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Information on EC 3.5.4.27 - methenyltetrahydromethanopterin cyclohydrolase and Organism(s) Archaeoglobus fulgidus and UniProt Accession O28344
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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
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methanobacterium
- thermoautotrophicum
- archaea
- methane
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formyltransferase
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methanogenic
- formylmethanofuran
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methanogenesis
- methylenetetrahydromethanopterin
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formylmethanofuran:tetrahydromethanopterin
- dioxide
- kandleri
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methanosarcina
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methanopyrus
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methanotrophic
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donnelly
- marburg
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wolfe
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lyotropic
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monoxide
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hyperthermophilic
- barkeri
- archaeoglobus
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consortia
- tetrahydrofolate
The taxonomic range for the selected organisms is: Archaeoglobus fulgidus
The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
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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topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
5,10-methenyltetrahydromethanopterin cyclohydrolase
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hydrolase, methenyltetrahydromethanopterin cyclo-
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methenyl-H4MPT cyclohydrolase
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N5,N10-methenyltetrahydromethanopterin cyclohydrolase
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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.
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
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-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
5-formyl-5,6,7,8-tetrahydromethanopterin
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?
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
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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
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?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
the enzyme catalyzes a reaction in the one-carbon energy metabolism of methanogenic, methanotrophic, and sulfate-reducing archaea and of methylotrophic bacteria
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor diffusion method in an anaerobic tent with an atmosphere of 95% N2/5% H2 under low-intensity red light. X-ray structures of the substrate-free E186Q mutant enzyme, the enzyme:5,10-methenyl-5,6,7,8-tetrahydromethanopterin complex, and the E186Q mutant enzyme:5-formyl-5,6,7,8-tetrahydromethanopterin complex
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
E186A
Vmax is 0.035% of wild-type activity, Km for 5,10-methenyl-5,6,7,8-tetrahydromethanopterin is 2.1fold lower compared to wild-type value
E186D
Vmax is 0.56% of wild-type activity, Km for 5,10-methenyl-5,6,7,8-tetrahydromethanopterin is 1.1fold higher compared to wild-type value
E186N
Vmax is 0.1% of wild-type activity, Km for 5,10-methenyl-5,6,7,8-tetrahydromethanopterin is 1.1fold lower compared to wild-type value
K94E
Vmax is 86% of wild-type activity, Km for 5,10-methenyl-5,6,7,8-tetrahydromethanopterin is 1.4fold lower compared to wild-type value
K94V
Vmax is 41% of wild-type activity, Km for 5,10-methenyl-5,6,7,8-tetrahydromethanopterin is 1.2fold lower compared to wild-type value
R183a
Vmax is 0.07% of wild-type activity, Km for 5,10-methenyl-5,6,7,8-tetrahydromethanopterin is 1.3fold lower compared to wild-type value
R183E
Vmax is 0.01% of wild-type activity, Km for 5,10-methenyl-5,6,7,8-tetrahydromethanopterin is 2.2fold lower compared to wild-type value
R183K
Vmax is 15% of wild-type activity, Km for 5,10-methenyl-5,6,7,8-tetrahydromethanopterin is 1.3fold lower compared to wild-type value
R183Q
Vmax is 0.05% of wild-type activity, Km for 5,10-methenyl-5,6,7,8-tetrahydromethanopterin is 1.3fold lower compared to wild-type value
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
90
90
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more than 80% loss of activity after 10 min without stabilizer, completely stable for more than 50 min with addition of 1.0 M K2HPO4
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Klein, A.R.; Breitung, J.; Linder, D.; Stetter, K.O.; Thauer, R.K.
N5,N10-Methenyltetrahydromethanopterin cyclohydrolase from the extremely thermophilic sulfate reducing Archaeoglobus fulgidus: comparison of its properties with those of the cyclohydrolase from the extremely thermophilic Methanopyrus kandleri
Arch. Microbiol.
159
213-219
1993
Archaeoglobus fulgidus, Methanopyrus kandleri
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