Information on EC 5.3.1.1 - Triose-phosphate isomerase

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

EC NUMBER
COMMENTARY hide
5.3.1.1
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RECOMMENDED NAME
GeneOntology No.
Triose-phosphate isomerase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
D-Glyceraldehyde 3-phosphate = glycerone phosphate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
intramolecular oxidoreduction
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isomerization
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of antibiotics
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Biosynthesis of secondary metabolites
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Calvin-Benson-Bassham cycle
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Carbon fixation in photosynthetic organisms
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formaldehyde assimilation III (dihydroxyacetone cycle)
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Fructose and mannose metabolism
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gluconeogenesis I
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gluconeogenesis II (Methanobacterium thermoautotrophicum)
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gluconeogenesis III
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glycerol degradation to butanol
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glycolysis
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Glycolysis / Gluconeogenesis
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glycolysis I (from glucose 6-phosphate)
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glycolysis II (from fructose 6-phosphate)
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glycolysis III (from glucose)
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glycolysis IV (plant cytosol)
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glycolysis V (Pyrococcus)
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Inositol phosphate metabolism
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Metabolic pathways
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Microbial metabolism in diverse environments
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photosynthesis
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sucrose degradation V (sucrose alpha-glucosidase)
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SYSTEMATIC NAME
IUBMB Comments
D-glyceraldehyde-3-phosphate aldose-ketose-isomerase
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CAS REGISTRY NUMBER
COMMENTARY hide
9023-78-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
gene tpi
UniProt
Manually annotated by BRENDA team
strain DSM319
SwissProt
Manually annotated by BRENDA team
strain DSM319
SwissProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
ssp. Lactis IL403. Enzyme is present in high excess in wild-type cells. 10% residual activity still support more than 70% of the wild-type glycolytic flux. At at residual triosephosphate isomerase activity of 3%, dihydroxyacetone phosphate level increases four times and coincides with an increase in formate production
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
strain RN4220
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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TIM deficiency is the only human glycolytic deficiency disease which is lethal, usually in early childhood. The disease symptoms concern hemolytic anemia but also neurological disorders
metabolism
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
D-glyceraldehyde 3-phosphate
dihydroxyacetone 3- phosphate
show the reaction diagram
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-
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r
D-glyceraldehyde 3-phosphate
dihydroxyacetone phosphate
show the reaction diagram
D-Glyceraldehyde 3-phosphate
Glycerone phosphate
show the reaction diagram
dihydroxyacetone 3-phosphate
D-glyceraldehyde 3-phosphate
show the reaction diagram
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-
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r
dihydroxyacetone phosphate
D-glyceraldehyde 3-phosphate
show the reaction diagram
glycerone phosphate
D-glyceraldehyde 3-phosphate
show the reaction diagram
glycerone phosphate
methylglyoxal + phosphate
show the reaction diagram
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-
-
?
glycolaldehyde
?
show the reaction diagram
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
D-glyceraldehyde 3-phosphate
dihydroxyacetone 3- phosphate
show the reaction diagram
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-
-
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r
D-glyceraldehyde 3-phosphate
dihydroxyacetone phosphate
show the reaction diagram
D-Glyceraldehyde 3-phosphate
Glycerone phosphate
show the reaction diagram
dihydroxyacetone 3-phosphate
D-glyceraldehyde 3-phosphate
show the reaction diagram
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-
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r
dihydroxyacetone phosphate
D-glyceraldehyde 3-phosphate
show the reaction diagram
additional information
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
no metal cations are required
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1Z,2Z)-N,N'-dihydroxy-4-methylcyclohexa-3,5-diene-1,2-diimine
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(2E)-2-[(4-methyl-5-oxido-1,2,5-oxadiazol-3-yl)methylidene]hydrazinecarbothioamide
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(2E)-2-[(5-nitrofuran-2-yl)methylidene]hydrazinecarbothioamide
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irreversible inhibitor
(2E)-2-[2-[(3-oxido-2,1,3-benzoxadiazol-5-yl)methoxy]benzylidene]-N-(prop-2-en-1-yl)hydrazinecarbothioamide
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irreversible inhibitor
(2E)-N-(naphthalen-2-yl)-2-[(2E)-3-(5-nitrofuran-2-yl)prop-2-en-1-ylidene]hydrazinecarboxamide
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irreversible inhibitor
(2E)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-[(5-nitrofuran-2-yl)methylidene]hydrazinecarboxamide
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irreversible inhibitor
(4-methyl-1,2,3-thiadiazol-5-yl)methanol
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29% inhibition at 0.4 mM
1,2,4-thiadiazole
1,2,6-thiadiazine
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irreversible inhibitor
1,3,4-oxathiazole
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1-Chloro-3-hydroxyacetone
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2,2'-methylenebis(1,3-benzothiazole)
2,4-Dinitrofluorobenzene
2,6-dibenzyl-4-[(5-nitrothiophen-2-yl)methylidene]-1,2,6-thiadiazinane-3,5-dione 1,1-dioxide
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irreversible inhibitor
2,9-dimethyl-beta-carbolinium ion
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2-(N-formyl-N-hydroxy)-aminoethyl phosphonate
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2-carboxyethyl methanethiosulfonate
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modifies four Cys per subunit of dimeric protein and induces 97% of inactivation. Inactivation does not affect secondary structure nor induce dimer dissociation. Cys modification decreases thermal stability of the enzyme
2-carboxyethylphosphonic acid
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2-methyl-beta-carbolinium ion
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2-phenyl-4H-chromen-4-one
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2-phosphoglycerate
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2-Phosphoglycolate
2-phosphoglycolic acid
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2-[(1E)-2-nitroprop-1-en-1-yl]thiophene
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2-[(3-aminophenyl)disulfanyl]aniline
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3,5-diphenyl-1,2,4-thiadiazole
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74% inhibition at 0.4 mM
3-(2-benzothiazolylthio)-1-propanesulfonic acid
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binds to the dimer interface of the enzyme and thereby abolishes its function with a high level of selectivity
3-(4-methylphenyl)-5-[(4-methylphenyl)sulfonyl]-1,2,4-thiadiazole
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3-nitrobiphenyl-4-amine
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3-phospho-D-glycerate
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3-phosphoglycerate
4,4'-Dithiopyridine
4-(4-nitrobenzylidene)-2,6-bis(2-phenylethyl)-1,2,6-thiadiazinane-3,5-dione 1,1-dioxide
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irreversible inhibitor, 85% inhibition at 0.4 mM
4-[(5-nitrofuran-2-yl)methylidene]-4H-1,2,6-thiadiazine-3,5-diamine 1,1-dioxide
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irreversible inhibitor
4-[(5-nitrothiophen-2-yl)methylidene]-2,6-bis(2-phenylethyl)-1,2,6-thiadiazinane-3,5-dione 1,1-dioxide
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irreversible inhibitor
5,5'-dithio-bis(2-nitrobenzoic acid)
5,5'-dithiobis(2-nitrobenzoate)
5-[(1E)-2-nitroprop-1-en-1-yl]-1,3-benzodioxole
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6,6'-bi-1,3-benzothiazole-2,2'-diamine
6-phosphogluconate
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5 mM, 9% inhibition
6-[(E)-2-(5-nitrothiophen-2-yl)ethenyl]-2,1,3-benzoxadiazole 1-oxide
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irreversible inhibitor
6-[(E)-2-[(4-fluorophenyl)sulfanyl]ethenyl]-2,1,3-benzoxadiazole 1-oxide
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irreversible inhibitor
8-bromo-5,10-dioxidophenazin-2-yl chloroacetate
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50% inhibition at 0.4 mM
Acetylphosphate
arsenate
AsO43-
Atrazine
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a herbicide which interferes with photosynthesis
bromohydroxyacetone phosphate
butylbrevifolin carboxylate
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Chloroacetol phosphate
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citrate
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25 mM, 9% inhibition
cyclo(Gly-Pro-Phe-Val-Phe-PSI[CS-NH]Phe)
cyclo[Trp-Phe-D-Pro-Phe-Phe-Lys(benzyloxycarbonyl)-]
cyclo[Trp-Tyr(OSO3Na)-D-Phe-Thr(OSO3Na)-Lys(benzyloxycarbonyl)-]
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noncompetitive, reversible
D-alpha-glycerophosphate
D-erythrose 4-phosphate
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DL-glycidol phosphate
ethyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,2,4-thiadiazole-5-carboxylate
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ethyl 3-phenyl-1,2,4-thiadiazole-5-carboxylate
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ethylbrevifolin carboxylate
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fluorodifen
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a herbicide which interferes with photosynthesis
fructose 1,6-diphosphate
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5 mM, 69% inhibition
fructose 6-phosphate
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5 mM, 44% inhibition
glucose 1-phosphate
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5 mM, 10% inhibition
glucose 6-phosphate
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5 mM, 25% inhibition
glycerol 1-phosphate
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GSSG
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oxidized glutathione is a strong inhibitor of the enzyme at low concentrations
H2O2
the inhibition of the enzyme is negligible when incubated with 0.1 mM H2O2, whereas a 10% inhibition is observed with 1 mM H2O2
iodoacetamide
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iodoacetate
KFGNGSYTGEVS
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peptide that corresponds to loop 3 of the triosephosphate isomerase, residues 68-79. Efficient inhibitor with the activity falling to about 45% at 1000fold molar excess of the peptide in case of the wild-type enzyme. In the case of either of the mutants, Y74C and Y74G, even at 100fold molar excess of the peptide, only 30% activity can be obtained
KYGNGSCTGEVS
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peptide that is an analog of the peptide that corresponds to loop 3 of the protein, residues 68-79, with the replacement Y74C and F69Y. Inhibits the activity of the mutant enzymes Y74C and Y74G, with about 40% activity remaining in the presence of 1000fold molar excess of the peptide
mannobiose
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Mannopentaose
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Mannotetraose
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Mannotriose
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docking simulation
methyl methanethiosulfonate
methylbrevifolin carboxylate
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molecular docking simulations and enzyme binding structure, and inhibition kinetics, overview
methylmethane thiosulfonate
N-ethylmaleimide
N-[(2-oxido-4-phenyl-1,2,5-oxadiazol-3-yl)methyl]naphthalen-1-amine
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72% inhibition at 0.4 mM
N-[(4-methyl-5-oxido-1,2,5-oxadiazol-3-yl)methyl]naphthalen-1-amine
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41% inhibition at 0.4 mM
o-Iodosobenzoate
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p-benzoquinone
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p-hydroxymercuribenzoate
phenazine 5,9-dioxide
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84% inhibition at 0.4 mM
phosphate
phosphoenolpyruvate
Phosphoglycolate
phosphoglycoloaldoxime
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phosphoglycolohydrazide
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Phosphoglycolohydroxamate
S-Phenyl-p-toluenethiosulfonate
succinate
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5 mM, 9% inhibition
suramin
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[3-amino-3-(hydroxyimino)propyl]phosphonic acid
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additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
9-methyl-beta-carbolinium ion
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1 mM, stimulates
dithiothreitol
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required
phosphite
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.084 - 50
D-glyceraldehyde 3-phosphate
2.3
dihydroxyacetone 3-phosphate
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at pH 7.5 and 37C
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0.0025 - 18
dihydroxyacetone phosphate
0.26 - 2.5
glycerone phosphate
additional information
additional information
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.25 - 57500000
D-glyceraldehyde 3-phosphate
327
dihydroxyacetone 3-phosphate
Saccharomyces cerevisiae
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at pH 7.5 and 37C
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0.06 - 800
dihydroxyacetone phosphate
63 - 1080
glycerone phosphate
additional information
additional information
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
-1019000000 - 1269000000
D-glyceraldehyde 3-phosphate
750
dihydroxyacetone 3-phosphate
Saccharomyces cerevisiae
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at pH 7.5 and 37C
194880
2 - 580
dihydroxyacetone phosphate
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.05
2-(N-formyl-N-hydroxy)-aminoethyl phosphonate
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0.019 - 101
2-Phosphoglycolate
0.4
3-phospho-D-glycerate
pH 6.5, 70C
1.9 - 5
3-phosphoglycerate
3.8 - 31
arsenate
4.9 - 17.9
AsO43-
1.8
glycerol 1-phosphate
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0.661
phosphoenolpyruvate
pH 6.5, 70C
0.0034
phosphoglycoloaldoxime
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-
0.111
phosphoglycolohydrazide
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-
0.003
Phosphoglycolohydroxamate
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-
0.159
[3-amino-3-(hydroxyimino)propyl]phosphonic acid
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