Information on EC 4.1.2.13 - fructose-bisphosphate aldolase

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

EC NUMBER
COMMENTARY hide
4.1.2.13
-
RECOMMENDED NAME
GeneOntology No.
fructose-bisphosphate aldolase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
condensation
-
-
-
-
elimination
-
-
of an aldehyde, C-C bond cleavage
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
1,3-propanediol biosynthesis (engineered)
-
-
Biosynthesis of antibiotics
-
-
Biosynthesis of secondary metabolites
-
-
Calvin-Benson-Bassham cycle
-
-
Carbon fixation in photosynthetic organisms
-
-
formaldehyde assimilation II (RuMP Cycle)
-
-
formaldehyde assimilation III (dihydroxyacetone cycle)
-
-
Fructose and mannose metabolism
-
-
gluconeogenesis I
-
-
gluconeogenesis II (Methanobacterium thermoautotrophicum)
-
-
gluconeogenesis III
-
-
glycolysis
-
-
Glycolysis / Gluconeogenesis
-
-
glycolysis I (from glucose 6-phosphate)
-
-
glycolysis II (from fructose 6-phosphate)
-
-
glycolysis III (from glucose)
-
-
glycolysis IV (plant cytosol)
-
-
glycolysis V (Pyrococcus)
-
-
Metabolic pathways
-
-
Methane metabolism
-
-
Microbial metabolism in diverse environments
-
-
Pentose phosphate pathway
-
-
photosynthesis
-
-
sucrose biosynthesis I (from photosynthesis)
-
-
sucrose degradation V (sucrose alpha-glucosidase)
-
-
SYSTEMATIC NAME
IUBMB Comments
D-fructose-1,6-bisphosphate D-glyceraldehyde-3-phosphate-lyase (glycerone-phosphate-forming)
Also acts on (3S,4R)-ketose 1-phosphates. The yeast and bacterial enzymes are zinc proteins. The enzymes increase electron-attraction by the carbonyl group, some (Class I) forming a protonated imine with it, others (Class II), mainly of microbial origin, polarizing it with a metal ion, e.g. zinc.
CAS REGISTRY NUMBER
COMMENTARY hide
9024-52-6
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Anacystis sp.
-
-
-
Manually annotated by BRENDA team
strain G2
EMBL
Manually annotated by BRENDA team
strain G2
EMBL
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain NRRL 3435, strain NRRL 447, strain NRRL 480 and strain NRRL 3484
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
cv. Victory 1, oat
-
-
Manually annotated by BRENDA team
strain ATCC 19213
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
golden-mantled ground squirrel
-
-
Manually annotated by BRENDA team
Candida sp.
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Chlamydomonas sp.
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Crookes' strain
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Euglena sp.
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain 2S
-
-
Manually annotated by BRENDA team
strain 2S
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
C3KO or wild-type mice
-
-
Manually annotated by BRENDA team
CDC No. 46
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain 228
-
-
Manually annotated by BRENDA team
strain 228
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
i.e. Thermoproteus neutrophilus
UniProt
Manually annotated by BRENDA team
-
Uniprot
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Formosan strain
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
PCC 6803
-
-
Manually annotated by BRENDA team
exhibits light-activated heterotrophic growth (LAHG) under dark conditions with glucose as a carbon source
UniProt
Manually annotated by BRENDA team
strain GK24
Uniprot
Manually annotated by BRENDA team
strain GK24
Uniprot
Manually annotated by BRENDA team
Veillonella sp.
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
-
chloroplastic fructose 1,6-bisphosphate aldolase isoforms are methylated by protein-lysine methyltransferase LSMT. Trimethylation occurs at a conserved lysyl residue located close to the C terminus. Trimethylation does not modify the kinetic properties and tetrameric organization of the aldolases in vitro
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
2 acetaldehyde
5-deoxy-D-threo-2-pentulose
show the reaction diagram
2 butyraldehyde
5,6,7-trideoxy-D-threo-2-heptulose
show the reaction diagram
2 D-glyceraldehyde
D-fructose
show the reaction diagram
-
-
yield 60%
-
?
2 pentanaldehyde
5,6,7,8-tetradeoxy-D-threo-2-octulose
show the reaction diagram
2 propionaldehyde
5,6-dideoxy-D-threo-2-hexulose
show the reaction diagram
5-fluoro-5-deoxy-D-ribulose 1-phosphate
fluoroacetaldehyde + dihydroxyacetone phosphate
show the reaction diagram
-
-
-
-
r
D-fructose 1,6-bisphosphate
dihydroxyacetone phosphate + D-glyceraldehyde 3-phosphate
show the reaction diagram
D-fructose 1,6-bisphosphate
dihydroxyacetone phosphate + glyceraldehyde 3-phosphate
show the reaction diagram
-
aldolase is involved in the metabolism of fructose, converting fructose 1-phosphate to dihydroxyacetone phosphate and glyceraldehyde
-
-
r
D-fructose 1,6-bisphosphate
dihydroxyacetone phosphate + glyceraldehyde-3-phosphate
show the reaction diagram
-
-
-
-
?
D-fructose 1,6-bisphosphate
glycerone phosphate + D-glyceraldehyde 3-phosphate
show the reaction diagram
D-Fructose 1-phosphate
Glycerone phosphate + D-glyceraldehyde
show the reaction diagram
D-fructose-1,6-bisphosphate
dihydroxyacetone phosphate + glyceraldehyde-3-phosphate
show the reaction diagram
D-fructose-1,6-bisphosphate
glyceraldehyde-3-phosphate + dihydroxyacetone phosphate
show the reaction diagram
-
-
-
-
r
D-glyceraldehyde 3-phosphate + glycerone phosphate
tagatose-1,6-bisphosphate
show the reaction diagram
-
-
-
?
D-Xylulose 1-phosphate
?
show the reaction diagram
-
110% of the activity with fructose 1,6-diphosphate
-
-
-
dihydroxyacetone + phenyl [(2R)-1-oxopropan-2-yl]carbamate
phenyl [(2R,3R,4S)-3,4,6-trihydroxy-5-oxohexan-2-yl]carbamate
show the reaction diagram
-
i.e. (S)-N-Cbz-alaninal,substrate only for mutant A129S/A165G
aldol adduct is a key intermediates for the expedient synthesis of the pyrrolidine type iminocyclitol, 2,5-imino-1,2,5-trideoxy-D-mannitol
-
?
dihydroxyacetone + phenyl [(2S)-1-oxopropan-2-yl]carbamate
phenyl [(2S,3R,4S)-3,4,6-trihydroxy-5-oxohexan-2-yl]carbamate
show the reaction diagram
-
i.e. (S)-N-Cbz-alaninal, substrate only for mutant A129S/A165G
aldol adduct is a key intermediates for the expedient synthesis of the pyrrolidine type iminocyclitol, 2,5-imino-1,2,5-trideoxy-D-glucitol
-
?
dihydroxyacetone phosphate
?
show the reaction diagram
dihydroxyacetone phosphate + D-glyceraldehyde 3-phosphate
D-fructose 1,6-bisphosphate
show the reaction diagram
Glycerone phosphate + D-glyceraldehyde
Fructose 1-phosphate
show the reaction diagram
-
-
-
-
Glycerone phosphate + D-glyceraldehyde 3-phosphate
D-Fructose 1,6-bisphosphate
show the reaction diagram
hydroxyacetone + phenoxyacetaldehyde
?
show the reaction diagram
-
substrate only for mutant A129S/A165G
-
-
?
hydroxyacetone + phenyl (2-oxoethyl)carbamate
?
show the reaction diagram
-
substrate only for mutant A129S/A165G
-
-
?
hydroxyacetone + phenyl (3-oxopropyl)carbamate
?
show the reaction diagram
-
substrate only for mutant A129S/A165G
-
-
?
hydroxyacetone + phenyl [(2R)-1-oxopropan-2-yl]carbamate
phenyl [(2R,3R,4S)-3,4-dihydroxy-5-oxohexan-2-yl]carbamate
show the reaction diagram
-
substrate only for mutant A129S/A165G
-
-
?
hydroxyacetone + phenyl [(2S)-1-oxopropan-2-yl]carbamate
phenyl [(2S,3R,4S)-3,4-dihydroxy-5-oxohexan-2-yl]carbamate
show the reaction diagram
-
substrate only for mutant A129S/A165G
-
-
?
L-glyceraldehyde
L-sorbose
show the reaction diagram
-
-
yield 28%
-
?
propanal + dihydroxyacetone phosphate
?
show the reaction diagram
-
-
-
?
sedoheptulose 1,7-bis-phosphate
?
show the reaction diagram
-
-
-
-
?
sedoheptulose 1,7-bis-phosphate
glycerone phosphate + D-erythrose 4-phosphate
show the reaction diagram
sedoheptulose 1,7-bisphosphate
?
show the reaction diagram
-
-
-
?
sedoheptulose 1,7-bisphosphate
glycerone phosphate + D-erythrose 4-phosphate
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-fructose 1,6-bisphosphate
dihydroxyacetone phosphate + glyceraldehyde 3-phosphate
show the reaction diagram
-
aldolase is involved in the metabolism of fructose, converting fructose 1-phosphate to dihydroxyacetone phosphate and glyceraldehyde
-
-
r
D-fructose 1,6-bisphosphate
glycerone phosphate + D-glyceraldehyde 3-phosphate
show the reaction diagram
D-fructose-1,6-bisphosphate
dihydroxyacetone phosphate + glyceraldehyde-3-phosphate
show the reaction diagram
D-fructose-1,6-bisphosphate
glyceraldehyde-3-phosphate + dihydroxyacetone phosphate
show the reaction diagram
-
-
-
-
r
Glycerone phosphate + D-glyceraldehyde 3-phosphate
D-Fructose 1,6-bisphosphate
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe3+
-
maximal activity only when both 8 mM Cys and 0.1 mM Fe2+ are present. Fe3+ or Mn2+ can replace Fe2+
FeSO4
the enzyme requires divalent cation for activity. The highest activity is obtained with MnCl2 (100%, 50 U/mg), which can be partially replaced by FeSO4 (40% residual activity)
LiCl
-
the enzyme activity is enhanced by increasing KCl and NaCl concentrations. Optimum activity is diaplayed in 2.5 M KCl, while that in equimolar NaCl is lower. However, aldolase is less active in NH4CI and LiCI
MnCl2
the enzyme requires divalent cation for activity. The highest activity is obtained with MnCl2 (100%, 50 U/mg), which can be partially replaced by FeSO4 (40% residual activity)
NaCl
-
the enzyme activity is enhanced by increasing KCl and NaCl concentrations. Optimum activity is diaplayed in 2.5 M KCl, while that in equimolar NaCl is lower. However, aldolase is less active in NH4CI and LiCI
NH4Cl
-
the enzyme activity is enhanced by increasing KCl and NaCl concentrations. Optimum activity is diaplayed in 2.5 M KCl, while that in equimolar NaCl is lower. However, aldolase is less active in NH4CI and LiCI
Ni2+
-
addition of Cu2+, Fe2+, Ni2+, Mg2+, and Mn2+ leads to only a small level of recovery of activity
Rb+
-
enhances activity of aldolase II
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(NH4)2SO4
([3-hydroxy-2-oxo-4-[(phosphonomethoxy)methyl]pyridin-1(2H)-yl]methyl)phosphonic acid
-
-
([3-hydroxy-2-oxo-4-[2-(phosphonooxy)ethyl]pyridin-1(2H)-yl]methyl)phosphonic acid
-
-
([3-hydroxy-4-[(1R)-1-hydroxy-2-(phosphonooxy)ethyl]-2-oxopyridin-1(2H)-yl]methyl)phosphonic acid
-
-
([3-hydroxy-4-[(1S)-1-hydroxy-2-(phosphonooxy)ethyl]-2-oxopyridin-1(2H)-yl]methyl)phosphonic acid
-
-
([4,5-dihydroxy-6-[2-(phosphonooxy)ethyl]pyridin-3-yl]methyl)phosphonic acid
-
-
1,10-phenanthroline
1-hydroxy-2-naphthaldehyde 6-phosphate
-
slow-binding
2,2'-bipyridyl
-
2 mM, 76% inhibition
2,2'-dipyridyl
-
aldolase class II
2,4-Dihydroxybenzaldehyde 4-phosphate
-
-
2-(3-hydroxy-2-oxo-1,2-dihydropyridin-4-yl)ethyl dihydrogen phosphate
-
-
2-(3-hydroxy-2-oxo-1,2-dihydropyridin-4-yl)ethyl phosphate
2-carboxy-6-(phosphonomethyl)pyridinium chloride
2-hydroxy-2-(3-hydroxy-2-oxo-1,2-dihydropyridin-4-yl)ethyl dihydrogen phosphate
-
-
2-mercaptoethanol
2-oxo-2-[(phenylsulfonyl)amino]ethyl phosphate
-
-
2-oxoglutarate
-
-
2-propanol
-
at 12.5% (v/v) remaining activity, 69.99%, and 25% (v/v) remaining activity, 3.72%
2-[(methylsulfonyl)amino]-2-oxoethyl phosphate
-
-
2-[(trihydroxyphosphoranyl)oxy]acetohydrazide
2-[hydroxy(3-hydroxypropyl)amino]-2-oxoethyl dihydrogen phosphate
2-[hydroxy(4-hydroxybutyl)amino]-2-oxoethyl dihydrogen phosphate
3-phosphoglycerate
-
-
3-[hydroxy[(phosphonooxy)acetyl]amino]propyl dihydrogen phosphate
4-Hydroxybenzaldehyde phosphate
-
competitive
-
4-[hydroxy[(phosphonooxy)acetyl]amino]butyl hexanoate
5,5’-dithiobis(2-nitrobenzoic acid)
-
1 mM, complete inhibition
-
5-chloro-8-hydroxyquinoline
-
non-competitive (mixed type)
5-formyl-6-hydroxynaphthalen-2-yl dihydrogen phosphate
6-phosphogluconate
-
-
8-hydroxyquinoline
Agaricic acid
-
50% inhibition at 0.03 mM
alpha-glycerophosphate
-
-
ascorbic acid
-
-
Benzene
-
at 12.5% (v/v) remaining activity, 88.94%, and 25% (v/v) remaining activity, 88.94%
Borohydride
Bromoacetate
-
-
butanol
-
-
Cd2+
1 mM, no residual activity; 1 mM, no residual activity
Chelators
-
-
-
citrate
Cr3+
1 mM, 36% decrease of activity
CuCl2
-
1 mM, complete inhibition
D-erythrose 4-phosphate
-
competitive
D-Erythrulose 1-phosphate
-
slow reversible
D-fructose 1,6-bisphosphate
substrate inhibition; substrate inhibition
D-glucitol 1,6-bisphosphate
D-hexitol-1,6-bisphosphate
-
-
D-mannitol 1,6-bisphosphate
D-mannitol-1,6-bisphosphate
-
competitive inhibitor
D-ribulose 1,5-bisphosphate
-
-
D-tagatose 1,6-bisphosphate
competitive inhibitor
dihydroxyacetone phosphate
dimethylsulfoxid
-
at 12.5% (v/v) remaining activity, 131.26%, and 25% (v/v) remaining activity, 133.2%
diphosphate
dipicolinic acid
erythrose 4-phosphate
-
-
ethanol
-
at 12.5% (v/v) remaining activity, 79.19%, and 25% (v/v) remaining activity, 33.41%
ethyl acetate
-
at 12.5% (v/v) remaining activity, 71.96%, and 25% (v/v) remaining activity, 41.62%
Fluorescein 5'-isothiocyanate
results in a minimal loss of enzyme activity
fructose 6-phosphate
-
-
glucose 1-phosphate
glucose 6-phosphate
-
-
glutathione
-
10 mM, 62% residual activity
glyceraldehyde 3-phosphate
glycerol
-
at 20% (v/v) reduced enzyme activity by 65%
Glycerol 2,3-diphosphate
-
-
glycerone phosphate
glyoxylate
-
-
hexane
-
at 12.5% (v/v) remaining activity, 98.25%, and 25% (v/v) remaining activity, 92.22%
hexitol-1,6-bisphosphate
-
strong competitive inhibitor
HgCl2
-
1 mM, complete inhibition
hydrogen peroxide
-
inhibitory at 0.25%, at pH 7
Hydroquinone diphosphate
-
competitive
iodoacetamide
-
76% residual activity at 10 mM
iodoacetate
L-cysteine
-
10 mM, complete inhibition
Magnesium citrate
mannitol-1,6-bis(phosphate)
-
competitive
N'-hydroxy-2-[(trihydroxyphosphoranyl)oxy]ethanimidamide
-
-
N,N-dimethylmethanamide
-
at 12.5% (v/v) remaining activity, 118.40%, and 25% (v/v) remaining activity, 73.93%
N-(3-hydroxypropyl)-glycolohydrazide-bisphosphate
N-(3-hydroxypropyl)-glycolohydroxamic acid bisphosphate
N-(3-hydroxypropyl)-phosphoglycolohydroxamic acid
N-(4-hydroxybutyl)-glycolohydroxamic acid bisphosphate
-
inhibitor attachment has no effect on the plasminogen binding activity of the enzyme but competes with the natural substrate, fructose 1,6-bisphosphate, and substantiates a reaction mechanism associated with metallodependent aldolases involving recruitment of the catalytic zinc ion by the substrate upon active site binding
-
N-hydroxy-2-[(trihydroxyphosphoranyl)oxy]acetamide
-
-
naphthalene-2,6-bisphosphate
-
strong competitive inhibitor
naphthyl 2,6-bisphosphate
-
competitive
Ni2+
-
cells stressed by 8 microM Ni(II) for 20 min lose 75% of their FbaA activity. In presence of 8 microM Ni(II), purified FbaA loses 80% of its activity within 2 min. Inhibition is due to Ni(II) binding to a secondary zinc binding site
o-phenanthroline
-
0.06 mM, inactivation
oxaloacetate
-
-
peroxynitrite
-
decrease of Vmax and KM for fructose-1,6-bisphosphate after incubation with peroxynitrite. Tyrosine residues in the carboxyl-terminal region of the aldolase are major targets of nitration. Tyrosine nitration of aldolase A can contribute to an impaired cellular glycolytic activity
phosphate
phosphatidylserine
-
-
phosphoenolpyruvate
phosphoglycolo hydroxamic acid
phosphoglycolo-amidoxime
-
PGA, i.e. 2-amino-2-(hydroxyimino)ethyl phosphate
phosphoglycolo-hydrazide
-
PGHz, i.e. 2-hydrazino-2-oxoethyl phosphate
phosphoglycoloamidoxime
phosphoglycolohydrazide
Phosphoglycolohydroxamate
Polyphosphate
-
-
Propanol
-
-
pyridoxal 5'-phosphate
pyruvate
-
-
Resorcinol diphosphate
-
competitive
ribose 5-phosphate
sulfhydryl reagents
-
-
suramin
tagatose 1,6-bisphosphate
-
-
Toluene
-
at 12.5% (v/v) remaining activity, 89.70%, and 25% (v/v) remaining activity, 91.02%
[(3-hydroxy-2-oxopyridin-1(2H)-yl)methyl]phosphonic acid
-
-
[2-(3-hydroxy-2-oxo-1,2-dihydropyridin-4-yl)ethyl]phosphonic acid
-
-
[[(3-hydroxy-2-oxo-1,2-dihydropyridin-4-yl)methoxy]methyl]phosphonic acid
-
-
[[3-hydroxy-2-oxo-4-(2-phosphonoethyl)pyridin-1(2H)-yl]methyl]phosphonic acid
-
-
additional information