Information on EC 3.5.1.66 - 2-(hydroxymethyl)-3-(acetamidomethylene)succinate hydrolase

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The expected taxonomic range for this enzyme is: Bacteria

EC NUMBER
COMMENTARY
3.5.1.66
-
RECOMMENDED NAME
GeneOntology No.
2-(hydroxymethyl)-3-(acetamidomethylene)succinate hydrolase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
2-(hydroxymethyl)-3-(acetamidomethylene)succinate + 2 H2O = acetate + 2-(hydroxymethyl)-4-oxobutanoate + NH3 + CO2
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
hydrolysis of linear amides
-
-
deaminating, decarboxylating
-
PATHWAY
KEGG Link
MetaCyc Link
Vitamin B6 metabolism
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SYSTEMATIC NAME
IUBMB Comments
2-(hydroxymethyl)-3-(acetamidomethylene)succinate amidohydrolase (deaminating, decarboxylating)
Involved in the degradation of pyridoxin by Pseudomonas and Arthrobacter.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
alpha-hydroxymethyl-alpha'-(N-acetylaminomethylene)succinic acid hydrolase
-
-
-
-
compound B hydrolase
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
95829-26-8
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
Arthrobacter sp. Cr-7
Cr-7
-
-
Manually annotated by BRENDA team
Pseudomonas sp. IA
IA
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-(hydroxymethyl)-3-(acetamidomethylene)succinate + H2O
acetate + 2-(hydroxymethyl)-4-oxobutanoate + NH3 + CO2
show the reaction diagram
Pseudomonas sp., Arthrobacter sp., Pseudomonas sp. IA, Pseudomonas sp. MA-1, Arthrobacter sp. Cr-7
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compound B, alpha-hydroxymethyl-alpha'-(N-acetylaminomethylene)succinic acid
-
?
2-(hydroxymethyl)-3-(acetamidomethylene)succinate + H2O
?
show the reaction diagram
-
compound B, alpha-hydroxymethyl-alpha'-(N-acetylaminomethylene)succinic acid
-
-
-
2-(hydroxymethyl)-3-(acetamidomethylene)succinate + H2O
?
show the reaction diagram
-
involved in pyridoxine degradation
-
-
-
2-(hydroxymethyl)-3-(acetamidomethylene)succinate + H2O
?
show the reaction diagram
Pseudomonas sp. IA, Pseudomonas sp. MA-1
-
compound B, alpha-hydroxymethyl-alpha'-(N-acetylaminomethylene)succinic acid
-
-
-
3-(acetamidomethylene)succinate + H2O
acetate + 4-oxobutanoate + NH3 + CO2
show the reaction diagram
Arthrobacter sp., Arthrobacter sp. Cr-7
-
compound A, alpha-(N-acetylaminomethylene)succinic acid: poor substrate
-
?
additional information
?
-
-
high substrate specificity, enzyme highly specific, inducible amidohydrolase
-
-
-
additional information
?
-
-
enzyme of vitamin B6 degradation, utilizing pyridoxine as sole source of carbon and nitrogen
-
-
-
additional information
?
-
Arthrobacter sp. Cr-7
-
high substrate specificity, enzyme highly specific, inducible amidohydrolase, enzyme of vitamin B6 degradation, utilizing pyridoxine as sole source of carbon and nitrogen
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
2-(hydroxymethyl)-3-(acetamidomethylene)succinate + H2O
?
show the reaction diagram
-
compound B, alpha-hydroxymethyl-alpha'-(N-acetylaminomethylene)succinic acid
-
-
-
2-(hydroxymethyl)-3-(acetamidomethylene)succinate + H2O
?
show the reaction diagram
-
involved in pyridoxine degradation
-
-
-
2-(hydroxymethyl)-3-(acetamidomethylene)succinate + H2O
?
show the reaction diagram
Pseudomonas sp. IA, Pseudomonas sp. MA-1
-
compound B, alpha-hydroxymethyl-alpha'-(N-acetylaminomethylene)succinic acid
-
-
-
additional information
?
-
Pseudomonas sp., Arthrobacter sp., Pseudomonas sp. IA, Pseudomonas sp. MA-1, Arthrobacter sp. Cr-7
-
enzyme of vitamin B6 degradation, utilizing pyridoxine as sole source of carbon and nitrogen
-
-
-
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
some inorganic cations activate
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
Dicarboxylic acids
-
competitive
diphosphate
-
competitive
Hg2+
-
0.01 mM, 15 min, 82% activity remains
Itaconic acid
-
competitive, most effective inhibitor, Ki: 0.74 mM
phosphate
-
competitive
sulfite
-
noncompetitive, inhibition by a time-dependent mechanism, addition of succinic semialdehyde protects against sulfite inhibition
Tricarboxylic acids
-
competitive
-
Zn2+
-
1 mM: 40% inhibition
malonate
-
competitive, Ki: 20 mM
additional information
-
no inhibition by: organic protein reagents, 0.1 mM, 15 min, p-chloromercuribenzoate, 1.0 mM Ni2+, 1.0 mM Co2+, 1.0 mM Mn2+, 1.0 mM Mg2+, 1.0 mM Ca2+, 1.0 mM Cu2+, 1.0 mM Cs+, 1.0 mM Li+, SO42-, NO3-, Cl-, 10 mM dithiothreitol, 100 mM monocarboxylic acids
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.025
-
2-(Hydroxymethyl)-3-(acetamidomethylene)succinate
-
compound B, 25C, Tris-HCl, pH 7.0
0.123
-
2-(Hydroxymethyl)-3-(acetamidomethylene)succinate
-
compound B, 2-(N-morpholino)ethane-sulfonic acid, pH 6.0
0.25
-
2-(Hydroxymethyl)-3-(acetamidomethylene)succinate
-
compound B, Tris-HCl, pH 8.0
0.56
-
2-(Hydroxymethyl)-3-(acetamidomethylene)succinate
-
compound B, 2-(N-morpholino)ethane-sulfonic acid, pH 6.5
0.68
-
3-(acetamidomethylene)succinate
-
compound A, 25C, pH 7.0
-
additional information
-
additional information
-
kinetic data
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TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
2.3
-
2-(Hydroxymethyl)-3-(acetamidomethylene)succinate
-
turnover no./subunit, 25C
Ki VALUE [mM]
Ki VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.74
-
Itaconic acid
-
competitive, most effective inhibitor
20
-
malonate
-
competitive
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
3.79
-
-
25C
additional information
-
-
-
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
-
pI: 4.2, effect of buffer on pH optimum
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
25
-
-
assay at
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
205000
-
-
Cr-7, gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
multimer
-
Cr-7, probably six identical subunits, 6 * 36600, SDS-PAGE
multimer
Arthrobacter sp. Cr-7
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Cr-7, probably six identical subunits, 6 * 36600, SDS-PAGE
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pH STABILITY
pH STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
4
5
-
rapid loss of activity
6
10
-
stable at room temperature
8
-
-
70C, 1 min, stable at
TEMPERATURE STABILITY
TEMPERATURE STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
70
-
-
pH 8.0, 1 min, stable at
100
-
-
1 min, 65% activity retained
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
Cr-7, -20C, 0.1 M Tris-HCl, pH 7.0, stable for several months
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Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE