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
-
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
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
1,4-dihydroxy-6-naphthoate biosynthesis II
-
-
Biosynthesis of secondary metabolites
-
-
Ubiquinone and other terpenoid-quinone biosynthesis
-
-
1,4-dihydroxy-6-naphthoate biosynthesis
-
-
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
-
-
-
-
?
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
-
-
-
-
?
deaminated S-adenosyl-L-homocysteine + H2O
?
show the reaction diagram
-
33% activity compared to 5'-methylthioadenosine
-
-
?
decarboxylated S-adenosyl-L-homocysteine + H2O
?
show the reaction diagram
-
18% activity compared to 5'-methylthioadenosine
-
-
?
S-2-aza-adenosyl-L-homocysteine + H2O
?
show the reaction diagram
-
27% activity compared to 5'-methylthioadenosine
-
-
?
S-adenosyl-D-homocysteine + H2O
?
show the reaction diagram
-
26% activity compared to 5'-methylthioadenosine
-
-
?
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
?
-
-
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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-
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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
-
-
(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
-
-
(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
-
poor inhibitor
5'-Isobutylthioinosine
-
-
5'-methylthio-3-deaza-adenosine
-
poor inhibitor
5'-Methylthioformycin
-
powerful inhibitor
5'-methylthiotubercidin
-
powerful inhibitor
5'-n-butylthioinosine
-
-
adenine
-
poor inhibitor
methylthio-DADMe-immucillin-A
-
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
-
powerful inhibitor
-
S-N6-dimethyl-3-deaza-adenosyl-L-homocysteine
-
poor inhibitor
S-Tubercidinylhomocysteine
-
powerful inhibitor
sinefungin
-
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, 25C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.53
6-amino-6-deoxyfutalosine
Campylobacter jejuni
Q0PC20
pH 7, 25C
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
-
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 37C
0.000027
5'-Methylthioformycin
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
0.0041
5'-methylthiotubercidin
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
0.000928
S-8-aza-adenosyl-L-homocysteine
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
0.0000097
S-Formycinylhomocysteine
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
-
0.0019
S-Tubercidinylhomocysteine
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
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 37C
0.013
5'-isobutylthio-3-deaza-adenosine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
0.132
5'-Isobutylthioinosine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
0.079
5'-methylthio-3-deaza-adenosine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
0.00006
5'-Methylthioformycin
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
0.0077
5'-methylthiotubercidin
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
0.094
5'-n-butylthioinosine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
0.216
adenine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
0.0018
S-8-aza-adenosyl-L-homocysteine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
0.069
S-adenosyl-L-homocysteine sulfoxide
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
0.00002
S-Formycinylhomocysteine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
-
0.02
S-N6-dimethyl-3-deaza-adenosyl-L-homocysteine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
0.0032
S-Tubercidinylhomocysteine
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
0.024
sinefungin
Escherichia coli
-
in 50 mM potassium phosphate buffer, pH 7.0, at 37C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.38
-
using adenosine as substrate, at pH 6.0 and 22C
0.83
-
using 5'-chloroadenosine as substrate, at pH 6.0 and 22C
1.06
-
using 5'-iodoadenosine as substrate, at pH 6.0 and 22C
1.5
-
using 5'-butylthioadenosine as substrate, at pH 6.0 and 22C
1.98
-
using 5'-isobutylthioadenosine as substrate, at pH 6.0 and 22C
2.44
-
using 5'-phenylthioadenosine as substrate, at pH 6.0 and 22C
6.25
-
using 5'-methylthioadenosine as substrate, at pH 6.0 and 22C
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 18C
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 60C
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, 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