 to 3fold, in cultures growing on acetate supplemented with methanol or H2CO cyclohydrolase activity level increases 3 to 4fold
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
?
Methanosarcina barkeri Fusaro / DSM 804
-
in acetate-grown cells the cyclohydrolase level is lowered 2 to 3fold, in cultures growing on acetate supplemented with methanol or H2CO cyclohydrolase activity level increases 3 to 4fold
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
?
-
enzyme is involved in methanogenesis from CO2 and H2, which represents the energy metabolism
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
?
-
enzyme is involved in the formation of methane from CO2 in Methanobacterium thermoautotrophicum
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
?
-
the enzyme might have a catabolic function in the C1-unit metabolism
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
?
Methylorubrum extorquens ATCC 14718 / DSM 1338 / JCM 2805 / NCIMB 9133 / AM1
-
the enzyme might have a catabolic function in the C1-unit metabolism
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
r
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
r
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
Methanosarcina barkeri Fusaro / DSM 804
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
N10-formyl-5,6,7,8-tetrahydromethanopterin is the nonenzymatic reaction product
r
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
the methenyl derivative is favored over 5-formyltetrahydromethanopterin
-
r
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
Methylorubrum extorquens ATCC 14718 / DSM 1338 / JCM 2805 / NCIMB 9133 / AM1
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
Methylorubrum extorquens ATCC 14718 / DSM 1338 / JCM 2805 / NCIMB 9133 / AM1
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
formyl-tetrahydromethanopterin
methenyl-tetrahydromethanopterin + H2O
-
-
-
-
r
formyl-tetrahydromethanopterin
methenyl-tetrahydromethanopterin + H2O
-
-
-
-
r
formyl-tetrahydromethanopterin
methenyl-tetrahydromethanopterin + H2O
-
substrate isolated and purified from Methanobacterium thermoautotrophicum, overview
-
-
r
formyl-tetrahydromethanopterin
methenyl-tetrahydromethanopterin + H2O
-
-
-
-
r
formyl-tetrahydromethanopterin
methenyl-tetrahydromethanopterin + H2O
-
-
-
-
r
formyl-tetrahydromethanopterin
methenyl-tetrahydromethanopterin + H2O
-
-
-
-
r
formyl-tetrahydromethanopterin
methenyl-tetrahydromethanopterin + H2O
-
-
-
-
r
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
5-formyl-5,6,7,8-tetrahydromethanopterin
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
5-formyl-5,6,7,8-tetrahydromethanopterin
-
-
-
r
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
?
-
in acetate-grown cells the cyclohydrolase level is lowered 2 to 3fold, in cultures growing on acetate supplemented with methanol or H2CO cyclohydrolase activity level increases 3 to 4fold
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
?
Methanosarcina barkeri Fusaro / DSM 804
-
in acetate-grown cells the cyclohydrolase level is lowered 2 to 3fold, in cultures growing on acetate supplemented with methanol or H2CO cyclohydrolase activity level increases 3 to 4fold
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
?
-
enzyme is involved in methanogenesis from CO2 and H2, which represents the energy metabolism
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
?
-
enzyme is involved in the formation of methane from CO2 in Methanobacterium thermoautotrophicum
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
?
-
the enzyme might have a catabolic function in the C1-unit metabolism
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
?
Methylorubrum extorquens ATCC 14718 / DSM 1338 / JCM 2805 / NCIMB 9133 / AM1
-
the enzyme might have a catabolic function in the C1-unit metabolism
-
-
?
formyl-tetrahydromethanopterin
methenyl-tetrahydromethanopterin + H2O
-
-
-
-
r
formyl-tetrahydromethanopterin
methenyl-tetrahydromethanopterin + H2O
-
-
-
-
r
formyl-tetrahydromethanopterin
methenyl-tetrahydromethanopterin + H2O
-
-
-
-
r
formyl-tetrahydromethanopterin
methenyl-tetrahydromethanopterin + H2O
-
-
-
-
r
formyl-tetrahydromethanopterin
methenyl-tetrahydromethanopterin + H2O
-
-
-
-
r
formyl-tetrahydromethanopterin
methenyl-tetrahydromethanopterin + H2O
-
-
-
-
r
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
K+
activity in cell extract is dependent on the presence of high concentrations of potassium phosphate. The activity in 1.0 M potassium phosphate buffer pH 7.6 is eightfold higher than that in 0.12 M potassium phosphate buffer pH 7.6
K2HPO4
K2SO4
KCl
Mg2+
Na2HPO4
-
maximal activation by 1.5 M K2HPO4, 1 M Na2HPO4 or 1 M Na2SO4
Na2SO4
NaCl
additional information
K2HPO4
-
maximal activation by 1.5 M K2HPO4, 1 M Na2HPO4, or 1 M Na2SO4
NaCl
-
presence of salts required, activity in absence of salts is only 15% of that in the presence of salts
additional information
-
lyotrophic salts at high concentrations above 1 M are required for enzyme activity, but not for stability, 200fold activation
additional information
-
lyotrophic salts at high concentrations above 1 M are required for enzyme activity, but not for stability, 4fold activation
additional information
-
lyotrophic salts at high concentrations above 1 M are required for enzyme activity, but not for stability, 65fold activation
additional information
-
lyotrophic salts at high concentrations above 1 M are required for enzyme activity, but not for stability, 2fold activation
additional information
-
lyotrophic salts at high concentrations above 1 M are required for enzyme activity, but not for stability, 7fold activation
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2,3-diphosphoglycerate
-
the activity increases with increasing 2,3-diphosphoglycerate concentrations from 30 U/mg up to a specific activity of 7,500 U/mg. The maximal activity is reached at a 2,3-diphosphoglycerate concentration of 0.75 M. At higher concentrations, the activity decreases
cyclic 2,3-bisphosphoglycerate
-
optimally active at 0.75 M, about 7500 U/mg
-
2,3-bisphosphoglycerate
-
the potassium salts of 2,3-bisphosphoglycerate stimulates cyclohydrolase activity
phosphate
-
the potassium salts of phosphateglycerate stimulates cyclohydrolase activity
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
-
effect of salts on Km
-
0.025
5,10-methenyl-5,6,7,8-tetrahydromethanopterin
pH 7.6, 65°C, mutant enzyme R183E
0.026
5,10-methenyl-5,6,7,8-tetrahydromethanopterin
pH 7.6, 65°C, mutant enzyme E186A
0.043
5,10-methenyl-5,6,7,8-tetrahydromethanopterin
pH 7.6, 65°C, mutant enzyme R183A
0.043
5,10-methenyl-5,6,7,8-tetrahydromethanopterin
pH 7.6, 65°C, mutant enzyme R183K
0.043
5,10-methenyl-5,6,7,8-tetrahydromethanopterin
pH 7.6, 65°C, mutant enzyme R183Q
0.047
5,10-methenyl-5,6,7,8-tetrahydromethanopterin
pH 7.6, 65°C, mutant enzyme K94V
0.05
5,10-methenyl-5,6,7,8-tetrahydromethanopterin
pH 7.6, 65°C, mutant enzyme E186N
0.055
5,10-methenyl-5,6,7,8-tetrahydromethanopterin
pH 7.6, 65°C, wild-type enzyme
0.062
5,10-methenyl-5,6,7,8-tetrahydromethanopterin
pH 7.6, 65°C, mutant enzyme E186D
0.077
5,10-methenyl-5,6,7,8-tetrahydromethanopterin
pH 7.6, 65°C, mutant enzyme K94E
0.03
N5,N10-methenyl-5,6,7,8-tetrahydromethanopterin
-
recombinant enzyme
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.5
7.6
8.5
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
50
65
85
additional information
additional information
-
optimal growth temperature of the organism is 85°C
additional information
-
optimal growth temperature of the organism is 98°C
additional information
-
optimal growth temperature of the organism is 37°C
additional information
-
optimal growth temperature of the organism is 65°C
additional information
-
optimal growth temperature of the organism is 83°C
additional information
-
optimal growth temperature of the organism is 30°C
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30 - 70
30°C: about 75% of maximal activity, 70°C: about 55% of maximal activity
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4.3
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
DSM7471, originally isolated from the solar saltern of Figueria da Foz, Portugal
UniProt
brenda
DSM7471, originally isolated from the solar saltern of Figueria da Foz, Portugal
UniProt
brenda