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Literature summary for 3.2.2.9 extracted from

  • Singh, V.; Evans, G.B.; Lenz, D.H.; Mason, J.M.; Clinch, K.; Mee, S.; Painter, G.F.; Tyler, P.C.; Furneaux, R.H.; Lee, J.E.; Howell, P.L.; Schramm, V.L.
    Femtomolar transition state analogue inhibitors of 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase from Escherichia coli (2005), J. Biol. Chem., 280, 18265-18273.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-(3-methylphenylthio)-D-ribitol
-
Escherichia coli
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-(4-methylphenylthio)-D-ribitol
-
Escherichia coli
(1S)-5-(4-chlorophenylthio)-1-(9-deaza-adenin-9-yl)-1,4-dideoxy-1,4-imino-D-ribitol
-
Escherichia coli
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(methylthiomethyl)pyrrolidine
-
Escherichia coli
(3R,4S)-4-(4-chlorophenyl-thiomethyl)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine potential antibiotic to interfere with the metabolic pathways involved in methylation, polyamine biosynthesis, methionine recycling, and quorum sensing pathways Escherichia coli
(3R,4S)-4-(benzylthiomethyl)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine
-
Escherichia coli

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information Escherichia coli 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase is involved in quorum sensing, recycling 5'-methylthioadenosine from the polyamine pathway via adenine phosphoribosyltransferase and recycling 5-methylthioribose to methionine ?
-
?

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
5'-methylthioadenosine + H2O
-
Escherichia coli 5-methylthio-D-ribose + adenine
-
?
additional information 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase is involved in quorum sensing, recycling 5'-methylthioadenosine from the polyamine pathway via adenine phosphoribosyltransferase and recycling 5-methylthioribose to methionine Escherichia coli ?
-
?
S-adenosyl-L-homocysteine + H2O
-
Escherichia coli adenine + S-ribosyl-L-homocysteine
-
?

Synonyms

Synonyms Comment Organism
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase
-
Escherichia coli

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000000000047
-
(3R,4S)-4-(4-chlorophenyl-thiomethyl)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine 25°C, pH 7.0, dissociation constant for the equilibrium complex of enzyme-inhibitor following slow-onset inhibition Escherichia coli
0.00000000046
-
(3R,4S)-4-(benzylthiomethyl)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine 25°C, pH 7.0, dissociation constant for the equilibrium complex of enzyme-inhibitor following slow-onset inhibition Escherichia coli
0.000000002
-
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(methylthiomethyl)pyrrolidine 25°C, pH 7.0, dissociation constant for the equilibrium complex of enzyme-inhibitor following slow-onset inhibition Escherichia coli
0.000000002
-
(1S)-5-(4-chlorophenylthio)-1-(9-deaza-adenin-9-yl)-1,4-dideoxy-1,4-imino-D-ribitol 25°C, pH 7.0,dissociation constant for the equilibrium complex of enzyme-inhibitor following slow-onset inhibition Escherichia coli
0.000000006
-
(1S)-5-(4-chlorophenylthio)-1-(9-deaza-adenin-9-yl)-1,4-dideoxy-1,4-imino-D-ribitol 25°C, pH 7.0, dissociation constant for the equilibrium between enzyme and inhibitor before slow-onset inhibition Escherichia coli
0.000000008
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-(4-methylphenylthio)-D-ribitol 25°C, pH 7.0, dissociation constant for the equilibrium between enzyme and inhibitor before slow-onset inhibition Escherichia coli
0.000000009
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-(3-methylphenylthio)-D-ribitol 25°C, pH 7.0,dissociation constant for the equilibrium complex of enzyme-inhibitor following slow-onset inhibition Escherichia coli
0.000000015
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-(3-methylphenylthio)-D-ribitol 25°C, pH 7.0, dissociation constant for the equilibrium between enzyme and inhibitor before slow-onset inhibition Escherichia coli
0.000000018
-
(1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-(4-methylphenylthio)-D-ribitol 25°C, pH 7.0, dissociation constant for the equilibrium between enzyme and inhibitor before slow-onset inhibition Escherichia coli
0.000000026
-
(3R,4S)-4-(4-chlorophenyl-thiomethyl)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine 25°C, pH 7.0, dissociation constant for the equilibrium between enzyme and inhibitor before slow-onset inhibition Escherichia coli
0.000000028
-
(3R,4S)-4-(benzylthiomethyl)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxypyrrolidine 25°C, pH 7.0, dissociation constant for the equilibrium between enzyme and inhibitor before slow-onset inhibition Escherichia coli
0.000000048
-
(3R,4S)-1-[(9-deazaadenin-9-yl)methyl]-3-hydroxy-4-(methylthiomethyl)pyrrolidine 25°C, pH 7.0, dissociation constant for the equilibrium between enzyme and inhibitor before slow-onset inhibition Escherichia coli