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Information on EC 2.7.1.20 - adenosine kinase and Organism(s) Toxoplasma gondii and UniProt Accession Q9TVW2
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2.7.1.20 adenosine kinaseIUBMB Comments
2-Aminoadenosine can also act as acceptor.
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Word Map
- 2.7.1.20
- nucleoside
- deaminase
- purine
- amp
- adenylate
- inosine
-
salvage
- hypoxanthine
- epilepsy
-
phosphoribosyltransferase
- 5'-nucleotidase
- 5-iodotubercidin
- riboside
- deoxyadenosine
- s-adenosylhomocysteine
- deoxycytidine
- aicar
-
anticonvulsant
- tubercidin
- dipyridamole
-
neuromodulator
- ehna
-
2\'-deoxycoformycin
-
ecto-5\'-nucleotidase
- ribokinase
-
erythro-9-2-hydroxy-3-nonyl
-
adenosinergic
- 6-methylmercaptopurine
-
3hadenosine
- 2-chloroadenosine
- coformycin
-
nitrobenzylthioinosine
-
epileptogenesis
-
hypoxanthine-guanine
-
transmethylation
-
adenosine-induced
- hgprt
-
kinase-deficient
- 2'-deoxyadenosine
-
adenosine-mediated
-
3.5.4.4
- deoxycoformycin
-
non-nucleoside
- analysis
-
2.4.2.8
- 9-beta-d-arabinofuranosyladenine
-
n6-cyclopentyladenosine
-
erythro-9-2-hydroxy-3-nonyladenine
-
dado
- ara-a
- medicine
- diagnostics
-
rephosphorylation
- pharmacology
The taxonomic range for the selected organisms is: Toxoplasma gondii
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea
Synonyms
adenosine kinase, adk, ado kinase, adk-l, adk-s, rv2202c, atp:adenosine 5'-phosphotransferase, ldadk, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
adenosine kinase (phosphorylating)
-
-
-
-
kinase, adenosine (phosphorylating)
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
phospho group transfer
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
ATP:adenosine 5'-phosphotransferase
2-Aminoadenosine can also act as acceptor.
CAS REGISTRY NUMBER
COMMENTARY
9027-72-9
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
ATP + adenosine
?
the obligate intracellular parasite Toxoplasma gondii is incapable of synthesizing purine nucleotides de novo and relies completely on purines salvaged from the host cells. Adenosine is the preferred precursor and is phosphorylated by adenosine kinase (AK), the most active enzyme in adenosine metabolism in Toxoplasma gondii
-
-
?
ATP + adenosine
ADP + AMP
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enzyme shows highest activity of all enzymes involved in the adenosine salvage metabolism
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-
?
additional information
?
-
hybrid random bi-uni ping-pong uni-bi mechanism, with substrate-enzyme-cosubstrate complex formation, binding pattern indicates that binding of the substrate interferes with the binding of the cosubstrate and vice versa. For every ATP consumed, the enzyme generates three AMPs
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-
?
additional information
?
-
-
hybrid random bi-uni ping-pong uni-bi mechanism, with substrate-enzyme-cosubstrate complex formation, binding pattern indicates that binding of the substrate interferes with the binding of the cosubstrate and vice versa. For every ATP consumed, the enzyme generates three AMPs
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
ATP + adenosine
?
the obligate intracellular parasite Toxoplasma gondii is incapable of synthesizing purine nucleotides de novo and relies completely on purines salvaged from the host cells. Adenosine is the preferred precursor and is phosphorylated by adenosine kinase (AK), the most active enzyme in adenosine metabolism in Toxoplasma gondii
-
-
?
ATP + adenosine
ADP + AMP
-
enzyme shows highest activity of all enzymes involved in the adenosine salvage metabolism
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
adenosine
substrate inhibition, presence of ATP relieves substrate inhibition by adenosine
ADP
noncompetitive with adenosine, ADP and ATP show additive effects
ATP
noncompetitive with adenosine, ADP and ATP show additive effects
additional information
-
IC50 values and toxicities, i.e. rates of survival, of the 6-benzylthioinosine derivatives in wild-type strain RH and in the mutant strain TgAK-3 in human fibrobalsts, effects of 6-benzylthioinosine and derivatives 2-cyano-6-benzylthioinosine and 2,4-dichloro-6-benzylthioinosine on survival of mice infected with the wild-type strain RH, overview
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additional information
-
all the 7-deaza-6-benzylthioinosine analogues showed a selective antitoxoplasmic effect against wild type parasites, but not mutants lacking adenosine kinase
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.15
2,4,6-trimethyl-6-benzylthioinosine
-
pH 7.4, 37°C, recombinant enzyme
0.0377
2-chloro-6-fluoro-6-benzylthioinosine
-
pH 7.4, 37°C, recombinant enzyme
0.0029
3-trifluoromethyl-6-benzylthioinosine
-
pH 7.4, 37°C, recombinant enzyme
0.141
4-trifluoromethoxy-6-benzylthioinosine
-
pH 7.4, 37°C, recombinant enzyme
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0161
carbocyclic 6-(2,3,4-trimethylbenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0186
carbocyclic 6-(2,4-dichlorobenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0136
carbocyclic 6-(2-chloro-6-fluorobenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.02
carbocyclic 6-(2-chlorobenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0389
carbocyclic 6-(2-fluorobenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0197
carbocyclic 6-(2-methylbenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0144
carbocyclic 6-(3,4-dichlorobenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0238
carbocyclic 6-(3-methylbenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0197
carbocyclic 6-(3-nitrobenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0191
carbocyclic 6-(3-trifluoromethylbenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0183
carbocyclic 6-(4-bromobenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0145
carbocyclic 6-(4-chlorobenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.049
carbocyclic 6-(4-cyanobenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0232
carbocyclic 6-(4-fluorobenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0121
carbocyclic 6-(4-methoxybenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0119
carbocyclic 6-(4-methylbenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0146
carbocyclic 6-(4-methylsulfonylbenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0428
carbocyclic 6-(4-nitrobenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.021
carbocyclic 6-(4-trifluoromethoxybenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0128
carbocyclic 6-(p-methoxycarbonylbenzylthio)inosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0191
carbocyclic 6-benzylthioinosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0204
6-benzylthioinosine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0161
pyrimethamine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
0.0273
Sulfadiazine
Toxoplasma gondii
-
in 50 mM Tris-HCl, pH 7.5, 5 mM MgCl2; 1 mM dithiothreitol, 25 mM NaF, at 37°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). ADK_TOXGO
363
0
38356
Swiss-Prot
other Location (Reliability: 3)
PDB
SCOP
CATH
UNIPROT
ORGANISM
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
hanging-drop vapor-diffusion method, structure of a binary complex of adenosine kinase and the nonhydrolysable ATP analog AMP-PCP is determined to 1.1 A resolution
hanging-drop vapor-diffusion method, structures of the Toxoplasma gondii adenosine kinase-N6,N6-dimethyladenosine complex, the adenosine kinase/N6,N6-dimethyladenosine/beta,gamma-methyleneadenosine 5'-triphosphate complex, the adenosine kinase6-methyl mercaptopurine riboside complex and the adenosine kinase/6-methyl mercaptopurine riboside/beta,gamma-methyleneadenosine 5'-triphosphate complex are determined to 1.35, 1.35, 1.75 and 1.75 A resolution, respectively
hanging-drop vapor-diffusion method, the structures of the Toxoplasma gondii adenosine kinaseN6,N6-dimethyladenosine complex, the adenosine kinase-N6,N6-dimethyladenosine-AMP-PCP complex, the adenosine kinase-6-methyl mercaptopurine riboside complex and the adenosine kinase-6-methyl mercaptopurine riboside-AMP-PCP complex are determined to 1.35, 1.35, 1.75 and 1.75 A resolution, respectively
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-75°C, pure enzyme, 20 mM Tris-HCl, pH 8.0, 15 mM 2-mercaptoethanol, stable for months
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant enzyme from Escherichia coli strain BL21(DE3) by 3 steps of ion exchange chromatography, to homogeneity
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
overexpression of the soluble enzyme in Escherichia coli strain BL21(DE3)
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
medicine
medicine
adenosine kinase represents a potential chemotherapeutic target for the treatment of Toxoplasma gondii infections
medicine
siRNAs transfected into cells can work efficiently to regulate gene expression in Toxoplasma gondii. The application of siRNA in interrupting gene expression in Toxoplasma gondii would be useful for elucidating gene function as a step toward development of antitoxoplasmasis vaccines and therapeutic reagents
medicine
-
the enzyme is an excellent target for chemotherapy with 6-substituted purine nucleosides being potential selective antitoxoplasmic agents
medicine
-
Toxoplasma gondii adenosine kinase is an excellent target for chemotherapy and 7-deaza-6-benzylthioinosines are potential antitoxoplasmic agents
medicine
-
transfection of dsRNAs into cells can efficiently regulate gene expression in Toxoplasma gondii. Application of dsRNA to disrupt gene expression in Toxoplasma gondii would be useful for elucidating gene function as a step towards the development of therapeutic reagents
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Recacha, R.; Talalaev, A.; DeLucas, L.J.; Chattopadhyay, D.
Toxoplasma gondii adenosine kinase: expression, purification, characterization, crystallization and preliminary crystallographic analysis
Acta Crystallogr. Sect. D
56
76-78
2000
Toxoplasma gondii
Schumacher, M.A.; Scott, D.M.; Mathews, I.I.; Ealick, S.E.; Roos, D.S.; Ullman, B.; Brennan, R.G.
Crystal structures of Toxoplasma gondii adenosine kinase reveal a novel catalytic mechanism and prodrug binding
J. Mol. Biol.
296
549-567
2000
Toxoplasma gondii
Cook, W.J.; DeLucas, L.J.; Chattopadhyay, D.
Crystal structure of adenosine kinase from Toxoplasma gondii at 1.8 A resolution
Protein Sci.
9
704-712
2000
Toxoplasma gondii
Rais, R.H.; Al Safarjalani, O.N.; Yadav, V.; Guarcello, V.; Kirk, M.; Chu, C.K.; Naguib, F.N.; el Kouni, M.H.
6-Benzylthioinosine analogues as subversive substrate of Toxoplasma gondii adenosine kinase: activities and selective toxicities
Biochem. Pharmacol.
69
1409-1419
2005
Toxoplasma gondii
Zhang, Y.; El Kouni, M.H.; Ealick, S.E.
Structure of Toxoplasma gondii adenosine kinase in complex with an ATP analog at 1.1 A resolution
Acta Crystallogr. Sect. D
62
140-145
2006
Toxoplasma gondii (Q9TVW2), Toxoplasma gondii
Zhang, Y.; El Kouni, M.H.; Ealick, S.E.
Substrate analogs induce an intermediate conformational change in Toxoplasma gondii adenosine kinase
Acta Crystallogr. Sect. D
63
126-134
2007
Toxoplasma gondii (Q9TVW2), Toxoplasma gondii
Al Safarjalani, O.N.; Rais, R.H.; Ah Kim, Y.; Chu, C.K.; Naguib, F.N.; El Kouni, M.H.
7-Deaza-6-benzylthioinosine analogues as subversive substrate of Toxoplasma gondii adenosine kinase: Activities and selective toxicities
Biochem. Pharmacol.
76
958-966
2008
Toxoplasma gondii
Yu, L.; Gao, Y.F.; Qiao, Z.P.; Li, C.L.; Li, X.; Shen, J.L.
Toxoplasma gondii: siRNA can mediate the suppression of adenosine kinase expression
Exp. Parasitol.
118
96-102
2008
Toxoplasma gondii (Q9TVW2), Toxoplasma gondii
Kim, Y.A.; Sharon, A.; Chu, C.K.; Rais, R.H.; Al Safarjalani, O.N.; Naguib, F.N.; el Kouni, M.H.
Structure-activity relationships of 7-deaza-6-benzylthioinosine analogues as ligands of Toxoplasma gondii adenosine kinase
J. Med. Chem.
51
3934-3945
2008
Toxoplasma gondii
Yu, L.; Gao, Y.F.; Li, X.; Qiao, Z.P.; Shen, J.L.
Double-stranded RNA specific to adenosine kinase and hypoxanthine-xanthine-guanine-phosphoribosyltransferase retards growth of Toxoplasma gondii
Parasitol. Res.
104
377-383
2008
Toxoplasma gondii
Al Safarjalani, O.N.; Rais, R.H.; Kim, Y.A.; Chu, C.K.; Naguib, F.N.; El Kouni, M.H.
Carbocyclic 6-benzylthioinosine analogues as subversive substrates of Toxoplasma gondii adenosine kinase: biological activities and selective toxicities
Biochem. Pharmacol.
80
955-963
2010
Toxoplasma gondii
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