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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
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
N5-formyl-5,6,7,8-tetrahydromethanopterin
formyl-tetrahydromethanopterin
methenyl-tetrahydromethanopterin + H2O
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
?
-
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
?
-
-
-
-
?
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
?
-
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
?
-
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
-
-
-
?
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
-
-
-
?
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
-
-
-
?
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
?
formyl-tetrahydromethanopterin
methenyl-tetrahydromethanopterin + H2O
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
?
-
-
-
-
?
5,10-methenyl-5,6,7,8-tetrahydromethanopterin + H2O
?
-
-
-
-
?
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
?
-
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
?
-
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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0.025 - 0.077
5,10-methenyl-5,6,7,8-tetrahydromethanopterin
0.03 - 0.22
formyl-tetrahydromethanopterin
0.03 - 2
N5,N10-methenyl-5,6,7,8-tetrahydromethanopterin
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
0.06
5,10-methenyl-5,6,7,8-tetrahydromethanopterin
pH 7.6, 10°C
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
formyl-tetrahydromethanopterin
-
-
0.04
formyl-tetrahydromethanopterin
-
pH 8.0, 65°C
0.22
formyl-tetrahydromethanopterin
-
-
0.03
N5,N10-methenyl-5,6,7,8-tetrahydromethanopterin
-
-
0.03
N5,N10-methenyl-5,6,7,8-tetrahydromethanopterin
-
recombinant enzyme
0.04
N5,N10-methenyl-5,6,7,8-tetrahydromethanopterin
-
-
0.1
N5,N10-methenyl-5,6,7,8-tetrahydromethanopterin
-
1 M K2HPO4
0.14
N5,N10-methenyl-5,6,7,8-tetrahydromethanopterin
-
0.6 M K2HPO4
0.2
N5,N10-methenyl-5,6,7,8-tetrahydromethanopterin
-
0.3 M K2HPO4
0.22
N5,N10-methenyl-5,6,7,8-tetrahydromethanopterin
-
-
0.57
N5,N10-methenyl-5,6,7,8-tetrahydromethanopterin
-
-
2
N5,N10-methenyl-5,6,7,8-tetrahydromethanopterin
-
-
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Pomper, B.K.; Vorholt, J.A.; Chistoserdova, L.; Lidstrom, M.E.; Thauer, R.K.
A methenyl tetrahydromethanopterin cyclohydrolase and a methenyl tetrahydrofolate cyclohydrolase in Methylobacterium extorquens AM1
Eur. J. Biochem.
261
475-480
1999
Methylorubrum extorquens, Methylorubrum extorquens ATCC 14718 / DSM 1338 / JCM 2805 / NCIMB 9133 / AM1
brenda
Donnelly, M.I.; Escalante-Semerena, J.C.; Rinehart, K.L.; Wolfe, R.S.
Methenyl-tetrahydromethanopterin cyclohydrolase in cell extracts of Methanobacterium
Arch. Biochem. Biophys.
242
430-439
1985
Methanothermobacter thermautotrophicus
brenda
Dimarco, A.A.; Donnelly, M.I.; Wolfe, R.S.
Purification and properties of the 5,10-methenyltetrahydromethanopterin cyclohydrolase from Methanobacterium thermoautotrophicum
J. Bacteriol.
168
1372-1377
1986
Methanothermobacter thermautotrophicus
brenda
te Boemmelstroet, B.W.; Hensgens, C.M.H.; Geerts, W.J.; Keltjens, J.T.; van der Drift, C.; Vogels, G.D.
Purification and properties of 5,10-methenyltetrahydromethanopterin cyclohydrolase from Methanosarcina barkeri
J. Bacteriol.
172
564-571
1990
Methanosarcina barkeri
brenda
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
brenda
Breitung, J.; Schmitz, R.A.; Stetter, K.O.; Thauer, R.K.
N5,N10-Methenyltetrahydromethanopterin cyclohydrolase from the extreme thermophile Methanopyrus kandleri: increase of the catalytic efficiency (kcat/KM) and thermostability in the presence of salts
Arch. Microbiol.
156
517-524
1991
Methanopyrus kandleri
-
brenda
Grabarse, W.; Vaupel, M.; Vorholt, J.A.; Shima, S.; Thauer, R.K.; Wittershagen, A.; Bourenkov, G.; Bartunik, H.D.; Ermler, U.
The crystal structure of methenyltetrahydromethanopterin cyclohydrolase from the hyperthermophilic archaeon Methanopyrus kandleri
Structure Fold. Des.
7
1257-1268
1999
Methanopyrus kandleri
brenda
Vaupel, M.; Vorholt, J.A.; Thauer, R.K.
Overproduction and one-step purification of the N5,N10-methenyltetrahydromethanopterin cyclohydrolase (Mch) from the hyperthermophilic Methanopyrus kandleri
Extremophiles
2
15-22
1998
Methanosarcina barkeri, Methanothermobacter thermautotrophicus, Methanocaldococcus jannaschii, Methanopyrus kandleri
brenda
Vorholt, J.A.; Christoserdova, L.; Stolyar, S.M.; Thauer, R.K.; Lidstrom, M.E.
Distribution of tetrahydromethanopterin-dependent enzymes in methylotrophic bacteria and phylogeny of methenyl tetrahydromethanopterin cyclohydrolase
J. Bacteriol.
181
5750-5757
1999
Xanthobacter autotrophicus, Hyphomicrobium methylovorum, Methylobacillus flagellatus, Methylorubrum extorquens, Methylobacterium organophilum, Methylococcus thermophilus, Methylomicrobium album, Methylophilus methylotrophus, Methylosinus trichosporium, Xanthobacter flavus, Methylomonas rubra (Q9RPW2), Methylococcus capsulatus (Q9RPW8), Methylorubrum extorquens ATCC 14718 / DSM 1338 / JCM 2805 / NCIMB 9133 / AM1, Methylococcus capsulatus Bath (Q9RPW8), Methylophilus methylotrophus AS1, Methylomicrobium album BG8, Methylomonas rubra 15sh (Q9RPW2), Methylococcus thermophilus IIIp, Xanthobacter flavus H4-14
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Archaeoglobus profundus, Archaeoglobus lithotrophicus, Archaeoglobus lithotrophicus TF-2, Archaeoglobus profundus DSM 5631
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Ferroglobus placidus, Ferroglobus placidus DSM 10642
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Archaeoglobus fulgidus (O28344)
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Shima, S.; Herault, D.A.; Berkessel, A.; Thauer, R.K.
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Methanopyrus kandleri
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Kojima, H.; Moll, J.; Kahnt, J.; Fukui, M.; Shima, S.
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Methanobrevibacter ruminantium (D3E4S5), Methanobrevibacter ruminantium, Methanobrevibacter ruminantium DSM 1093 (D3E4S5)
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Shima, S.; Herault, D.; Berkessel, A.; Thauer, R.
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Methanopyrus kandleri
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