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Information on EC 5.3.2.1 - phenylpyruvate tautomerase and Organism(s) Mus musculus and UniProt Accession P34884
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5.3.2.1 phenylpyruvate tautomeraseIUBMB Comments
Also acts on other arylpyruvates.
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Word Map
- 5.3.2.1
- necrosis
- monocyte
- tnf
- endothelial
- lymphocyte
- chemokine
- autoimmune
-
anti-mif
- glucocorticoid
- arthritis
- pulmonary
- artery
- leukocyte
- angiogenesis
- sepsis
-
rheumatoid
- tnf-alpha
- lipopolysaccharide
- factor-alpha
- myocardial
- t-cells
- atherosclerosis
-
chemotactic
-
c-reactive
- pituitary
-
chemoattractant
- infarct
-
lupus
- lymphokine
-
toll-like
-
autocrine
- cxcr2
-
synovial
- ifn-gamma
- il-1beta
-
counter-regulator
-
chemokine-like
- erythematosus
-
immunoregulatory
-
cell-mediated
- glomerulonephritis
-
dehalogenation
-
tautomerization
-
counterregulates
-
delayed-type
-
pro-tumorigenic
- drug development
The taxonomic range for the selected organisms is: Mus musculus
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
macrophage migration inhibitory factor, cis-caad, mif tautomerase, trans-3-chloroacrylic acid dehalogenase, cis-3-chloroacrylic acid dehalogenase, phenylpyruvate tautomerase, phenylpyruvate keto-enol tautomerase, macrophage migration inhibitory factor tautomerase, 
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topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Macrophage migration inhibitory factor
MIF
Phenylpyruvate keto-enol tautomerase
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-
-
-
Phenylpyruvic keto-enol isomerase
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-
-
-
Tautomerase, phenylpyruvate
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-
-
-
Macrophage migration inhibitory factor
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-
-
-
MIF
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
isomerization
-
-
-
-
intramolecular oxidoreduction
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-
-
-
tautomerization
-
-
-
-
PATHWAY SOURCE
PATHWAYS
SYSTEMATIC NAME
IUBMB Comments
phenylpyruvate keto---enol-isomerase
Also acts on other arylpyruvates.
CAS REGISTRY NUMBER
COMMENTARY
9023-54-5
-
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
4-(hydroxyphenyl)pyruvate
4-(hydroxyphenyl)pyruvate
enol form
keto form
-
?
enol-(p-hydroxyphenyl)pyruvate
keto-(p-hydroxyphenyl)pyruvate
-
-
r
keto-(p-hydroxyphenyl)pyruvate
enol-(p-hydroxyphenyl)pyruvate
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-
r
additional information
?
-
-
the enzymatic activity of macrophage migration inhibitory factor does not play a role in its migration inhibiting properties. Macrophage migration inhibitory factor is an inhibitor of the random migration of monocytes and macrophages and has since been proposed to have a number of immune and catalytic functions, macrophage migration inhibitory factor is an inhibitor of monocyte chemoattractant protein 1-induced chemotaxis of human peripheral blood monocytes
-
?
enol-phenylpyruvate
keto-phenylpyruvate
-
-
reaction is stereoselective, generating the (3R) isomer of [3-D]phenylpyruvate in D2O in a ratio of 6.6:1
-
?
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
additional information
?
-
-
the enzymatic activity of macrophage migration inhibitory factor does not play a role in its migration inhibiting properties. Macrophage migration inhibitory factor is an inhibitor of the random migration of monocytes and macrophages and has since been proposed to have a number of immune and catalytic functions, macrophage migration inhibitory factor is an inhibitor of monocyte chemoattractant protein 1-induced chemotaxis of human peripheral blood monocytes
-
?
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2-oxo-4-phenyl-3-butynoate
irreversible inactivation by covalent modifiaction of N-terminal proline residue via a Michael-addition of proline to C4 of the inhibitor
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
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). MIF_MOUSE
115
0
12504
Swiss-Prot
other Location (Reliability: 2)
PDB
SCOP
CATH
UNIPROT
ORGANISM
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
12335
x * 12335, electrospray ionization mass spectrometry, mutant enzyme P1G
12347
12358
x * 12358, electrospray ionization mass spectrometry, mutant enzyme Y95F
12371
x * 12371, electrospray ionization mass spectrometry, wild-type enzyme
12316
-
x * 12316, mutant enzyme K32A, electrospray ionization mass spectrometry
12401
-
x * 12401, mutant enzyme K32R, electrospray ionization mass spectrometry
12347
x * 12347, electrospray ionization mass spectrometry, mutant enzyme N97A
12347
x * 12347, electrospray ionization mass spectrometry, mutant enzyme P1A
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
x * 12335, electrospray ionization mass spectrometry, mutant enzyme P1G
?
x * 12347, electrospray ionization mass spectrometry, mutant enzyme N97A
?
x * 12347, electrospray ionization mass spectrometry, mutant enzyme P1A
?
x * 12358, electrospray ionization mass spectrometry, mutant enzyme Y95F
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
crystal structure of a complex between enzyme and the competitive inhibitor (E)-2-fluoro-o-hydroxycinnamate determined to 1.8 A resolution
crystallization of the Y95F mutant enzyme by hanging drop vapor diffusion method, crystal structure of the enzyme with the competitive inhibitor (E)-2-fluoro-p-hydroxycinnamate bound at the active site and that of the protein complexed with the enol form of (p-hydroxyphenyl)pyruvate
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
N97A
the ratio of turnover number to Km-value for enol-phenylpyruvate is 21.3fold higher than that of the wild-type enzyme, the ratio of turnover number to Km-value for enol-(p-hydroxyphenyl)pyruvate is 1.5fold lower than that of the wild-type enzyme, 5fold increase in Ki-value for (E)-2-fluoro-p-hydroxycinnamate compared to the wild-type enzyme
P1A
the ratio of turnover number to Km-value for enol-phenylpyruvate is 232fold lower than that of the wild-type enzyme, the ratio of turnover number to Km-value for enol-(p-hydroxyphenyl)pyruvate is 114fold lower than that of the wild-type enzyme
P1G
the ratio of turnover number to Km-value for enol-phenylpyruvate is 232fold lower than that of the wild-type enzyme, the ratio of turnover number to Km-value for enol-(p-hydroxyphenyl)pyruvate is 143fold lower than that of the wild-type enzyme
Y95F
the ratio of turnover number to Km-value for enol-phenylpyruvate is 1.3fold lower than that of the wild-type enzyme, the ratio of turnover number to Km-value for enol-(p-hydroxyphenyl)pyruvate is 1.5fold higher than that of the wild-type enzyme
K32A
-
15fold decrease in Ki-value for the competitive inhibitor, (E)-2-fluoro-p-hydroxycinnamate compared to wild-type enzyme, turnover number for enol-phenylpyruvate is 9% of that for the wild-type enzyme, turnover number for enol-(p-hydroxyphenyl)pyruvate is 11% of that for the wild-type enzyme, the ratio of turnover number and Km-value for enol-phenylpyruvate is 8% of that for the wild-type enzyme, the ratio of turnover number and KM-value for enol(p-hydroxyphenyl)pyruvate is 16% of the value for the wild-type enzyme
K32R
-
modest decrease in the stereoselectivity of the reaction and in the binding affinity of the competitive inhibitor, (E)-2-fluoro-p-hydroxycinnamate, turnover number for enol-phenylpyruvate is 47% of that for the wild-type enzyme, turnover number for enol-(p-hydroxyphenyl)pyruvate is 110% of that for the wild-type enzyme, the ratio of turnover number and Km-value for enol-phenylpyruvate or enol(p-hydroxyphenyl)pyruvate is about 70% of the value for the wild-type enzyme
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
wild-type and mutant enzymes P1G, P1A, Y95F and N97A, expression in Escherichia coli BL21
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Hermanowski-Vosatka, A.; Mundt, S.S.; Ayala, J.M.; Goyal, S.; Hanlon, W.A.; Czerwinski, R.M.; Wright, S.D.; Whitman, C.P.
Enzymatically inactive macrophage migration inhibitory factor inhibits monocyte chemotaxis and random migration
Biochemistry
38
12841-12849
1999
Mus musculus
Johnson, W.H., Jr.; Czerwinski, R.M.; Stamps, S.L.; Whitman, C.P.
A kinetic and stereochemical investigation of the role of lysine-32 in the phenylpyruvate tautomerase activity catalyzed by macrophage migration inhibitory factor
Biochemistry
38
16024-16033
1999
Mus musculus
Taylor, A.B.; Johnson, W.H., Jr.; Czerwinski, R.M.; Li, H.S.; Hackert, M.L.; Whitman, C.P.
Crystal structure of macrophage migration inhibitory factor complexed with (E)-2-fluoro-p-hydroxycinnamate at 1.8 A resolution: implications for enzymatic catalysis and inhibition
Biochemistry
38
7444-7452
1999
Mus musculus (P34884), Mus musculus
Stamps, S.L.; Taylor, A.B.; Wang, S.C.; Hackert, M.L.; Whitman, C.P.
Mechanism of the phenylpyruvate tautomerase activity of macrophage migration inhibitory factor: properties of the P1G, P1A, Y95F, and N97A mutants
Biochemistry
39
9671-9678
2000
Mus musculus (P34884)
Poelarends, G.J.; Johnson, W.H.; Serrano, H.; Whitman, C.P.
Phenylpyruvate tautomerase activity of trans-3-chloroacrylic acid dehalogenase: evidence for an enol intermediate in the dehalogenase reaction?
Biochemistry
46
9596-9604
2007
Mus musculus, Pseudomonas pavonaceae, Pseudomonas pavonaceae 170
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