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Information on EC 4.1.2.11 - hydroxymandelonitrile lyase and Organism(s) Sorghum bicolor and UniProt Accession P52708
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4.1.2.11 hydroxymandelonitrile lyaseIUBMB Comments
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)].
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Word Map
The taxonomic range for the selected organisms is: Sorghum bicolor
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Synonyms
hydroxynitrile lyase, oxynitrilase, sbhnl, (s)-hnl, s-oxynitrilase, (s)-p-hydroxy-mandelonitrile lyase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(S)-HNL
(S)-Hydroxynitrile lyase
-
-
-
-
(S)-p-Hydroxy-mandelonitrile lyase
-
-
-
-
HNL
Hydroxynitrile lyase
Lyase, hydroxymandelonitrile
-
-
-
-
Oxynitrilase
-
-
-
-
S-Oxynitrilase
-
-
-
-
SbHNL
-
-
-
-
(S)-HNL
-
-
-
-
HNL
-
-
-
-
Hydroxynitrile lyase
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
cyanohydrin formation
-
-
-
-
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
9075-38-1
-
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
(S)-4-Hydroxymandelonitrile
Cyanide + 4-hydroxybenzaldehyde
-
-
?
cyanide + 4-hydroxybenzaldehyde
(S)-p-hydroxymandelonitrile
-
-
?
HCN + 3-phenylpropionaldehyde
(2S)-2-hydroxy-4-phenylbutanenitrile
-
-
17% enantiomeric excess
?
HCN + acrolein
(2S)-2-hydroxybut-3-enenitrile
-
-
25% enantiomeric excess
?
HCN + 4-hydroxybenzaldehyde
(S)-4-hydroxymandelonitrile
(S)-specific
-
?
HCN + 4-hydroxybenzaldehyde
(S)-4-hydroxymandelonitrile
(S)-specific
-
?
(S)-4-Hydroxymandelonitrile
Cyanide + 4-hydroxybenzaldehyde
-
inactive against 2-hydroxymanelonitrile or 3-hydroxymandelonitrile
-
?
4-Hydroxymandelonitrile
?
-
involved in cyanogenesis through its ability to catalyze the stereospecific retro-addition of cyanohydrins into toxic HCN and a carbonyl compound
-
-
?
HCN + 4-hydroxybenzaldehyde
(S)-4-hydroxymandelonitrile
-
(S)-specific
-
?
vanillin cyanohydrin
cyanide + vanillin
-
20% the rate of 4-hydroxybenzaldehyde
-
?
additional information
?
-
substrate range of SbHNL is limited to aromatic and heteroaromatic aldehydes, does not accept aliphatic aldehydes as substrates
-
-
?
additional information
?
-
-
substrate range of SbHNL is limited to aromatic and heteroaromatic aldehydes, does not accept aliphatic aldehydes as substrates
-
-
?
additional information
?
-
substrate range of SbHNL is limited to aromatic and heteroaromatic aldehydes, does not accept aliphatic aldehydes as substrates
-
?
additional information
?
-
-
substrate range of SbHNL is limited to aromatic and heteroaromatic aldehydes, does not accept aliphatic aldehydes as substrates
-
?
additional information
?
-
substrate range of SbHNL is limited to aromatic and heteroaromatic aldehydes, does not accept aliphatic aldehydes as substrates
-
-
?
additional information
?
-
substrate range of SbHNL is limited to aromatic and heteroaromatic aldehydes, does not accept aliphatic aldehydes as substrates
-
?
additional information
?
-
-
substrate range of SbHNL is limited to aromatic and heteroaromatic aldehydes, does not accept aliphatic aldehydes as substrates
-
-
?
additional information
?
-
-
substrate range of SbHNL is limited to aromatic and heteroaromatic aldehydes, does not accept aliphatic aldehydes as substrates
-
?
additional information
?
-
-
When the temperature decreases from 25°C to -5°C, the enantiomeric excess increases from 18% to 30%
-
-
?
additional information
?
-
-
When the temperature decreases from 25°C to -5°C, the enantiomeric excess increases from 18% to 30%
-
?
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
(S)-4-Hydroxymandelonitrile
Cyanide + 4-hydroxybenzaldehyde
-
-
?
cyanide + 4-hydroxybenzaldehyde
(S)-p-hydroxymandelonitrile
-
-
?
4-Hydroxymandelonitrile
?
-
involved in cyanogenesis through its ability to catalyze the stereospecific retro-addition of cyanohydrins into toxic HCN and a carbonyl compound
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
not inhibited by iodoacetamide, p-chloromercuribenzoate, 2,2'-dipyridyl, 1,10-phenanthroline, phenylthiourea, NaCN, FeSO4, Na2S
-
additional information
-
not inhibited by iodoacetamide, p-chloromercuribenzoate, 2,2'-dipyridyl, 1,10-phenanthroline, phenylthiourea, NaCN, FeSO4, Na2S
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
-5 - 25
-
when the temperature decreases from 25°C to -5°C, the enantiomeric excess increases from 18% to 30%
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
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). HNLS_SORBI
510
1
56319
Swiss-Prot
Chloroplast (Reliability: 5)
PDB
SCOP
CATH
UNIPROT
ORGANISM
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
22000
33000
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
heterotetramer
alpha2,beta2 heterotetramer consisting of two alpha,beta heterodimers
tetramer
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
glycoprotein
-
both types of subunits are glycosylated, types of sugar: alpha-D-mannose, alpha-D-glucose, alpha D-galactose, alpha-D-N-acetylglucosmaine
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°
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
50
-
60% loss of activity after 5 min, protein impurities in crude extract protect
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
first (S)-HNL used in organic solvents for the preparation of (S)-cyanohydrins
synthesis
-
biocatalyst for the enantiospecific addition of hydrogen cyanide to aldehydes in organic solvents
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Bove, C.; Conn, E.E.
Metabolism of aromatic compounds in higher plants. II. Purification and properties of the oxynitrilase of Sorghum vulgare
J. Biol. Chem.
236
207-210
1961
Sorghum bicolor
-
Seely, M.K.; Criddle, R.S.; Conn, E.E.
The metabolism of aromatic compounds in higher plants. VII. On the requirement of hydroxynitrile lyase for plants
J. Biol. Chem.
241
4457-4462
1966
Sorghum bicolor
Seely, M.K.; Conn, E.E.
Hydroxynitrile lyase (Sorghum vulgare)
Methods Enzymol.
17B
239-244
1971
Sorghum bicolor
-
Kojima, M.; Poulton, J.E.; Thayer, S.S.; Conn, E.E.
Tissue distributions of dhurrin and of enzymes involved in its metabolism in leaves of Sorghum bicolor
Plant Physiol.
63
1022-1028
1979
Sorghum bicolor
Thayer, S.S.; Conn, E.E.
Subcellular localization of dhurrin beta-glucosidase and hydroxynitrile lyase in the mesophyll cells of Sorghum leaf blades
Plant Physiol.
67
617-622
1981
Sorghum bicolor
Wajant, H.; Mundry, K.W.
Hydroxynitrile lyase from Sorghum bicolor: a glycoprotein heterotetramer
Plant Sci.
89
127-133
1993
Sorghum bicolor
-
Wajant, H.; Boettinger, H.; Mundry, K.W.
Purification of hydroxynitrile lyase from Sorghum bicolor L. (sorghum) by affinity chromatography using monoclonal antibodies
Biotechnol. Appl. Biochem.
18
75-82
1993
Sorghum bicolor
-
Lauble, H.; Knoedler, S.; Schindelin, H.; Foerster, S.; Wajant, H.; Effenberger, F.
Crystallographic studies and preliminary X-ray investigation of (S)-p-hydroxy-mandelonitrile lyase from Sorghum bicolor L.
Acta Crystallogr. Sect. D
52
887-889
1996
Sorghum bicolor
Woker, R.; Champluvier, B.; Kula, M.R.
Purification of S-oxynitrilase from Sorghum bicolor by immobilized metal ion chromatography on different carrier metals
J. Chromatogr.
584
85-92
1992
Sorghum bicolor
Jansen, I.; Woker, R.; Kula, M.R.
Purification and protein characterization of hydroxynitrile lyases from sorghum and almond
Biotechnol. Appl. Biochem.
15
90-99
1992
Sorghum bicolor
-
Lauble, H.; Miehlich, B.; Foerster, S.; Wajant, H.; Effenberger, F.
Crystal structure of hydroxynitrile lyase from Sorghum bicolor in complex with the inhibitor benzoic acid: a novel cyanogenic enzyme
Biochemistry
41
12043-12050
2002
Sorghum bicolor (P52708), Sorghum bicolor
Effenberger, F.; Foerster, S.; Wajant, H.
Hydroxynitrile lyases in stereoselective catalysis
Curr. Opin. Biotechnol.
11
532-539
2000
Sorghum bicolor
Costes, D.; Wehtje, E.; Adlercreutz, P.
Hydroxynitrile lyase-catalyzed synthesis of cyanohydrins in organic solvents. Parameters influencing activity and enantiospecificity
Enzyme Microb. Technol.
25
384-391
1999
Sorghum bicolor
-
Gruber, K.; Kratky, C.
Biopolymers for biocatalysis: Structure and catalytic mechanism of hydroxynitrile lyases
J. Polym. Sci. A
42
479-486
2004
Sorghum bicolor (P52708)
-
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