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Literature summary for 3.2.2.26 extracted from

  • Ducati, R.G.; Harijan, R.K.; Cameron, S.A.; Tyler, P.C.; Evans, G.B.; Schramm, V.L.
    Transition-state analogues of Campylobacter jejuni 5'-methylthioadenosine nucleosidase (2018), ACS Chem. Biol., 13, 3173-3183 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 3.2.2.26

Cloned(Commentary)

Cloned (Comment) Organism
expressed in Escherichia coli BL21(DE3) cells Campylobacter jejuni subsp. jejuni

Crystallization (Commentary)

Crystallization (Comment) Organism
free enzyme or in complex with inhibitors, sitting drop vapor diffusion method Campylobacter jejuni subsp. jejuni

Inhibitors

Inhibitors Comment Organism Structure
(2R)-2-[[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-(methylsulfanyl)propan-1-ol
-
 Campylobacter jejuni subsp. jejuni
(2R)-2-[[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-[(pyrazin-2-yl)sulfanyl]propan-1-ol
-
 Campylobacter jejuni subsp. jejuni
(2S)-2-[[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]octan-1-ol
-
 Campylobacter jejuni subsp. jejuni
(2S,3S,4R,5S)-2-(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)-5-[(methylsulfanyl)methyl]pyrrolidine-3,4-diol
-
 Campylobacter jejuni subsp. jejuni
(2S,3S,4R,5S)-2-(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)-5-[[(4-chlorophenyl)sulfanyl]methyl]pyrrolidine-3,4-diol
-
 Campylobacter jejuni subsp. jejuni
(2S,3S,4R,5S)-2-(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)-5-[[(naphthalen-1-yl)sulfanyl]methyl]pyrrolidine-3,4-diol
-
 Campylobacter jejuni subsp. jejuni
(3R,4R)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-(hydroxymethyl)pyrrolidin-3-ol
-
 Campylobacter jejuni subsp. jejuni
(3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-(adamant-1-yl)sulfanyl]methyl]pyrrolidin-3-ol
-
 Campylobacter jejuni subsp. jejuni
(3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-([[2-(2-hydroxyethoxy)ethyl]sulfanyl]methyl)pyrrolidin-3-ol
-
 Campylobacter jejuni subsp. jejuni
(3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-butylpyrrolidin-3-ol
-
 Campylobacter jejuni subsp. jejuni
(3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-ethylpyrrolidin-3-ol
-
 Campylobacter jejuni subsp. jejuni
(3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-methylpyrrolidin-3-ol
-
 Campylobacter jejuni subsp. jejuni
(3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-propylpyrrolidin-3-ol
-
 Campylobacter jejuni subsp. jejuni
(3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(butylsulfanyl)methyl]pyrrolidin-3-ol
-
 Campylobacter jejuni subsp. jejuni
(3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(cyclohexylsulfanyl)methyl]pyrrolidin-3-ol
-
 Campylobacter jejuni subsp. jejuni
(3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(hexylsulfanyl)methyl]pyrrolidin-3-ol
-
 Campylobacter jejuni subsp. jejuni
(3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(methylsulfanyl)methyl]pyrrolidin-3-ol
-
 Campylobacter jejuni subsp. jejuni
(3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(phenylsulfanyl)methyl]pyrrolidin-3-ol
-
 Campylobacter jejuni subsp. jejuni
(3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[2-(hexylsulfanyl)ethyl]pyrrolidin-3-ol
-
 Campylobacter jejuni subsp. jejuni
(3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[2-[2-(2-hydroxyethoxy)ethoxy]ethyl]pyrrolidin-3-ol
-
 Campylobacter jejuni subsp. jejuni
(3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[[(4-chlorophenyl)sulfanyl]methyl]pyrrolidin-3-ol
-
 Campylobacter jejuni subsp. jejuni
(3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[[(pyrazin-2-yl)sulfanyl]methyl]pyrrolidin-3-ol
-
 Campylobacter jejuni subsp. jejuni
(3S,4R,5R)-2-(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(hydroxymethyl)pyrrolidine-3,4-diol
-
 Campylobacter jejuni subsp. jejuni
(3S,4R,5R)-2-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-5-(hydroxymethyl)pyrrolidine-3,4-diol
-
 Campylobacter jejuni subsp. jejuni
3-(3-[(3S,4R)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-hydroxypyrrolidin-3-yl]propanoyl)benzoic acid
-
 Campylobacter jejuni subsp. jejuni
3-[3-[(2R,3R,4S,5S)-5-(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)-3,4-dihydroxypyrrolidin-2-yl]propanoyl]benzoic acid
-
 Campylobacter jejuni subsp. jejuni
7-(5-S-methyl-5-thio-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
-
 Campylobacter jejuni subsp. jejuni
gentamicin
-
 Campylobacter jejuni subsp. jejuni
[(3S,4R)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-hydroxypyrrolidin-3-yl]methionine
-
 Campylobacter jejuni subsp. jejuni

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0035
-
 6-amino-6-deoxyfutalosine at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.0071
-
 5'-methylthioadenosine at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.0075
-
 adenosine at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.0122
-
 S-5'-adenosyl-L-homocysteine at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.0214
-
 5'-deoxyadenosine at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni

Organism

Organism UniProt Comment Textmining
Campylobacter jejuni subsp. jejuni Q0PC20
-
-
Campylobacter jejuni subsp. jejuni ATCC 700819 Q0PC20
-
-

Purification (Commentary)

Purification (Comment) Organism
Ni-NTA column chromatography Campylobacter jejuni subsp. jejuni

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
5'-deoxyadenosine + H2O
-
 Campylobacter jejuni subsp. jejuni ?
-
 ?
5'-deoxyadenosine + H2O
-
 Campylobacter jejuni subsp. jejuni ATCC 700819 ?
-
 ?
5'-methylthioadenosine + H2O
-
 Campylobacter jejuni subsp. jejuni ?
-
 ?
5'-methylthioadenosine + H2O
-
 Campylobacter jejuni subsp. jejuni ATCC 700819 ?
-
 ?
6-amino-6-deoxyfutalosine + H2O
-
 Campylobacter jejuni subsp. jejuni dehypoxanthine futalosine + adenine
-
 ?
6-amino-6-deoxyfutalosine + H2O
-
 Campylobacter jejuni subsp. jejuni ATCC 700819 dehypoxanthine futalosine + adenine
-
 ?
adenosine + H2O
-
 Campylobacter jejuni subsp. jejuni ?
-
 ?
adenosine + H2O
-
 Campylobacter jejuni subsp. jejuni ATCC 700819 ?
-
 ?
S-5'-adenosyl-L-homocysteine + H2O
-
 Campylobacter jejuni subsp. jejuni ?
-
 ?
S-5'-adenosyl-L-homocysteine + H2O
-
 Campylobacter jejuni subsp. jejuni ATCC 700819 ?
-
 ?

Synonyms

Synonyms Comment Organism
5'-methylthioadenosine nucleosidase
-
 Campylobacter jejuni subsp. jejuni
MTAN
-
 Campylobacter jejuni subsp. jejuni

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.27
-
 6-amino-6-deoxyfutalosine at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.3
-
 adenosine at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.55
-
 S-5'-adenosyl-L-homocysteine at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.8
-
 5'-methylthioadenosine at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.92
-
 5'-deoxyadenosine at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00000065
-
 (3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(hexylsulfanyl)methyl]pyrrolidin-3-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.00000075
-
 (3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(butylsulfanyl)methyl]pyrrolidin-3-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.0000014
-
 (3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[[(pyrazin-2-yl)sulfanyl]methyl]pyrrolidin-3-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.0000014
-
 (3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-butylpyrrolidin-3-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.000002
-
 (3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[2-(hexylsulfanyl)ethyl]pyrrolidin-3-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.0000022
-
 (3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(cyclohexylsulfanyl)methyl]pyrrolidin-3-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.0000029
-
 (3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-propylpyrrolidin-3-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.0000029
-
 (3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(methylsulfanyl)methyl]pyrrolidin-3-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.0000031
-
 (3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[[(4-chlorophenyl)sulfanyl]methyl]pyrrolidin-3-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.0000032
-
 (3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-([[2-(2-hydroxyethoxy)ethyl]sulfanyl]methyl)pyrrolidin-3-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.000004
-
 (3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(phenylsulfanyl)methyl]pyrrolidin-3-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.0000062
-
 (2S)-2-[[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]octan-1-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.00001
-
 (3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-ethylpyrrolidin-3-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.000014
-
 (2S,3S,4R,5S)-2-(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)-5-[(methylsulfanyl)methyl]pyrrolidine-3,4-diol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.000019
-
 (3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-(adamant-1-yl)sulfanyl]methyl]pyrrolidin-3-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.000024
-
 [(3S,4R)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-hydroxypyrrolidin-3-yl]methionine at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.000028
-
 (2S,3S,4R,5S)-2-(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)-5-[[(4-chlorophenyl)sulfanyl]methyl]pyrrolidine-3,4-diol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.000055
-
 (3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-methylpyrrolidin-3-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.000106
-
 3-(3-[(3S,4R)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-hydroxypyrrolidin-3-yl]propanoyl)benzoic acid at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.000216
-
 (2R)-2-[[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-(methylsulfanyl)propan-1-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.000422
-
 (2S,3S,4R,5S)-2-(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)-5-[[(naphthalen-1-yl)sulfanyl]methyl]pyrrolidine-3,4-diol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.000946
-
 (2R)-2-[[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]-3-[(pyrazin-2-yl)sulfanyl]propan-1-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.0017
-
 (3R,4S)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[2-[2-(2-hydroxyethoxy)ethoxy]ethyl]pyrrolidin-3-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.0026
-
 (3R,4R)-1-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-(hydroxymethyl)pyrrolidin-3-ol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.0027
-
 3-[3-[(2R,3R,4S,5S)-5-(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)-3,4-dihydroxypyrrolidin-2-yl]propanoyl]benzoic acid at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.013
-
 (3S,4R,5R)-2-[(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-5-(hydroxymethyl)pyrrolidine-3,4-diol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.014
-
 (3S,4R,5R)-2-(4-amino-5,7a-dihydro-4aH-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(hydroxymethyl)pyrrolidine-3,4-diol at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
0.022
-
 7-(5-S-methyl-5-thio-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0021
-
 at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni gentamicin

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
40
-
 adenosine at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
43
-
 5'-deoxyadenosine at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
46
-
 S-5'-adenosyl-L-homocysteine at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
78
-
 6-amino-6-deoxyfutalosine at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni
113
-
 5'-methylthioadenosine at pH 7.4 and 25°C Campylobacter jejuni subsp. jejuni