Information on EC 4.1.2.11 - hydroxymandelonitrile lyase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
4.1.2.11
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RECOMMENDED NAME
GeneOntology No.
hydroxymandelonitrile lyase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(S)-4-Hydroxymandelonitrile = cyanide + 4-hydroxybenzaldehyde
show the reaction diagram
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
cyanohydrin formation
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-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
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Cyanoamino acid metabolism
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dhurrin degradation
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SYSTEMATIC NAME
IUBMB Comments
(S)-4-hydroxymandelonitrile 4-hydroxybenzaldehyde-lyase (cyanide-forming)
Does not accept aliphatic hydroxynitriles, unlike EC 4.1.2.10 (mandelonitrile lyase), EC 4.1.2.46 [aliphatic (R)-hydroxynitrile lyase] and EC 4.1.2.47 [(S)-hydroxynitrile ketone-lyase (cyanide forming)].
CAS REGISTRY NUMBER
COMMENTARY hide
9075-38-1
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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-
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(S)-4-Hydroxymandelonitrile
Cyanide + 4-hydroxybenzaldehyde
show the reaction diagram
(S)-Mandelonitrile
?
show the reaction diagram
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-
-
-
-
(S)-Mandelonitrile
Cyanide + benzaldehyde
show the reaction diagram
4-Hydroxymandelonitrile
?
show the reaction diagram
Benzaldehyde + cyanide
(S)-Mandelonitrile
show the reaction diagram
-
-
-
-
?
cyanide + 4-hydroxybenzaldehyde
(S)-4-hydroxymandelonitrile
show the reaction diagram
cyanide + 4-hydroxybenzaldehyde
(S)-p-hydroxymandelonitrile
show the reaction diagram
-
-
-
?
HCN + 3-phenylpropionaldehyde
(2S)-2-hydroxy-4-phenylbutanenitrile
show the reaction diagram
-
-
17% enantiomeric excess
?
HCN + 3-phenylpropionaldehyde
2-hydroxy-4-phenylbutanenitrile
show the reaction diagram
-
-
-
?
HCN + 4-hydroxybenzaldehyde
(S)-4-hydroxymandelonitrile
show the reaction diagram
HCN + 4-hydroxybenzaldehyde
(S)-p-hydroxymandelonitrile
show the reaction diagram
-
-
-
?
HCN + acrolein
(2S)-2-hydroxybut-3-enenitrile
show the reaction diagram
-
-
25% enantiomeric excess
?
HCN + acrolein
2-hydroxybut-3-enenitrile
show the reaction diagram
-
-
-
?
HCN + benzaldehyde
(S)-mandelonitrile
show the reaction diagram
isovanillin cyanohydrin
cyanide + isovanillin
show the reaction diagram
vanillin cyanohydrin
cyanide + vanillin
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
(S)-4-Hydroxymandelonitrile
Cyanide + 4-hydroxybenzaldehyde
show the reaction diagram
P52708
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-
?
(S)-Mandelonitrile
?
show the reaction diagram
-
-
-
-
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4-Hydroxymandelonitrile
?
show the reaction diagram
cyanide + 4-hydroxybenzaldehyde
(S)-4-hydroxymandelonitrile
show the reaction diagram
-
-
-
r
cyanide + 4-hydroxybenzaldehyde
(S)-p-hydroxymandelonitrile
show the reaction diagram
-
-
-
?
HCN + 4-hydroxybenzaldehyde
(S)-p-hydroxymandelonitrile
show the reaction diagram
-
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
no requirement for metal ions
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
CuSO4
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Fe2(SO4)3
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HgCl2
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p-Chloromercuriphenylsulfonic acid
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additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.28 - 11
(R,S)-mandelonitrile
4.1
(S)-4-hydroxymandelonitrile
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pH 5.0, 25C
5.9
4-hydroxybenzaldehyde
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pH 5.0, 25C
0.55
4-hydroxymandelonitrile
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179
cyanide
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pH 5.0, 25C
0.7
D,L-hydroxymandelonitrile
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1.2
D,L-isovanillin cyanohydrin
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0.79
D,L-mandelonitrile
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0.73
D,L-vanillin cyanohydrin
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
188
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4-hydroxymandelonitrile
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3.2 - 6.3
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3.5 - 6.5
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4
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40% of maxinmum activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
-5 - 25
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when the temperature decreases from 25C to -5C, the enantiomeric excess increases from 18% to 30%
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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soluble cytoplasm, microsomal or vacuolar location
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
23000
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2 * 23000 + 2 * 33000, SDS-PAGE, reducing conditions
29000
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4 * 29000, lyase 1, SDS-PAGE
36500
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1 * 36500, lyase 2, SDS-PAGE
38000
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lyase 2, gel filtration
95000 - 105000
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gel filtration
105000
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108000
180000
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sedimentation equilibrium centrifugation
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 33000 + x * 22000
heterotetramer
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alpha2,beta2 heterotetramer consisting of two alpha,beta heterodimers
monomer
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1 * 36500, lyase 2, SDS-PAGE
tetramer
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
enzyme in complex with the inhibitor benzoic acid determined at 2.3 A resolution and refined to a crystallographic R-factor of 16.5%, space group C2, cell dimensions a = 150.7 A, b = 103.7 A, c = 90.6 A, beta = 101.3
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2 - 10
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37321
4 - 6
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4890
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0 - 20
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stable
35
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thermal inactivation above
37
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half-life 64 h
70
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30 min, complete inactivation
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-15C, no loss of activity after 3 months
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
lyase 1 and lyase 2
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis