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Literature summary for 3.2.2.16 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
Search for more literature for 3.2.2.16

Cloned(Commentary)

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

Crystallization (Commentary)

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

Inhibitors

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

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

Natural Substrates/ Products (Substrates)

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

Organism

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

Purification (Commentary)

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

Reaction

Reaction Comment Organism Reaction ID
S-methyl-5'-thioadenosine + H2O = S-methyl-5-thio-D-ribose + adenine transitions state analogues, overview Escherichia coli
a
S-methyl-5'-thioadenosine + H2O = S-methyl-5-thio-D-ribose + adenine transitions state analogues, overview Salmonella enterica
a
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)

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

Synonyms

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

Temperature Optimum [°C]

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

Turnover Number [1/s]

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

pH Optimum

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

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
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
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
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
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
0.0000000055
-
 5'-4-chloro-phenylthio-immucillin-A in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Escherichia coli
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
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
0.000000038
-
 5'-4-chloro-phenylthio-immucillin-A in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Salmonella enterica
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
0.000000089
-
 methylthio-immucillin-A in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Escherichia coli
0.000000274
-
 methylthio-immucillin-A in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Salmonella enterica
0.0000003
-
 methylthio-immucillin-A in 100 mM HEPES, 50 mM KCl (pH 7.5), at 25°C Vibrio cholerae serotype O1

General Information

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

kcat/KM [mM/s]

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