Information on EC 2.4.2.22 - xanthine phosphoribosyltransferase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
2.4.2.22
-
RECOMMENDED NAME
GeneOntology No.
xanthine phosphoribosyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
XMP + diphosphate = 5-phospho-alpha-D-ribose 1-diphosphate + xanthine
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pentosyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
Metabolic pathways
-
-
purine metabolism
-
-
Purine metabolism
-
-
xanthine and xanthosine salvage
-
-
SYSTEMATIC NAME
IUBMB Comments
XMP:diphosphate 5-phospho-alpha-D-ribosyltransferase
-
CAS REGISTRY NUMBER
COMMENTARY hide
9023-10-3
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
Uniprot
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
-
Sphi609 cells expressing wild-type XPRT grow in minimal medium supplemented with xanthine but not in medium containing hypoxanthine or guanine. In contrast, Escherichia coli Sphi609 transformed with E198D or E215D exhibit vigorous growth with xanthine or hypoxanthine but notably less growth with guanine. Sphi609 transformants expressing E215Q or E198D/E215D proliferate robustly in xanthine, hypoxanthine, and guanine
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
5-phospho-alpha-D-ribose 1-diphosphate + 4,6-dihydroxypyrazolo[3,4-d]pyrimidine
?
show the reaction diagram
-
at 0.064% of the activity with xanthine
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 5,7-dihydroxy-v-triazolo[4,5-d]pyrimidine
?
show the reaction diagram
-
at 16.8% of the activity with xanthine
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + adenine
AMP + diphosphate
show the reaction diagram
5-phospho-alpha-D-ribose 1-diphosphate + guanine
GMP + diphosphate
show the reaction diagram
5-phospho-alpha-D-ribose 1-diphosphate + hypoxanthine
IMP + diphosphate
show the reaction diagram
5-phospho-alpha-D-ribose 1-diphosphate + xanthine
9-(5-phospho-beta-D-ribosyl)xanthine + diphosphate
show the reaction diagram
9-(5-phospho-beta-D-ribosyl)xanthine + diphosphate
5-phospho-alpha-D-ribose 1-diphosphate + xanthine
show the reaction diagram
-
-
-
-
?
IMP + diphosphate
5-phospho-alpha-D-ribose 1-diphosphate + hypoxanthine
show the reaction diagram
-
-
-
-
r
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
5-phospho-alpha-D-ribose 1-diphosphate + xanthine
9-(5-phospho-beta-D-ribosyl)xanthine + diphosphate
show the reaction diagram
-
the enzyme is involved in purine nucleotide synthesis via phosphorylation of purines acquisited from the host, since Leishmania donovani is not able to perform de novo biosynthesis of purine nucleotides
-
-
?
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-Methylxanthine
-
-
2,4-dihydroxy-5,6-tetramethylenepyrimidine
-
-
2,4-Dihydroxypteridine
-
-
2,4-dihydroxypyrido[2,3-d]pyrimidine
-
-
2,4-dihydroxypyrido[3,2-d]pyrimidine
-
-
2,4-dihydroxypyrido[3,4-d]pyrimidine
-
-
2,4-dihydroxypyrrolo[2,3-d]pyrimidine
-
-
2,6-Diaminopurine
-
-
2,6-dichloropurine
-
-
2,6-dioxo-1,3,7-trimethylpurine
-
-
2,6-dioxo-1,3,9-trimethylpurine
-
-
2,6-dioxo-3-isobutyl-1-methylpurine
-
-
2,6-dioxo-7-(beta-hydroxypropyl)-1,3-dimethylpurine
-
-
2,6-dithiopurine
-
-
2,6-dithioxanthine
-
-
2-amino-1-methylhypoxanthine
-
-
2-amino-1-methylpurine
-
-
2-amino-6-chloropurine
-
-
2-amino-7-deazahypoxanthine
-
-
2-amino-7-methylhypoxanthine
-
-
2-amino-9-deazahypoxanthine
-
-
2-amino-9-methylhypoxanthine
-
-
2-aminohypoxanthine
-
-
2-Aminopurine
-
-
2-aminopurine-6-thione
-
-
2-aza-3-deazahypoxanthine
-
-
2-aza-6-amino-3-deazapurine
-
-
2-aza-6-thio-3-deazapurine
-
-
2-hydroxy-6-methylthiopurine
-
-
2-Hydroxypurine
-
-
2-mercaptopurine
-
-
2-methylhypoxanthine
-
-
2-methylthio-6-hydroxypurine
-
-
-
2-oxo 7-methylhypoxanthine
-
-
2-oxo-1-methylhypoxanthine
-
-
2-oxo-3-methylhypoxanthine
-
-
2-oxo-6-thiopurine
-
-
2-oxohypoxanthine
-
-
2-oxohypoxanthine-N3-oxide
-
-
2-oxopurine
-
-
2-thiohypoxanthine
-
-
2-Thioxanthine
-
-
3-Methylxanthine
-
-
4,6-dihydroxypyrazolo[3,4-d]-pyrimidine
-
-
4-aminoimidazole-5-carboxamide
-
-
4-hydroxypyrazolo[3,4-d]pyrimidine
-
-
4-mercapto-6-hydroxypyrazolo[3,4-d]pyrimidine
-
-
4-mercaptopyrazolo[3,4-d]pyrimidine
-
-
4-oxopyrimidine
-
-
5(4)-amino-4-imidazolecarboxamide
-
-
-
5,7-dihydroxy(1,2,5)thiadiazolo[3,4-d]pyrimidine
-
-
5,7-dihydroxy-v-triazolo[4,5-d]pyrimidine
-
-
5,7-dihydroxypyrazolo[4,3-d]pyrimidine
-
-
5-acetamidouracil
-
-
5-Aminouracil
-
-
5-anilinouracil
-
-
5-fluorocytosine
-
-
5-formamidouracil
-
-
5-phospho-alpha-D-ribose 1-diphosphate
-
-
6-amino-1-methylpurine
-
-
6-amino-2,8-diaza-3-deazapurine
-
-
6-amino-2-chloropurine
-
-
6-amino-2-methylpurine
-
-
6-amino-2-oxopurine
-
-
6-amino-7-deazapurine
-
-
6-amino-8-bromopurine
-
-
6-benzylaminopurine
-
-
6-Chloropurine
-
-
6-Hydroxymethylpterin
-
-
6-Mercaptopurine
-
-
6-methoxypurine
-
-
6-Methylaminopurine
-
-
6-Thiopurine
-
-
6-Thioxanthine
-
-
7-methylxanthine
-
-
8-aza-1,3-dideazapurine
-
-
8-aza-1-nitro-1,3-dideazapurine
-
-
8-aza-2,6-diaminopurine
-
-
8-aza-2-aminohypoxanthine
-
-
8-aza-6-aminopurine
-
-
8-aza-7-deaza-6-aminopurine
-
-
8-aza-7-deaza-6-thiopurine
-
-
8-aza-7-deazahypoxanthine
-
-
8-Azahypoxanthine
-
-
8-bromo-2-aminohypoxanthine
-
-
8-mercaptoxanthine
-
-
8-methylxanthine
-
-
8-oxohypoxanthine
-
-
8-thiohypoxanthine
-
-
9-methylxanthine
-
-
adenine
ATP
-
1 mM, 11% inhibition
Benzonitrile
-
-
CDP
-
1 mM, 10% inhibition
CTP
-
1 mM, 27% inhibition
cytosine
-
-
GDP
-
1 mM, 93 inhibition
GTP
-
1 mM, 91% inhibition
Guanine
hypoxanthine
isocytosine
-
-
isoguanine
-
-
Pyrophosphate
noncompetitive
TDP
-
1 mM, 18% inhibition
TTP
-
1 mM, 13% inhibition
UDP
-
1 mM, 15% inhibition
Uracil
UTP
-
1 mM, 17% inhibition
xanthine
XDP
-
1 mM, 89% inhibition
XTP
-
1 mM, 92% inhibition
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.019
5,7-dihydroxy-v-triazolo[4,5-d]pyrimidine
-
-
0.0034 - 0.139
5-phospho-alpha-D-ribose 1-diphosphate
0.092 - 0.533
9-(5-phospho-beta-D-ribosyl)xanthine
0.0029
adenine
-
-
0.0059 - 0.133
diphosphate
0.0013 - 0.281
Guanine
0.0012 - 1.25
hypoxanthine
0.0078 - 0.008
IMP
0.001 - 0.0913
xanthine
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.1 - 112
5-phospho-alpha-D-ribose 1-diphosphate
0.00367 - 0.043
9-(5-phospho-beta-D-ribosyl)xanthine
0.0038 - 0.025
diphosphate
0.03 - 112
Guanine
0.5 - 54.8
hypoxanthine
0.006167
IMP
Leishmania donovani
-
mutant E198D/E215D, at 25C, in TM buffer
2 - 150
xanthine
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.024
2,4-Dihydroxypteridine
-
-
0.0041
2,4-dihydroxypyrido[3,2-d]pyrimidine
-
-
0.41
2,6-dichloropurine
-
-
1.5
2,6-dioxo 3-isobutyl-1-methylpurine
-
-
1
2,6-dioxo-1,3,7-trimethylpurine
-
-
5.3
2,6-dioxo-1,3,9-trimethylpurine
-
-
1.9
2,6-dioxo-7-(beta-hydroxypropyl)-1,3-dimethylpurine
-
-
0.42
2,6-dithiopurine
-
-
0.15
2,6-dithioxanthine
-
-
0.04
2-amino 1-methylhypoxanthine
-
-
0.29
2-amino 1-methylpurine
-
-
0.23
2-amino-6-chloropurine
-
-
0.026
2-amino-7-deazahypoxanthine
-
-
3.1
2-amino-7-methylhypoxanthine
-
-
0.014
2-amino-9-deazahypoxanthine
-
-
0.23
2-amino-9-methylhypoxanthine
-
-
0.012
2-aminohypoxanthine
-
-
0.067
2-Aminopurine
-
-
0.002
2-aminopurine-6-thione
-
-
0.022
2-aza-3-deazahypoxanthine
-
-
0.231
2-aza-6-amino-3-deazapurine
-
-
0.03
2-aza-6-thio-3-deazapurine
-
-
0.17
2-hydroxy-6-methylthiopurine
-
-
1.4
2-oxo 1-methylhypoxanthine
-
-
1.9
2-oxo 7-methylhypoxanthine
-
-
0.246
2-oxo-6-thiopurine
-
-
0.014
2-oxohypoxanthine
-
-
1.3
2-oxohypoxanthine-N3-oxide
-
-
0.57
2-oxopurine
-
-
0.068
2-thiohypoxanthine
-
-
0.38
2-Thioxanthine
-
-
0.62
3-Methylxanthine
-
-
0.31
4,6-dihydroxypyrazolo[3,4-d]-pyrimidine
-
-
0.2
4-mercapto-6-hydroxypyrazolo[3,4-d]pyrimidine
-
-
0.379
4-oxopyrimidine
-
-
0.0079
5(4)-amino-4-imidazolecarboxamide
-
-
-
0.032
5,7-dihydroxy(1,2,5)thiadiazolo[3,4-d]pyrimidine
-
-
0.11
5,7-dihydroxy-v-triazolo[4,5-d]pyrimidine
-
-
0.0022
5,7-dihydroxypyrazolo[4,3-d]pyrimidine
-
-
0.657
5-fluorocytosine
-
-
0.021
5-phospho-alpha-D-ribose 1-diphosphate
-
-
0.31
6-amino 1-methylpurine
-
-
0.437
6-amino-2,8-diaza-3-deazapurine
-
-
2.2
6-amino-2-chloropurine
-
-
0.37
6-amino-2-methylpurine
-
-
0.053
6-amino-2-oxopurine
-
-
1.7
6-amino-7-deazapurine
-
-
0.75
6-amino-8-bromopurine
-
-
1.1
6-benzylaminopurine
-
-
0.1
6-Chloropurine
-
-
3.4
6-Hydroxymethylpterin
-
-
0.38
6-methoxypurine
-
-
0.97
6-Methylaminopurine
-
-
0.006
6-Thiopurine
-
-
0.34
6-Thioxanthine
-
-
5.2
8-aza-1,3-dideazapurine
-
-
0.39
8-aza-1-nitro-1,3-dideazapurine
-
-
0.85
8-aza-2,6-diaminopurine
-
-
2.6
8-aza-2-aminohypoxanthine
-
-
2.5
8-aza-6-aminopurine
-
-
0.88
8-aza-7-deaza 6-thiopurine
-
-
0.081
8-aza-7-deaza-6-aminopurine
-
-
0.035
8-aza-7-deazahypoxanthine
-
-
2
8-Azahypoxanthine
-
-
0.54
8-bromo-2-aminohypoxanthine
-
-
0.39
8-mercaptoxanthine
-
-
4.1
8-oxohypoxanthine
-
-
0.42
8-thiohypoxanthine
-
-
0.87
Benzonitrile
-
-
0.286
cytosine
-
-
0.033 - 0.067
GMP
0.1
Guanine
-
-
0.0035
hypoxanthine
-
-
1.06
isocytosine
-
-
0.808
Uracil
-
-
0.024
xanthine
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
-
reaction with hypoxanthine and guanine
7.8
-
reaction with xanthine
8 - 8.5
substrate: xanthine
8 - 9.5
-
reaction with adenine
9.5
substrate: hypoxanthine
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.9 - 9.1
-
80% of maximal activity at pH 6.9 and 9.1
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
deletion of the glycosomal targeting sequence, a C-terminal tripeptide, leads to mislocation of the enzyme in the cytosol, where the enzyme nevertheless is still active
Manually annotated by BRENDA team
-
deletion of the peroxisomal targeting sequence is not required for activity
Manually annotated by BRENDA team
additional information
-
immunohistologic subcellular localization study
-
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
UNIPROT
Bacillus subtilis (strain 168)
Bacillus subtilis (strain 168)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
27000
-
gel filtration
42000
-
gel filtration
54000
-
in absence of 5-phospho-alpha-D-ribose 1-diphosphate, gel filtration
62000
-
in presence of 5-phospho-alpha-D-ribose 1-diphosphate, gel filtration
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
crystal structure of the dimeric XPRTase-GMP complex was determined to 2.05 A resolution
hanging drop vapor diffusion method
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.6 - 10
-
stable
638005
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
-
pH 5.6-10, stable for 30 min
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
increase in potassium phosphate buffer concentration from 1-50 mM increases stability
-
stabilizing compounds are: 5-phospho-alpha-D-ribose 1-diphosphate, XMP, 6-oxo-substituted purine nucleotides
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70C, stable for 6 months in intacts cells
-
-80C, 10 mM Tris-HCl buffer, pH 7.5
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
by gel filtration, more than 95% pure
-
purification and formation of nucleotide free, GMP and XMP saturated complexes
recombinant full length and C-terminally truncated enzymes from Escherichia coli by affinity chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Escherichia coli Sphi606 or Sphi609 cells transformed with pSelect-LdXPRT, pSelectldxprtE198D, pSelect-ldxprtE215D, pSelect-ldxprtE215Q and pSelectldxprtE198,215D
-
expression in Escherichia coli
-
expression of full length and C-terminally truncated enzymes in Escherichia coli
-
isolation and characterization of the XPT1 gene
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
E198D
-
increases the turnover rates of the xanthine phosphoribosyltransferase without altering purine nucleobase specificity, converts the xanthine phosphoribosyltransferase into a broad-specificity enzyme capable of utilizing guanine, hypoxanthine, and xanthine as substrates. Can accommodate GMP in the active site
E198D/E215D
-
catalyzes robust guanine phosphoribosylation. Exhibits similar kinetic parameters in the presence of Mg2+ or Mn2+ as the wild-type. Substitution of Mg2+ with Mn2+ does not alter the hypoxanthine phosphoribosylation activity
E215D
-
increases the turnover rates of the xanthine phosphoribosyltransferase without altering purine nucleobase specificity, converts the xanthine phosphoribosyltransferase into a broad-specificity enzyme capable of utilizing guanine, hypoxanthine, and xanthine as substrates. Can accommodate GMP in the active site
E215Q
-
can accommodate GMP in the active site
additional information
-
deletion of the glycosomal targeting sequence, a C-terminal tripeptide, leads to mislocation of the enzyme in the cytosol, where the enzyme nevertheless is still active
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
-
the enzyme lacks a mammalian counterpart and is, therefore, a potential target for antiparasitic therapy
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