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Literature summary for 3.2.2.30 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 3.2.2.30

Cloned(Commentary)

Cloned (Comment) Organism
expression in Escherichia coli Campylobacter jejuni subsp. jejuni serotype O:2

Crystallization (Commentary)

Crystallization (Comment) Organism
structure of apoenzyme at 1.25 A, and five enzyme complexes with transition-state analogues at 1.42 to 1.95 A resolution. Inhibitor binding induces a loop movement to create a closed catalytic site with Asp196 and Ile152 providing purine leaving group activation and Arg192 and Glu12 activating the water nucleophile Campylobacter jejuni subsp. jejuni serotype O:2

Inhibitors

Inhibitors Comment Organism Structure
(3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(butylsulfanyl)methyl]pyrrolidin-3-ol transition state analogue, compound inhibits bacterial growth with IC50 values in the low micromolar range Campylobacter jejuni subsp. jejuni serotype O:2
(3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(hexylsulfanyl)methyl]pyrrolidin-3-ol transition state analogue, compound inhibits bacterial growth with IC50 values in the low micromolar range Campylobacter jejuni subsp. jejuni serotype O:2
(3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[[(2,3-dihydropyrazin-2-yl)sulfanyl]methyl]pyrrolidin-3-ol transition state analogue, compound inhibits bacterial growth with IC50 values in the low micromolar range Campylobacter jejuni subsp. jejuni serotype O:2

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0035
-
 6-amino-6-deoxyfutalosine pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2
0.0071
-
 5'-methylthioadenosine pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2
0.0075
-
 adenosine pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2
0.0122
-
 S-5'-adenosyl-L-homocysteine pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2
0.0214
-
 5'-deoxyadenosine pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2

Organism

Organism UniProt Comment Textmining
Campylobacter jejuni subsp. jejuni serotype O:2 Q0PC20
-
-
Campylobacter jejuni subsp. jejuni serotype O:2 ATCC 700819 Q0PC20
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
5'-deoxyadenosine + H2O
-
 Campylobacter jejuni subsp. jejuni serotype O:2 adenine + 5-deoxyribose
-
 ?
5'-deoxyadenosine + H2O
-
 Campylobacter jejuni subsp. jejuni serotype O:2 ATCC 700819 adenine + 5-deoxyribose
-
 ?
5'-methylthioadenosine + H2O
-
 Campylobacter jejuni subsp. jejuni serotype O:2 adenine + S-methyl-5'-thioribose
-
 ?
5'-methylthioadenosine + H2O
-
 Campylobacter jejuni subsp. jejuni serotype O:2 ATCC 700819 adenine + S-methyl-5'-thioribose
-
 ?
6-amino-6-deoxyfutalosine + H2O
-
 Campylobacter jejuni subsp. jejuni serotype O:2 adenine + dehypoxanthinyl futalosine
-
 ?
6-amino-6-deoxyfutalosine + H2O
-
 Campylobacter jejuni subsp. jejuni serotype O:2 ATCC 700819 adenine + dehypoxanthinyl futalosine
-
 ?
adenosine + H2O
-
 Campylobacter jejuni subsp. jejuni serotype O:2 adenine + D-ribose
-
 ?
adenosine + H2O
-
 Campylobacter jejuni subsp. jejuni serotype O:2 ATCC 700819 adenine + D-ribose
-
 ?
S-5'-adenosyl-L-homocysteine + H2O
-
 Campylobacter jejuni subsp. jejuni serotype O:2 adenine + S-ribosyl-L-homocysteine
-
 ?
S-5'-adenosyl-L-homocysteine + H2O
-
 Campylobacter jejuni subsp. jejuni serotype O:2 ATCC 700819 adenine + S-ribosyl-L-homocysteine
-
 ?

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.27
-
 6-amino-6-deoxyfutalosine pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2
0.3
-
 adenosine pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2
0.55
-
 S-5'-adenosyl-L-homocysteine pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2
0.8
-
 5'-methylthioadenosine pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2
0.92
-
 5'-deoxyadenosine pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0000033
-
 (3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(hexylsulfanyl)methyl]pyrrolidin-3-ol pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2
0.0000041
-
 (3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(butylsulfanyl)methyl]pyrrolidin-3-ol pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2
0.0000057
-
 (3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[[(2,3-dihydropyrazin-2-yl)sulfanyl]methyl]pyrrolidin-3-ol pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
40
-
 adenosine pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2
43
-
 5'-deoxyadenosine pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2
46
-
 S-5'-adenosyl-L-homocysteine pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2
78
-
 6-amino-6-deoxyfutalosine pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2
113
-
 5'-methylthioadenosine pH 7.4, 25°C Campylobacter jejuni subsp. jejuni serotype O:2