Information on EC 3.2.2.30 - aminodeoxyfutalosine nucleosidase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
3.2.2.30
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RECOMMENDED NAME
GeneOntology No.
aminodeoxyfutalosine nucleosidase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
6-amino-6-deoxyfutalosine + H2O = dehypoxanthine futalosine + adenine
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
1,4-dihydroxy-6-naphthoate biosynthesis II
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1,4-dihydroxy-6-naphthoate biosynthesis
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Ubiquinone and other terpenoid-quinone biosynthesis
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
6-amino-6-deoxyfutalosine ribohydrolase
The enzyme, found in several bacterial species, catalyses a step in a modified futalosine pathway for menaquinone biosynthesis. While the enzyme from some organisms also has the activity of EC 3.2.2.9, adenosylhomocysteine nucleosidase, the enzyme from Chlamydia trachomatis is specific for 6-amino-6-deoxyfutalosine [7].
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
5'-butylthioadenosine + H2O
?
show the reaction diagram
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-
-
-
?
5'-chloroadenosine + H2O
?
show the reaction diagram
-
-
-
-
?
5'-iodoadenosine + H2O
?
show the reaction diagram
-
-
-
-
?
5'-isobutylthioadenosine + H2O
?
show the reaction diagram
-
-
-
-
?
5'-methylthioadenosine + H2O
?
show the reaction diagram
-
-
-
-
?
5'-phenylthioadenosine + H2O
?
show the reaction diagram
-
-
-
-
?
5,5'-dithiobis-2-nitrobenzoic acid + H2O
?
show the reaction diagram
-
-
-
-
?
6-amino-6-deoxyfutalosine + H2O
adenine + dehypoxanthinyl futalosine
show the reaction diagram
6-amino-6-deoxyfutalosine + H2O
dehypoxanthine futalosine + adenine
show the reaction diagram
adenosine + H2O
?
show the reaction diagram
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-
-
-
?
deaminated S-adenosyl-L-homocysteine + H2O
?
show the reaction diagram
-
33% activity compared to 5'-methylthioadenosine
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-
?
decarboxylated S-adenosyl-L-homocysteine + H2O
?
show the reaction diagram
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18% activity compared to 5'-methylthioadenosine
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-
?
S-2-aza-adenosyl-L-homocysteine + H2O
?
show the reaction diagram
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27% activity compared to 5'-methylthioadenosine
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-
?
S-adenosyl-D-homocysteine + H2O
?
show the reaction diagram
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26% activity compared to 5'-methylthioadenosine
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-
?
additional information
?
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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
6-amino-6-deoxyfutalosine + H2O
adenine + dehypoxanthinyl futalosine
show the reaction diagram
6-amino-6-deoxyfutalosine + H2O
dehypoxanthine futalosine + adenine
show the reaction diagram
additional information
?
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-
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase is a multifunctional enzyme that catalyzes the hydrolysis of the N-ribosidic bond of at least four different adenosine-based metabolites: S-adenosyl-L-homocysteine, 5'-methylthioadenosine, 5'-deoxyadenosine, and 6-amino-6-deoxyfutalosine
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-methylthio-D-ribitol
(2R)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-(methylsulfanyl)propan-1-ol
(2R)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-[(hydroxymethyl)sulfanyl]propan-1-ol
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(2R,3R)-2-([[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl](methyl)amino]methyl)-4-(methylsulfanyl)butane-1,3-diol
(2R,3R)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-4-(methylsulfanyl)butane-1,3-diol
(2R,3S)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-4-(methylsulfanyl)butane-1,3-diol
(2R,3S)-4-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl](methyl)amino]-3-[(methylsulfanyl)methyl]butane-1,2-diol
(2S)-1-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-(methylsulfanyl)propan-2-ol
(2S)-2-[[(1S)-1-(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-2-hydroxyethyl]amino]-3-(methylsulfanyl)propan-1-ol
(2S)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-[(hydroxymethyl)sulfanyl]propan-1-ol
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(2S,3R)-1-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl](methyl)amino]-4-(methylsulfanyl)butane-2,3-diol
(2S,3R)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-4-(methylsulfanyl)butane-1,3-diol
(2S,3R)-N-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-3,4-dihydroxy-2-[(methylsulfanyl)methyl]butan-1-aminium trifluoroacetate
(2S,3S)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-4-(methylsulfanyl)butane-1,3-diol
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]3-hydroxy-4-methylthiomethylpyrrolidine
2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-2-[(methylsulfanyl)methyl]propane-1,3-diol
2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-(methylsulfanyl)propan-1-ol
5'-Chloroformycin
-
powerful inhibitor
5'-isobutylthio-3-deaza-adenosine
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poor inhibitor
5'-Isobutylthioinosine
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-
5'-methylthio-3-deaza-adenosine
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poor inhibitor
5'-Methylthioformycin
-
powerful inhibitor
5'-methylthiotubercidin
-
powerful inhibitor
5'-n-butylthioinosine
-
-
adenine
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poor inhibitor
methylthio-DADMe-immucillin-A
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i.e. (3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(methylsulfanyl)methyl]pyrrolidin-3-ol
S-8-aza-adenosyl-L-homocysteine
-
powerful inhibitor
S-adenosyl-L-homocysteine sulfoxide
-
poor inhibitor
S-Formycinylhomocysteine
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powerful inhibitor
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S-N6-dimethyl-3-deaza-adenosyl-L-homocysteine
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poor inhibitor
S-Tubercidinylhomocysteine
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powerful inhibitor
sinefungin
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poor inhibitor
Tris
weak inhibitor, about 20% residual activity at 250 mM
additional information
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not inhibited by 5'-methylthioinosine, S-inosyl-L-homocysteine, S-guanosyl-L-homocysteine, S-N6-methyl-3-deaza-adenosyl-L-homocysteine, S-adenosyl-L-homocysteine dialdehyde, acyclic adenosyl-L-homocysteine, S-cytidylhomocysteine, hypoxanthine, guanine, and AMP
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.001
6-amino-6-deoxyfutalosine
pH 7, 25°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.53
6-amino-6-deoxyfutalosine
pH 7, 25°C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00000008 - 0.00000036
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-methylthio-D-ribitol
0.0000008 - 0.0000017
(2R)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-(methylsulfanyl)propan-1-ol
0.00000023
(2R)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-[(hydroxymethyl)sulfanyl]propan-1-ol
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pH and temperature not specified in the publication
0.000132 - 0.000401
(2R,3R)-2-([[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl](methyl)amino]methyl)-4-(methylsulfanyl)butane-1,3-diol
0.00001
(2R,3R)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-4-(methylsulfanyl)butane-1,3-diol
0.0000008 - 0.0000009
(2R,3S)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-4-(methylsulfanyl)butane-1,3-diol
0.000061 - 0.0023
(2R,3S)-4-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl](methyl)amino]-3-[(methylsulfanyl)methyl]butane-1,2-diol
0.000036 - 0.00004
(2S)-1-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-(methylsulfanyl)propan-2-ol
0.000047 - 0.00172
(2S)-2-[[(1S)-1-(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-2-hydroxyethyl]amino]-3-(methylsulfanyl)propan-1-ol
0.0000011
(2S)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-[(hydroxymethyl)sulfanyl]propan-1-ol
-
pH and temperature not specified in the publication
0.000085 - 0.000202
(2S,3R)-1-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl](methyl)amino]-4-(methylsulfanyl)butane-2,3-diol
0.0000039 - 0.000006
(2S,3R)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-4-(methylsulfanyl)butane-1,3-diol
0.000005 - 0.000009
(2S,3R)-N-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-3,4-dihydroxy-2-[(methylsulfanyl)methyl]butan-1-aminium trifluoroacetate
0.0000018 - 0.0000021
(2S,3S)-2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-4-(methylsulfanyl)butane-1,3-diol
0.000000002 - 0.00000014
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]3-hydroxy-4-methylthiomethylpyrrolidine
0.000004 - 0.0000058
2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-2-[(methylsulfanyl)methyl]propane-1,3-diol
0.00000036 - 0.0000012
2-[[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-(methylsulfanyl)propan-1-ol
0.000322
5'-Chloroformycin
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
0.000027
5'-Methylthioformycin
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
0.0041
5'-methylthiotubercidin
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
0.000928
S-8-aza-adenosyl-L-homocysteine
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
0.0000097
S-Formycinylhomocysteine
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
-
0.0019
S-Tubercidinylhomocysteine
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0004
5'-Chloroformycin
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
0.013
5'-isobutylthio-3-deaza-adenosine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
0.132
5'-Isobutylthioinosine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
0.079
5'-methylthio-3-deaza-adenosine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
0.00006
5'-Methylthioformycin
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
0.0077
5'-methylthiotubercidin
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
0.094
5'-n-butylthioinosine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
0.216
adenine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
0.0018
S-8-aza-adenosyl-L-homocysteine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
0.069
S-adenosyl-L-homocysteine sulfoxide
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
0.00002
S-Formycinylhomocysteine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
-
0.02
S-N6-dimethyl-3-deaza-adenosyl-L-homocysteine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
0.0032
S-Tubercidinylhomocysteine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
0.024
sinefungin
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37°C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.38
-
using adenosine as substrate, at pH 6.0 and 22°C
0.83
-
using 5'-chloroadenosine as substrate, at pH 6.0 and 22°C
1.06
-
using 5'-iodoadenosine as substrate, at pH 6.0 and 22°C
1.5
-
using 5'-butylthioadenosine as substrate, at pH 6.0 and 22°C
1.98
-
using 5'-isobutylthioadenosine as substrate, at pH 6.0 and 22°C
2.44
-
using 5'-phenylthioadenosine as substrate, at pH 6.0 and 22°C
6.25
-
using 5'-methylthioadenosine as substrate, at pH 6.0 and 22°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
PDB
SCOP
CATH
ORGANISM
UNIPROT
Helicobacter pylori (strain ATCC 700392 / 26695)
Helicobacter pylori (strain ATCC 700392 / 26695)
Helicobacter pylori (strain ATCC 700392 / 26695)
Helicobacter pylori (strain ATCC 700392 / 26695)
Helicobacter pylori (strain J99 / ATCC 700824)
Helicobacter pylori (strain J99 / ATCC 700824)
Helicobacter pylori (strain J99 / ATCC 700824)
Helicobacter pylori (strain J99 / ATCC 700824)
Helicobacter pylori (strain J99 / ATCC 700824)
Helicobacter pylori (strain J99 / ATCC 700824)
Helicobacter pylori (strain J99 / ATCC 700824)
Helicobacter pylori (strain J99 / ATCC 700824)
Helicobacter pylori (strain J99 / ATCC 700824)
Helicobacter pylori (strain J99 / ATCC 700824)
Helicobacter pylori (strain J99 / ATCC 700824)
Helicobacter pylori (strain J99 / ATCC 700824)
Helicobacter pylori (strain J99 / ATCC 700824)
Helicobacter pylori (strain J99 / ATCC 700824)
Helicobacter pylori (strain J99 / ATCC 700824)
Helicobacter pylori (strain J99 / ATCC 700824)
Helicobacter pylori (strain J99 / ATCC 700824)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
27462
-
x * 27462, isoform MATN2, calculated from amino acid sequence
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
x * 27462, isoform MATN2, calculated from amino acid sequence
homodimer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
enzyme only or in complex with formycin A or adenine, hanging drop vapor diffusion method, using 0.1 M Tris pH 8.5 and 16% (w/v) polyethyleneglycol 8000, at 18°C
hanging drop vapor diffusion method, mutants E14Q (0.1 M HEPES pH 7.5, 25% (w/v) PEG 3350, 0.2 M NaCl), D199N (0.1 M bis-Tris pH 5.5, 25% (w/v) PEG 3350, 0.2 M MgCl2-6H2O) and D199A (0.1 M bis-tris pH 6.5, 25% (w/v) PEG 3350, 0.2 M Li2SO4-H2O); wild type and mutant enzymes E14Q, D199N, and D199A, sitting drop vapor diffusion method, using 4.0 M NaH2PO4/K2HPO4 pH 7.0 (wild type), 0.1 M HEPES pH 7.5, 25% PEG 3350, 0.2 M NaCl (E14Q), 0.1 M bis-Tris pH 5.5, 25% (w/v) PEG 3350, 0.2 M MgCl2-6H2O (D199N), and 0.1 M bis-Tris pH 6.5, 25% (w/v) PEG 3350, 0.2 M Li2SO4-H2O (D199A)
hanging drop vapor diffusion method. Inactive D198N mutant bound to 5'-methylthioadenosine using 0.2 M magnesium chloride, 0.1 M HEPES (pH 7.5), and 25% (w/v) PEG 3350
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60
-
the enzyme is rapidly inactivated after exposure for 15 min at 60°C
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 50 mM potassium phosphate buffer (pH 7.0), at least 2 months, no significant loss of activity
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate precipitation, DEAE-Sephadex gel filtration, hydroxyapatite column chromatography, S-formycinylhomocysteine-Sepharose column chromatography, and Sephacryl S-200 gel filtration
-
HisTrap column chromatography and Superdex 200 gel filtration
-
HisTrap column chromatography; HisTrap column chromatography and Superdex 75 gel filtration
Ni-NTA affinity column chromatography and gel filtration
Ni-NTA agarose column chromatography
-
Ni-NTA column chromatography and Superdex 200 gel filtration
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21 Codon+ cells
-
expressed in Escherichia coli BL21(DE3) cells
expressed in Escherichia coli BL21(DE3) Rosetta cells
-
expression in Escherichia coli as a His-tagged protein
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D198N
-
inactive
D199A
active-site mutant; inactive
D199N
active-site mutant; the mutant shows residual activity
E14Q
active-site mutant; the mutant shows residual activity
D199A
-
inactive
-
E173Q
-
inactive
F104C/C186S
-
the mutations give an enzyme with steady-state kinetic properties similar to the native enzyme