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Information on EC 4.1.2.11 - hydroxymandelonitrile lyase
for references in articles please use BRENDA:EC4.1.2.11
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EC Tree 4 Lyases
4.1 Carbon-carbon lyases
4.1.2 Aldehyde-lyases
4.1.2.11 hydroxymandelonitrile lyase
IUBMB 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)].
The enzyme appears in viruses and cellular organisms
showSynonyms
hydroxynitrile lyase, oxynitrilase, sbhnl, (s)-hnl, s-oxynitrilase, (s)-p-hydroxy-mandelonitrile lyase, more
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SYNONYM 
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
-
-
-
-
(S)-Hydroxynitrile lyase
-
-
-
-
HNL
-
-
-
-
Hydroxynitrile lyase
-
-
-
-
SbHNL
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(S)-4-Hydroxymandelonitrile = cyanide + 4-hydroxybenzaldehyde
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
cyanohydrin formation
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
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)].
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CAS REGISTRY NUMBER
COMMENTARY
9075-38-1
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
Benzaldehyde + cyanide
(S)-Mandelonitrile
-
Substrates: -
Products: -
Products: -
?
cyanide + 4-hydroxybenzaldehyde
(S)-p-hydroxymandelonitrile
Substrates: -
Products: -
Products: -
?
HCN + 3-phenylpropionaldehyde
(2S)-2-hydroxy-4-phenylbutanenitrile
-
Substrates: -
Products: 17% enantiomeric excess
Products: 17% enantiomeric excess
?
HCN + 3-phenylpropionaldehyde
2-hydroxy-4-phenylbutanenitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 4-hydroxybenzaldehyde
(S)-p-hydroxymandelonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + acrolein
(2S)-2-hydroxybut-3-enenitrile
-
Substrates: -
Products: 25% enantiomeric excess
Products: 25% enantiomeric excess
?
isovanillin cyanohydrin
cyanide + isovanillin
-
Substrates: -
Products: -
Products: -
?
(S)-4-Hydroxymandelonitrile
Cyanide + 4-hydroxybenzaldehyde
-
Substrates: -
Products: -
Products: -
r
(S)-4-Hydroxymandelonitrile
Cyanide + 4-hydroxybenzaldehyde
-
Substrates: -
Products: -
Products: -
?
(S)-4-Hydroxymandelonitrile
Cyanide + 4-hydroxybenzaldehyde
Substrates: -
Products: -
Products: -
?
(S)-4-Hydroxymandelonitrile
Cyanide + 4-hydroxybenzaldehyde
-
Substrates: inactive against 2-hydroxymanelonitrile or 3-hydroxymandelonitrile
Products: -
Products: -
?
(S)-4-Hydroxymandelonitrile
Cyanide + 4-hydroxybenzaldehyde
-
Substrates: -
Products: -
Products: -
?
4-Hydroxymandelonitrile
?
-
Substrates: involved in cyanogenesis through its ability to catalyze the stereospecific retro-addition of cyanohydrins into toxic HCN and a carbonyl compound
Products: -
Products: -
?
4-Hydroxymandelonitrile
?
-
Substrates: cyanogenesis of higher plants
Products: -
Products: -
?
cyanide + 4-hydroxybenzaldehyde
(S)-4-hydroxymandelonitrile
-
Substrates: -
Products: -
Products: -
r
cyanide + 4-hydroxybenzaldehyde
(S)-4-hydroxymandelonitrile
-
Substrates: -
Products: -
Products: -
r
HCN + 4-hydroxybenzaldehyde
(S)-4-hydroxymandelonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 4-hydroxybenzaldehyde
(S)-4-hydroxymandelonitrile
-
Substrates: (S)-specific
Products: -
Products: -
?
HCN + 4-hydroxybenzaldehyde
(S)-4-hydroxymandelonitrile
Substrates: (S)-specific
Products: -
Products: -
?
HCN + benzaldehyde
(S)-mandelonitrile
-
Substrates: -
Products: 99% enantiomeric excess
Products: 99% enantiomeric excess
?
vanillin cyanohydrin
cyanide + vanillin
-
Substrates: 20% the rate of 4-hydroxybenzaldehyde
Products: -
Products: -
?
additional information
?
-
-
Substrates: substrate range of SbHNL is limited to aromatic and heteroaromatic aldehydes, does not accept aliphatic aldehydes as substrates
Products: -
Products: -
?
additional information
?
-
Substrates: substrate range of SbHNL is limited to aromatic and heteroaromatic aldehydes, does not accept aliphatic aldehydes as substrates
Products: -
Products: -
?
additional information
?
-
-
Substrates: substrate range of SbHNL is limited to aromatic and heteroaromatic aldehydes, does not accept aliphatic aldehydes as substrates
Products: -
Products: -
?
additional information
?
-
Substrates: substrate range of SbHNL is limited to aromatic and heteroaromatic aldehydes, does not accept aliphatic aldehydes as substrates
Products: -
Products: -
?
additional information
?
-
-
Substrates: When the temperature decreases from 25°C to -5°C, the enantiomeric excess increases from 18% to 30%
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(S)-4-Hydroxymandelonitrile
Cyanide + 4-hydroxybenzaldehyde
Substrates: -
Products: -
Products: -
?
cyanide + 4-hydroxybenzaldehyde
(S)-4-hydroxymandelonitrile
-
Substrates: -
Products: -
Products: -
r
cyanide + 4-hydroxybenzaldehyde
(S)-p-hydroxymandelonitrile
Substrates: -
Products: -
Products: -
?
HCN + 4-hydroxybenzaldehyde
(S)-p-hydroxymandelonitrile
-
Substrates: -
Products: -
Products: -
?
4-Hydroxymandelonitrile
?
-
Substrates: involved in cyanogenesis through its ability to catalyze the stereospecific retro-addition of cyanohydrins into toxic HCN and a carbonyl compound
Products: -
Products: -
?
4-Hydroxymandelonitrile
?
-
Substrates: cyanogenesis of higher plants
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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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
-
additional information
-
not inhibited by EDTA, 1,10-phenanthroline, 2,2'-dipyridyl
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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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%
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
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)
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
108000
22000
33000
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
heterotetramer
alpha2,beta2 heterotetramer consisting of two alpha,beta heterodimers
tetramer
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POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
glycoprotein
glycoprotein
-
both types of subunits are glycosylated, types of sugar: alpha-D-mannose, alpha-D-glucose, alpha D-galactose, alpha-D-N-acetylglucosmaine
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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
LITERATURE
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
50
60
50
-
60% loss of activity after 5 min, protein impurities in crude extract protect
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
-
biocatalyst for the enantiospecific addition of hydrogen cyanide to aldehydes in organic solvents
synthesis
first (S)-HNL used in organic solvents for the preparation of (S)-cyanohydrins
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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
-
brenda
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
brenda
Seely, M.K.; Conn, E.E.
Hydroxynitrile lyase (Sorghum vulgare)
Methods Enzymol.
17B
239-244
1971
Sorghum bicolor
-
brenda
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
brenda
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
brenda
Wajant, H.; Mundry, K.W.
Hydroxynitrile lyase from Sorghum bicolor: a glycoprotein heterotetramer
Plant Sci.
89
127-133
1993
Sorghum bicolor
-
brenda
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
-
brenda
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
brenda
Kuroki, G.W.; Conn, E.E.
Mandelonitrile lyase from Ximenia americana L.: stereospecificity and lack of flavin prosthetic group
Proc. Natl. Acad. Sci. USA
86
6978-6981
1989
Ximenia americana
brenda
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
brenda
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
-
brenda
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
brenda
Effenberger, F.; Foerster, S.; Wajant, H.
Hydroxynitrile lyases in stereoselective catalysis
Curr. Opin. Biotechnol.
11
532-539
2000
Sorghum bicolor
brenda
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
-
brenda
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)
-
brenda
Asano, Y.; Tamura, K.; Doi, N.; Ueatrongchit, T.; H-Kittikun, A.; Ohmiya, T.
Screening for new hydroxynitrilases from plants
Biosci. Biotechnol. Biochem.
69
2349-2357
2005
Baliospermum montanum
brenda
Hernandez, L.; Luna, H.; Ruiz-Teran, F.; Vazquez, A.
Screening for hydroxynitrile lyase activity in crude preparations of some edible plants
J. Mol. Catal. B
30
105-108
2004
Annona cherimola, Annona squamosa
-
brenda
Guterl, J.K.
Andexer, J.N.; Sehl, T.; von Langermann, J.; Frindi-Wosch, I.; Rosenkranz, T.; Fitter, J.; Gruber, K.; Kragl, U.; Eggert, T.; Pohl, M.: Uneven twins: comparison of two enantiocomplementary hydroxynitrile lyases with alpha/beta-hydrolase fold
J. Biotechnol.
141
166-173
2009
Manihot esculenta
brenda
EXTERNAL LINKS (specific for EC-Number 4.1.2.11)
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