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EC Tree
IUBMB Comments This enzyme, found in bacteria and plants, acts on three different substrates. It is involved in the S-adenosyl-L-methionine (SAM, AdoMet) cycle, which recycles S-adenosyl-L-homocysteine back to SAM, and in salvage pathways for 5'-deoxyadenosine and S-methyl-5'-thioadenosine, which are produced from SAM during the action of many enzymes. cf. the plant enzyme EC 3.2.2.16, methylthioadenosine nucleosidase.
The taxonomic range for the selected organisms is: Helicobacter pylori The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Reaction Schemes
+
=
5-(methylsulfanyl)-D-ribose
+
Synonyms
nucleosidase, pfs-2, mta/adohcy nucleosidase, rv0091, s-adenosylhomocysteine nucleosidase, 5'-methylthioadenosine/s-adenosylhomocysteine, mtan-1, 5'-methylthioadenosine nucleosidases, adenosylhomocysteine nucleosidase, adohcy/mesado nucleosidase,
more
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5-methylthioadenosine/S-adenosylhomocysteine nucleosidase
-
5'-methyladenosine nucleosidase
-
-
-
-
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase
-
-
adoHcy/MTA nucleosidase
-
-
-
-
MTA/SAH nucleosidase
-
-
-
-
S-adenosylhomocysteine nucleosidase
-
-
-
-
S-adenosylhomocysteine/5'-methylthioadenosine nucleosidase
-
-
-
-
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hydrolysis of N-glycosyl bond
-
-
-
-
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S-adenosyl-L-homocysteine homocysteinylribohydrolase
This enzyme, found in bacteria and plants, acts on three different substrates. It is involved in the S-adenosyl-L-methionine (SAM, AdoMet) cycle, which recycles S-adenosyl-L-homocysteine back to SAM, and in salvage pathways for 5'-deoxyadenosine and S-methyl-5'-thioadenosine, which are produced from SAM during the action of many enzymes. cf. the plant enzyme EC 3.2.2.16, methylthioadenosine nucleosidase.
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5'-deoxyadenosine + H2O
5-deoxy-D-ribose + adenine
-
-
-
?
5'-methylthioadenosine + H2O
5-methylthio-D-ribose + adenine
-
-
-
?
S-adenosyl-L-homocysteine + H2O
S-(5-deoxy-D-ribos-5-yl)-L-homocysteine + adenine
-
-
-
ir
S-adenosyl-L-homocysteine + H2O
S-(5-deoxy-D-ribos-5-yl)-L-homocysteine + adenine
S-adenosyl-L-homocysteine + H2O
S-(5-deoxy-D-ribos-5-yl)-L-homocysteine + adenine
-
-
-
?
S-adenosyl-L-homocysteine + H2O
S-(5-deoxy-D-ribos-5-yl)-L-homocysteine + adenine
-
-
-
-
?
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S-adenosyl-L-homocysteine + H2O
S-(5-deoxy-D-ribos-5-yl)-L-homocysteine + adenine
S-adenosyl-L-homocysteine + H2O
S-(5-deoxy-D-ribos-5-yl)-L-homocysteine + adenine
-
-
-
?
S-adenosyl-L-homocysteine + H2O
S-(5-deoxy-D-ribos-5-yl)-L-homocysteine + adenine
-
-
-
-
?
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(4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(ethynylsulfanyl)methyl]pyrrolidin-3-ol
transition-state analogue, shows significant overlap in specificity with human 5'-methylthioadenosine phosphorylase MTAP
(4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[[(pent-4-yn-1-yl)sulfanyl]methyl]pyrrolidin-3-ol
transition-state analogue, best binding inhibitor tested, shows significant overlap in specificity with human 5'-methylthioadenosine phosphorylase MTAP
Tris
weak inhibitor, about 20% residual activity at 250 mM
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0.0449
5'-methylthioadenosine
at 37°C in 100 mM HEPES, 50 mM KCl, pH 7.5
0.01 - 0.019
S-adenosyl-L-homocysteine
0.01
S-adenosyl-L-homocysteine
-
wild type enzyme, in 100 mM HEPES and 50 mM KCl buffer (pH 7.2), at 37°C
0.014
S-adenosyl-L-homocysteine
-
mutant enzyme H109A, in 100 mM HEPES and 50 mM KCl buffer (pH 7.2), at 37°C
0.019
S-adenosyl-L-homocysteine
-
mutant enzyme F107A, in 100 mM HEPES and 50 mM KCl buffer (pH 7.2), at 37°C
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4.92
5'-methylthioadenosine
at 37°C in 100 mM HEPES, 50 mM KCl, pH 7.5
0.44 - 1.8
S-adenosyl-L-homocysteine
0.44
S-adenosyl-L-homocysteine
-
mutant enzyme F107A, in 100 mM HEPES and 50 mM KCl buffer (pH 7.2), at 37°C
0.74
S-adenosyl-L-homocysteine
-
mutant enzyme H109A, in 100 mM HEPES and 50 mM KCl buffer (pH 7.2), at 37°C
1.8
S-adenosyl-L-homocysteine
-
wild type enzyme, in 100 mM HEPES and 50 mM KCl buffer (pH 7.2), at 37°C
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23 - 170
S-adenosyl-L-homocysteine
23
S-adenosyl-L-homocysteine
-
mutant enzyme F107A, in 100 mM HEPES and 50 mM KCl buffer (pH 7.2), at 37°C
51
S-adenosyl-L-homocysteine
-
mutant enzyme H109A, in 100 mM HEPES and 50 mM KCl buffer (pH 7.2), at 37°C
170
S-adenosyl-L-homocysteine
-
wild type enzyme, in 100 mM HEPES and 50 mM KCl buffer (pH 7.2), at 37°C
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25.24
Tris
at 37°C, pH 7.5
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-
UniProt
brenda
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homodimer
x-ray crystallography
homodimer
x-ray crystallography
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enzyme alone, in complex with formycin A and in complex with adenine, hanging drop vapor diffusion method, using 0.1 M Tris pH 8.5 and 16% (w/v) polyethyleneglycol 8000, at 18°C
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. Inactive D198N mutant bound to S-adenosyl-L-homocysteine and active enzyme bound to S-(5-deoxy-D-ribos-5-yl)-L-homocysteine and adenine using 0.05 M magnesium chloride hexahydrate, 0.1 M HEPES (pH 7.5), and 30% (v/v) PEG-MME 550
-
structure in complex with transition state analogue inhibitors
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HisTrap column chromatography and Superdex 200 gel filtration
HisTrap column chromatography and Superdex 200 gel filtration
HisTrap column chromatography and Superdex 200 gel filtration
HisTrap column chromatography and Superdex 200 gel filtration
-
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expressed in Escherichia coli BL21(DE3) Rosetta cells
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Ronning, D.R.; Iacopelli, N.M.; Mishra, V.
Enzyme-ligand interactions that drive active site rearrangements in the Helicobacter pylori 5-methylthioadenosine/S-adenosylhomocysteine nucleosidase
Protein Sci.
19
2498-2510
2010
Helicobacter pylori, Helicobacter pylori (Q9ZMY2)
brenda
Mishra, V.; Ronning, D.R.
Crystal structures of the Helicobacter pylori MTAN enzyme reveal specific interactions between S-adenosylhomocysteine and the 5-alkylthio binding subsite
Biochemistry
51
9763-9772
2012
Helicobacter pylori
brenda
Harijan, R.K.; Hoff, O.; Ducati, R.G.; Firestone, R.S.; Hirsch, B.M.; Evans, G.B.; Schramm, V.L.; Tyler, P.C.
Selective inhibitors of Helicobacter pylori methylthioadenosine nucleosidase and human methylthioadenosine phosphorylase
J. Med. Chem.
62
3286-3296
2019
Helicobacter pylori (A0A1W0VQJ9), Helicobacter pylori
brenda