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Literature summary extracted from

  • Thomas, K.; Haapalainen, A.M.; Burgos, E.S.; Evans, G.B.; Tyler, P.C.; Gulab, S.; Guan, R.; Schramm, V.L.
    Femtomolar inhibitors bind to 5'-methylthioadenosine nucleosidases with favorable enthalpy and entropy (2012), Biochemistry, 51, 7541-7550.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
3.2.2.16 expressed in Escherichia coli BL21(DE3) cells Escherichia coli
3.2.2.16 expressed in Escherichia coli BL21(DE3) cells Salmonella enterica
3.2.2.16 expressed in Escherichia coli BL21(DE3) cells Vibrio cholerae serotype O1
3.2.2.16 recombinant expression of N-terminally His6-tagged enzyme in Escherichia coli strain BL21 Star(DE3) Escherichia coli
3.2.2.16 recombinant expression of N-terminally His6-tagged enzyme in Escherichia coli strain BL21 Star(DE3) Vibrio cholerae serotype O1

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
3.2.2.16 crystal structure analysis, PDB entry 1Y6Q and PDB entry 1Z5P Escherichia coli

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.2.2.16 (4S,5S)-2-(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-5-[(methylsulfanyl)methyl]-1,2-thiazolidin-4-ol
-
 Salmonella enterica
3.2.2.16 (4S,5S)-2-(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-5-[(methylsulfanyl)methyl]-1,2-thiazolidin-4-ol
-
 Vibrio cholerae serotype O1
3.2.2.16 1'-aza-4'-deaza-2'-deoxy-1'-(9-methylene)-immucillin-A
-
 Escherichia coli
3.2.2.16 5'-4-chloro-phenylthio-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-A
-
 Escherichia coli
3.2.2.16 5'-4-chloro-phenylthio-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-A
-
 Salmonella enterica
3.2.2.16 5'-4-chloro-phenylthio-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-A
-
 Vibrio cholerae serotype O1
3.2.2.16 5'-4-chloro-phenylthio-immucillin-A
-
 Escherichia coli
3.2.2.16 5'-4-chloro-phenylthio-immucillin-A
-
 Salmonella enterica
3.2.2.16 5'-4-chloro-phenylthio-immucillin-A
-
 Vibrio cholerae serotype O1
3.2.2.16 immucillin-A
-
 Escherichia coli
3.2.2.16 immucillin-A
-
 Salmonella enterica
3.2.2.16 immucillin-A
-
 Vibrio cholerae serotype O1
3.2.2.16 methylthio-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene) -immucillin-A
-
 Salmonella enterica
3.2.2.16 methylthio-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-A
-
 Escherichia coli
3.2.2.16 methylthio-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-A
-
 Vibrio cholerae serotype O1
3.2.2.16 methylthio-immucillin-A
-
 Escherichia coli
3.2.2.16 methylthio-immucillin-A
-
 Salmonella enterica
3.2.2.16 methylthio-immucillin-A
-
 Vibrio cholerae serotype O1
3.2.2.16 additional information inhibitor design and synthesis informed by transition state analysis have developed femtomolar inhibitors, thermodynamic analyses of transition state analogues, overview Escherichia coli
3.2.2.16 additional information inhibitor design and synthesis informed by transition state analysis have developed femtomolar inhibitors, thermodynamic analyses of transition state analogues, overview Salmonella enterica
3.2.2.16 additional information inhibitor design and synthesis informed by transition state analysis have developed femtomolar inhibitors, thermodynamic analyses of transition state analogues, overview Vibrio cholerae serotype O1

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.2.2.16 0.00000019
-
 S-methyl-5'-thioadenosine in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Escherichia coli
3.2.2.16 0.00000036
-
 S-methyl-5'-thioadenosine in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Vibrio cholerae serotype O1
3.2.2.16 0.0000004
-
 S-methyl-5'-thioadenosine in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Salmonella enterica
3.2.2.16 0.00019
-
 5'-methylthioadenosine pH 7.5, 25°C, recombinant enzyme Escherichia coli
3.2.2.16 0.00036
-
 5'-methylthioadenosine pH 7.5, 25°C, recombinant enzyme Vibrio cholerae serotype O1
3.2.2.16 0.0004
-
 5'-methylthioadenosine pH 7.5, 25°C, recombinant enzyme Salmonella enterica

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.2.2.16 5'-methylthioadenosine + H2O Escherichia coli
-
 adenine + S-methyl-5-thio-D-ribose
-
 ?
3.2.2.16 5'-methylthioadenosine + H2O Salmonella enterica
-
 adenine + S-methyl-5-thio-D-ribose
-
 ?
3.2.2.16 5'-methylthioadenosine + H2O Vibrio cholerae serotype O1
-
 adenine + S-methyl-5-thio-D-ribose
-
 ?
3.2.2.16 additional information Escherichia coli the enzyme catalyzes the hydrolytic cleavage of adenine from methylthioadenosine ?
-
 ?
3.2.2.16 additional information Salmonella enterica the enzyme catalyzes the hydrolytic cleavage of adenine from methylthioadenosine ?
-
 ?
3.2.2.16 additional information Vibrio cholerae serotype O1 the enzyme catalyzes the hydrolytic cleavage of adenine from methylthioadenosine ?
-
 ?
3.2.2.16 S-methyl-5'-thioadenosine + H2O Escherichia coli
-
 S-methyl-5-thio-D-ribose + adenine
-
 ?
3.2.2.16 S-methyl-5'-thioadenosine + H2O Salmonella enterica
-
 S-methyl-5-thio-D-ribose + adenine
-
 ?
3.2.2.16 S-methyl-5'-thioadenosine + H2O Vibrio cholerae serotype O1
-
 S-methyl-5-thio-D-ribose + adenine
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.2.2.16 Escherichia coli
-
-
-
3.2.2.16 Salmonella enterica
-
-
-
3.2.2.16 Vibrio cholerae serotype O1
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
3.2.2.16 Ni-NTA column chromatography Escherichia coli
3.2.2.16 Ni-NTA column chromatography Salmonella enterica
3.2.2.16 Ni-NTA column chromatography Vibrio cholerae serotype O1
3.2.2.16 recombinant N-terminally His6-tagged enzyme from Escherichia coli strain BL21 Star(DE3) by nickel affinity chromatography Escherichia coli
3.2.2.16 recombinant N-terminally His6-tagged enzyme from Escherichia coli strain BL21 Star(DE3) by nickel affinity chromatography Vibrio cholerae serotype O1

Reaction

EC Number Reaction Comment Organism Reaction ID
3.2.2.16 S-methyl-5'-thioadenosine + H2O = S-methyl-5-thio-D-ribose + adenine transitions state analogues, overview Escherichia coli
a
3.2.2.16 S-methyl-5'-thioadenosine + H2O = S-methyl-5-thio-D-ribose + adenine transitions state analogues, overview Salmonella enterica
a
3.2.2.16 S-methyl-5'-thioadenosine + H2O = S-methyl-5-thio-D-ribose + adenine transitions state analogues, overview Vibrio cholerae serotype O1
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.2.2.16 5'-methylthioadenosine + H2O
-
 Escherichia coli adenine + S-methyl-5-thio-D-ribose
-
 ?
3.2.2.16 5'-methylthioadenosine + H2O
-
 Salmonella enterica adenine + S-methyl-5-thio-D-ribose
-
 ?
3.2.2.16 5'-methylthioadenosine + H2O
-
 Vibrio cholerae serotype O1 adenine + S-methyl-5-thio-D-ribose
-
 ?
3.2.2.16 additional information the enzyme catalyzes the hydrolytic cleavage of adenine from methylthioadenosine Escherichia coli ?
-
 ?
3.2.2.16 additional information the enzyme catalyzes the hydrolytic cleavage of adenine from methylthioadenosine Salmonella enterica ?
-
 ?
3.2.2.16 additional information the enzyme catalyzes the hydrolytic cleavage of adenine from methylthioadenosine Vibrio cholerae serotype O1 ?
-
 ?
3.2.2.16 S-methyl-5'-thioadenosine + H2O
-
 Escherichia coli S-methyl-5-thio-D-ribose + adenine
-
 ?
3.2.2.16 S-methyl-5'-thioadenosine + H2O
-
 Salmonella enterica S-methyl-5-thio-D-ribose + adenine
-
 ?
3.2.2.16 S-methyl-5'-thioadenosine + H2O
-
 Vibrio cholerae serotype O1 S-methyl-5-thio-D-ribose + adenine
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.2.2.16 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase
-
 Escherichia coli
3.2.2.16 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase
-
 Salmonella enterica
3.2.2.16 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase
-
 Vibrio cholerae serotype O1
3.2.2.16 MTAN
-
 Escherichia coli
3.2.2.16 MTAN
-
 Salmonella enterica
3.2.2.16 MTAN
-
 Vibrio cholerae serotype O1

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.2.2.16 25
-
 assay at Escherichia coli
3.2.2.16 25
-
 assay at Salmonella enterica
3.2.2.16 25
-
 assay at Vibrio cholerae serotype O1

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
3.2.2.16 2.3
-
 5'-methylthioadenosine pH 7.5, 25°C, recombinant enzyme Escherichia coli
3.2.2.16 2.3
-
 S-methyl-5'-thioadenosine in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Escherichia coli
3.2.2.16 4.2
-
 5'-methylthioadenosine pH 7.5, 25°C, recombinant enzyme Vibrio cholerae serotype O1
3.2.2.16 4.2
-
 S-methyl-5'-thioadenosine in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Vibrio cholerae serotype O1
3.2.2.16 20
-
 5'-methylthioadenosine pH 7.5, 25°C, recombinant enzyme Salmonella enterica
3.2.2.16 20
-
 S-methyl-5'-thioadenosine in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Salmonella enterica

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.2.2.16 7.5
-
 assay at Escherichia coli
3.2.2.16 7.5
-
 assay at Salmonella enterica
3.2.2.16 7.5
-
 assay at Vibrio cholerae serotype O1

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
3.2.2.16 0.00000000004
-
 5'-4-chloro-phenylthio-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-A in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Escherichia coli
3.2.2.16 0.00000000011
-
 methylthio-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-A in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Escherichia coli
3.2.2.16 0.0000000027
-
 5'-4-chloro-phenylthio-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-A in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Salmonella enterica
3.2.2.16 0.000000005
-
 methylthio-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene) -immucillin-A in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Salmonella enterica
3.2.2.16 0.0000000055
-
 5'-4-chloro-phenylthio-immucillin-A in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Escherichia coli
3.2.2.16 0.0000000093
-
 5'-4-chloro-phenylthio-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-A in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Vibrio cholerae serotype O1
3.2.2.16 0.0000000125
-
 methylthio-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-A in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Vibrio cholerae serotype O1
3.2.2.16 0.000000038
-
 5'-4-chloro-phenylthio-immucillin-A in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Salmonella enterica
3.2.2.16 0.000000059
-
 5'-4-chloro-phenylthio-immucillin-A in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Vibrio cholerae serotype O1
3.2.2.16 0.000000089
-
 methylthio-immucillin-A in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Escherichia coli
3.2.2.16 0.000000274
-
 methylthio-immucillin-A in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Salmonella enterica
3.2.2.16 0.0000003
-
 methylthio-immucillin-A in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Vibrio cholerae serotype O1

General Information

EC Number General Information Comment Organism
3.2.2.16 malfunction enzyme inhibition disrupts the production of autoinducers, the chemical messengers required for quorum sensing Escherichia coli
3.2.2.16 malfunction enzyme inhibition disrupts the production of autoinducers, the chemical messengers required for quorum sensing Salmonella enterica
3.2.2.16 malfunction enzyme inhibition disrupts the production of autoinducers, the chemical messengers required for quorum sensing Vibrio cholerae serotype O1

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
3.2.2.16 0.00012
-
 S-methyl-5'-thioadenosine in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Escherichia coli
3.2.2.16 0.00012
-
 S-methyl-5'-thioadenosine in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Vibrio cholerae serotype O1
3.2.2.16 0.5
-
 5'-methylthioadenosine pH 7.5, 25°C, recombinant enzyme Salmonella enterica
3.2.2.16 1.2
-
 5'-methylthioadenosine pH 7.5, 25°C, recombinant enzyme Vibrio cholerae serotype O1
3.2.2.16 1200
-
 5'-methylthioadenosine pH 7.5, 25°C, recombinant enzyme Escherichia coli
3.2.2.16 50000
-
 S-methyl-5'-thioadenosine in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Salmonella enterica