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EC Tree
IUBMB Comments Requires iron(II) for activity. Unlike the proline hydroxylases involved in collagen biosynthesis [EC 1.14.11.2 (procollagen-proline dioxygenase) and EC 1.14.11.7 (procollagen-proline 3-dioxygenase)], this enzyme does not require ascorbate for activity although it does increase the activity of the enzyme . The enzyme is specific for L-proline as D-proline, trans-4-hydroxy-L-proline, cis-4-hydroxy-L-proline and 3,4-dehydro-DL-proline are not substrates .
Word Map
1.14.11.28
2-oxoglutarate-dependent
leprel1
early-onset
ferrous
myopia
exome
autosomal-recessive
choroid
neovascularization
3-hydroxyproline
regio
pharmacology
4-hydroxylase
cataract
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
proline 3-hydroxylase, c-p3h,
more
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collagen prolyl hydroxylases 3
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collagen prolyl hydroxylases 4
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proline 3-hydroxylase type I
proline 3-hydroxylase type II
prolyl 3-hydroxylase 2
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L-proline-3-hydroxylase
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L-proline-3-hydroxylase
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Leprel1
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P-3-H
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P3H
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P3H2
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proline 3-hydroxylase
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proline 3-hydroxylase
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proline 3-hydroxylase
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proline 3-hydroxylase
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proline 3-hydroxylase
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proline 3-hydroxylase
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proline 3-hydroxylase type I
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proline 3-hydroxylase type I
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proline 3-hydroxylase type II
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proline 3-hydroxylase type II
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-
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L-proline + 2-oxoglutarate + O2 = cis-3-hydroxy-L-proline + succinate + CO2
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-
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-
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L-proline,2-oxoglutarate:oxygen oxidoreductase (3-hydroxylating)
Requires iron(II) for activity. Unlike the proline hydroxylases involved in collagen biosynthesis [EC 1.14.11.2 (procollagen-proline dioxygenase) and EC 1.14.11.7 (procollagen-proline 3-dioxygenase)], this enzyme does not require ascorbate for activity although it does increase the activity of the enzyme [2]. The enzyme is specific for L-proline as D-proline, trans-4-hydroxy-L-proline, cis-4-hydroxy-L-proline and 3,4-dehydro-DL-proline are not substrates [2].
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3,4-dehydro-L-proline + 2-oxoglutarate + O2
cis-3,4-epoxy-L-proline + succinate + CO2
L-2-azetidinecarboxylic acid + 2-oxoglutarate + O2
cis-3-hydroxyazetidine-L-2-carboxylic acid + succinate + CO2
L-pipecolic acid + 2-oxoglutarate + O2
cis-3-hydroxy-L-pipecolic acid + succinate + CO2
L-proline + 2-oxoglutarate + O2
cis-3-hydroxy-L-proline + succinate + CO2
3,4-dehydro-L-proline + 2-oxoglutarate + O2
cis-3,4-epoxy-L-proline + succinate + CO2
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-
-
-
?
3,4-dehydro-L-proline + 2-oxoglutarate + O2
cis-3,4-epoxy-L-proline + succinate + CO2
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-
-
-
?
L-2-azetidinecarboxylic acid + 2-oxoglutarate + O2
cis-3-hydroxyazetidine-L-2-carboxylic acid + succinate + CO2
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?
L-2-azetidinecarboxylic acid + 2-oxoglutarate + O2
cis-3-hydroxyazetidine-L-2-carboxylic acid + succinate + CO2
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-
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?
L-pipecolic acid + 2-oxoglutarate + O2
cis-3-hydroxy-L-pipecolic acid + succinate + CO2
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-
-
-
?
L-pipecolic acid + 2-oxoglutarate + O2
cis-3-hydroxy-L-pipecolic acid + succinate + CO2
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-
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?
L-proline + 2-oxoglutarate + O2
cis-3-hydroxy-L-proline + succinate + CO2
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-
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?
L-proline + 2-oxoglutarate + O2
cis-3-hydroxy-L-proline + succinate + CO2
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-
-
-
?
L-proline + 2-oxoglutarate + O2
cis-3-hydroxy-L-proline + succinate + CO2
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?
L-proline + 2-oxoglutarate + O2
cis-3-hydroxy-L-proline + succinate + CO2
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-
-
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?
L-proline + 2-oxoglutarate + O2
cis-3-hydroxy-L-proline + succinate + CO2
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-
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?
L-proline + 2-oxoglutarate + O2
cis-3-hydroxy-L-proline + succinate + CO2
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product identification and analysis by NMR spectroscopy
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?
L-proline + 2-oxoglutarate + O2
cis-3-hydroxy-L-proline + succinate + CO2
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-
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?
L-proline + 2-oxoglutarate + O2
cis-3-hydroxy-L-proline + succinate + CO2
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product identification and analysis by NMR spectroscopy
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?
L-proline + 2-oxoglutarate + O2
cis-3-hydroxy-L-proline + succinate + CO2
-
-
-
-
?
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L-proline + 2-oxoglutarate + O2
cis-3-hydroxy-L-proline + succinate + CO2
L-proline + 2-oxoglutarate + O2
cis-3-hydroxy-L-proline + succinate + CO2
-
-
-
-
?
L-proline + 2-oxoglutarate + O2
cis-3-hydroxy-L-proline + succinate + CO2
-
-
-
-
?
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2-oxoglutarate
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strictly required
2-oxoglutarate
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strictly required, highest activity at 4 mM
2-oxoglutarate
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strictly required, highest activity at 4 mM
2-oxoglutarate
-
strictly required, highest activity at 4 mM
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Fe2+
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1 mM added to cell extracts, 60% inhibition without addition of Fe2+
Fe2+
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1 mM added to cell extracts, 85% inhibition without addition of Fe2+
Fe2+
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1 mM added to cell extracts, complete inhibition without addition of Fe2+
Fe2+
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activates, required
Fe2+
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1 mM added to cell extracts, 60% inhibition without addition of Fe2+
Fe2+
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strictly required, optimal stimulation at 1 mM
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Citric acid
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30% inhibition at 5 mM
CoCl2
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82% inhibition at 0.1 mM, 98% inhibition at 1 mM, 5 mM 2-oxoglutarate, 1 mM ferrous sulfate, 5 mM L-ascorbic acid, 100 mM TES pH 7.5, 30°C
CuSO4
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59% inhibition at 0.1 mM, complete inhibition at 1 mM, 5 mM 2-oxoglutarate, 1 mM ferrous sulfate, 5 mM L-ascorbic acid, 100 mM TES pH 7.5, 30°C
Ni2+
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more than 50% inhibition at 1 mM
ZnSO4
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95% inhibition at 0.1 mM, complete inhibition at 1 mM, 5 mM 2-oxoglutarate, 1 mM ferrous sulfate, 5 mM L-ascorbic acid, 100 mM TES pH 7.5, 30°C
Co2+
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more than 50% inhibition at 1 mM
Co2+
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more than 90% inhibition at 1 mM
Cu2+
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more than 50% inhibition at 1 mM
Cu2+
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more than 90% inhibition at 1 mM
EDTA
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95% inhibition at 2 mM, 5 mM 2-oxoglutarate, 1 mM ferrous sulfate, 5 mM L-ascorbic acid, 100 mM TES pH 7.5, 30°C
EDTA
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more than 50% inhibition at 1 mM
EDTA
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95% inhibition at 2 mM
Zn2+
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more than 50% inhibition at 1 mM
Zn2+
-
more than 90% inhibition at 1 mM
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L-ascorbate
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2 mM, no further stimulation above 2 mM
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Lymphoma
The collagen prolyl hydroxylases are novel transcriptionally silenced genes in lymphoma.
Neoplasms
The collagen prolyl hydroxylases are novel transcriptionally silenced genes in lymphoma.
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0.047 - 0.11
2-oxoglutarate
8.4
3,4-dehydro-L-proline
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-
2.1
L-2-azetidinecarboxylic acid
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3.8 - 100
L-pipecolic acid
0.047
2-oxoglutarate
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0.11
2-oxoglutarate
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100 mM N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid pH 7.0, 5 mM 2-oxoglutarate, 5 mM L-proline, 5 mM L-ascorbate, 1 mM FeSO4, 35°C
3.8
L-pipecolic acid
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0.2
L-proline
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0.56
L-proline
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100 mM N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid pH 7.0, 5 mM 2-oxoglutarate, 5 mM L-proline, 5 mM L-ascorbate, 1 mM FeSO4, 35°C
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3.2
L-proline
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100 mM N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid pH 7.0, 5 mM 2-oxoglutarate, 5 mM L-proline, 5 mM L-ascorbate, 1 mM FeSO4, 35°C
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0.00119
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5 mM 2-oxoglutarate, 1 mM ferrous sulfate, 5 mM L-ascorbic acid, 100 mM TES pH 7.5, 30°C
additional information
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recombinant biotransformation of L-proline to cis-3-hydroxy-L-proline in Escherichia coli cells transformed with a synthetic P3H gene, overview
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brenda
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brenda
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brenda
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brenda
strain ATCC 12647
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brenda
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brenda
P3H2
UniProt
brenda
P3H3
UniProt
brenda
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-
-
brenda
strainTH1
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brenda
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brenda
strainTH1
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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physiological function
P3H2 can function as a tumour suppressors in breast cancer
physiological function
P3H3 can function as a tumour suppressors in breast cancer
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P3H1_STRSQ
Streptomyces sp
290
0
33154
Swiss-Prot
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P3H2_STRSQ
Streptomyces sp
290
0
33574
Swiss-Prot
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A0A100J7I3_9ACTN
278
0
30543
TrEMBL
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A0A160FB59_9BACI
205
0
24102
TrEMBL
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A0A6J5ECD5_9BURK
298
0
34941
TrEMBL
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A0A6J5DDW6_9BURK
320
0
37242
TrEMBL
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A0A160FAZ8_9BACI
69
0
8359
TrEMBL
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A0A0F5RIE2_9BACI
296
0
35107
TrEMBL
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A0A7L4ZI96_9FLAO
198
0
22573
TrEMBL
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P3H1_HUMAN
736
0
83394
Swiss-Prot
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P3H3_HUMAN
736
0
81837
Swiss-Prot
-
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33154
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x * 33154, sequence calculation
35000
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SDS-PAGE
35000
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apparent molecular weight on SDS-PAGE
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?
-
x * 33154, sequence calculation
?
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x * 33154, sequence calculation
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dimer
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X-ray structure
dimer
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X-ray structure
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G508V
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mutation is associated with high myopia in human. Mutant G508V expressed in insect cells is completely inactive
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5.5 - 8.5
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activity remained above 85% after 16 h at 4°C
664403
5.5 - 9
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activity remained above 85% after 16 h at 4°C
664403
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30
-
below 30°C activity remained above 85% after 30 min at pH 6.0
40
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below 40°C activity remained above 85% after 30 min at pH 6.0
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2 chromatographic steps to homogeneity
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5 chromatographic steps near to homogeneity
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expression in Escherichia coli
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gene P3H, DNA and amino acid sequence determination and analysis, preparation of a synthetic gene encoding proline 3-hydroxylase and cloning and overexpression of proline 3-hydroxylase protein in Escherichia coli strain BL21(DE3) resulting in strain SC16497, biotransformation rates, overview
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C-P3H is downregulated in lymphoma. Down-regulation is associated with methylation in the CpG islands and is detected in almost all common types of B-cell lymphoma
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C-P4H is downregulated in lymphoma. Down-regulation is associated with methylation in the CpG islands and is detected in almost all common types of B-cell lymphoma
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the enzyme expression of P3H2 and P3H3 is downregulated in breast cancer by abberrant CpG methylation in the 5'-regulatory sequences of each gene, methylation of P3H3 is not associated with higher tumour grade and Nottingham prognostic index
the enzyme expression of P3H2 is downregulated in breast cancer by abberrant CpG methylation in the 5'-regulatory sequences of each gene, methylation of P3H2 is specific for breast cancer and does not occur in other cancer cell types, it is strongly associated with higher tumour grade and Nottingham prognostic index
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pharmacology
the prolyl 3-hydroxylase P3H2 is a novel targets for epigenetic silencing in breast cancer
pharmacology
the prolyl 3-hydroxylase P3H3 is a novel targets for epigenetic silencing in breast cancer
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Mori, H.; Shibasaki, T.; Uozaki, Y.; Ochiai, K.; Ozaki, A.
Detection of novel proline 3-hydroxylase activities in Streptomyces and Bacillus spp. by regio- and stereospecific hydroxylation of L-proline
Appl. Environ. Microbiol.
62
1903-1907
1996
Bacillus sp. (in: Bacteria), Streptomyces sp., Streptomyces canus, Bacillus sp. (in: Bacteria) TH2, Bacillus sp. (in: Bacteria) TH3, Streptomyces sp. TH1
brenda
Shibasaki, T.; Mori, H.; Ozaki, A.
Cloning of an isozyme of proline 3-hydroxylase and its purification from recombinant Escherichia coli
Biotechnol. Lett.
22
1967-1973
2000
Streptomyces sp., Streptomyces sp. TH1
-
brenda
Clifton, I.J.; Hsueh, L.C.; Baldwin, J.E.; Harlos, K.; Schofield, C.J.
Structure of proline 3-hydroxylase. Evolution of the family of 2-oxoglutarate dependent oxygenases
Eur. J. Biochem.
268
6625-6636
2001
Streptomyces sp., Streptomyces sp. TH1
brenda
Mori, H.; Shibasaki, T.; Yano, K.; Ozaki, A.
Purification and cloning of a proline 3-hydroxylase, a novel enzyme which hydroxylates free L-proline to cis-3-hydroxy-L-proline
J. Bacteriol.
179
5677-5683
1997
Streptomyces sp., Streptomyces sp. TH1
brenda
Vranka, J.A.; Sakai, L.Y.; Bachinger, H.P.
Prolyl 3-hydroxylase 1, enzyme characterization and identification of a novel family of enzymes
J. Biol. Chem.
279
23615-23621
2004
Gallus gallus
brenda
Shibasaki, T.; Sakurai, W.; Hasegawa, A.; Uosaki, Y.; Mori, H.; Yoshida, M.; Ozaki, A.
Substrate selectivities of proline hydroxylases
Tetrahedron Lett.
40
5227-5230
1999
Streptomyces sp., Streptomyces sp. TH1
-
brenda
Shah, R.; Smith, P.; Purdie, C.; Quinlan, P.; Baker, L.; Aman, P.; Thompson, A.M.; Crook, T.
The prolyl 3-hydroxylases P3H2 and P3H3 are novel targets for epigenetic silencing in breast cancer
Br. J. Cancer
100
1687-1696
2009
Homo sapiens (Q32P28), Homo sapiens (Q8IVL6)
brenda
Johnston, R.; Chu, L.; Liu, M.; Goldberg, S.; Goswami, A.; Patel, R.
Hydroxylation of L-proline to cis-3-hydroxy-L-proline by recombinant Escherichia coli expressing a synthetic L-proline-3-hydroxylase gene
Enzyme Microb. Technol.
45
484-490
2009
Streptomyces sp., Streptomyces sp. TH1
-
brenda
Mordechai, S.; Gradstein, L.; Pasanen, A.; Ofir, R.; El Amour, K.; Levy, J.; Belfair, N.; Lifshitz, T.; Joshua, S.; Narkis, G.; Elbedour, K.; Myllyharju, J.; Birk, O.S.
High myopia caused by a mutation in LEPREL1, encoding prolyl 3-hydroxylase 2
Am. J. Hum. Genet.
89
438-445
2011
Homo sapiens
brenda
Hatzimichael, E.; Lo Nigro, C.; Lattanzio, L.; Syed, N.; Shah, R.; Dasoula, A.; Janczar, K.; Vivenza, D.; Monteverde, M.; Merlano, M.; Papoudou-Bai, A.; Bai, M.; Schmid, P.; Stebbing, J.; Bower, M.; Dyer, M.J.; Karran, L.E.; ElguetaKarstegl, C.; Farrell, P.J.; Thompson, A.; Briasoulis, E.; Crook, T.
The collagen prolyl hydroxylases are novel transcriptionally silenced genes in lymphoma
Br. J. Cancer
107
1423-1432
2012
Homo sapiens
brenda
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