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Information on EC 4.1.2.46 - aliphatic (R)-hydroxynitrile lyase
for references in articles please use BRENDA:EC4.1.2.46
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EC Tree 4 Lyases
4.1 Carbon-carbon lyases
4.1.2 Aldehyde-lyases
4.1.2.46 aliphatic (R)-hydroxynitrile lyase
IUBMB Comments
The enzyme contains Zn2+ . The enzyme catalyses the stereoselective synthesis of aliphatic (R)-cyanohydrins . No activity towards mandelonitrile and 4-hydroxymandelonitrile . Natural substrates for the (R)-oxynitrilase from Linum usitatissimum are acetone and butan-2-one, which are the building blocks of the cyanogen glycosides in Linum, linamarin and lotaustralin, or linustatin and neolinustatin, respectively .
The enzyme appears in viruses and cellular organisms
showSynonyms
(R)-HNL, (R)-hydroxynitrile lyase, (R)-Oxynitrilase, Acetone cyanohydrin lyase, EC 4.1.2.37, HNL, Hydroxynitrile lyase, LuHNL, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(R)-Oxynitrilase
Acetone cyanohydrin lyase
EC 4.1.2.37
-
-
formerly, part transferred
-
LuHNL
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2R)-2-hydroxy-2-methylbutanenitrile = cyanide + butan-2-one
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
linamarin degradation, linustatin bioactivation, lotaustralin degradation, neolinustatin bioactivation
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SYSTEMATIC NAME
IUBMB Comments
(2R)-2-hydroxy-2-methylbutanenitrile butan-2-one lyase (cyanide forming)
The enzyme contains Zn2+ [1]. The enzyme catalyses the stereoselective synthesis of aliphatic (R)-cyanohydrins [1]. No activity towards mandelonitrile and 4-hydroxymandelonitrile [5]. Natural substrates for the (R)-oxynitrilase from Linum usitatissimum are acetone and butan-2-one, which are the building blocks of the cyanogen glycosides in Linum, linamarin and lotaustralin, or linustatin and neolinustatin, respectively [4].
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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
(2R)-2-hydroxy-2-methylbutanenitrile
cyanide + 2-butanone
-
Substrates: -
Products: -
Products: -
?
(R)-2-butanone cyanohydrin
butan-2-one + cyanide
Substrates: -
Products: -
Products: -
r
(R)-mandelonitrile
cyanide + benzaldehyde
Substrates: -
Products: -
Products: -
?
3,3-dimethyl-2-butanone + acetone cyanohydrin
2-hydroxy-2,3,3-trimethylbutanenitrile + acetone
-
Substrates: -
Products: -
Products: -
?
acetone cyanohydrin
propan-2-one + cyanide
Substrates: -
Products: -
Products: -
r
acetyltrimethylsilane + acetone cyanohydrin
(R)-2-trimethylsilyl-2-hydroxy-ethylcyanide + acetone
-
Substrates: -
Products: enantioselective transcyanation. Under optimum conditions, both acetyltrimethylsilane conversion to (R)-2-trimethylsilyl-2-hydroxy-ethylcyanide and enantiomeric excess of the product are above 99%. The silicon atom in acetyltrimethylsilane has a great effect on the eaction and both the substrate conversion and the product enantiomeric excess are much higher than those in its carbon counterpart 3,3-dimethyl-2-butanone
Products: enantioselective transcyanation. Under optimum conditions, both acetyltrimethylsilane conversion to (R)-2-trimethylsilyl-2-hydroxy-ethylcyanide and enantiomeric excess of the product are above 99%. The silicon atom in acetyltrimethylsilane has a great effect on the eaction and both the substrate conversion and the product enantiomeric excess are much higher than those in its carbon counterpart 3,3-dimethyl-2-butanone
?
butan-2-one + cyanide
(R)-2-butanone cyanohydrin
Substrates: -
Products: -
Products: -
r
cyanide + 2-pentanone
(2R)-2-hydroxy-2-methylpentanenitrile
Substrates: 93% enantiomeric excess
Products: -
Products: -
?
cyanide + acrolein
(2R)-2-hydroxybut-3-enenitrile
Substrates: 74% enantiomeric excess
Products: -
Products: -
?
cyanide + butan-2-one
(2R)-butan-2-one cyanohydrin
Substrates: natural substrates for the (R)-oxynitrilase from Linum usitatissimum are acetone and butan-2-one, which are the building blocks of the cyanogen glycosides in Linum, linamarin and lotaustralin, or linustatin and neolinustatin, respectively
Products: -
Products: -
?
cyanide + chloroacetone
(2R)-3-chloro-2-hydroxy-2-methylpropionitrile
Substrates: -
Products: -
Products: -
?
cyanide + hexan-2-one
(2R)-2-hydroxy-2-methylhexanenitrile
Substrates: -
Products: -
Products: -
?
cyanide + hydroxyacetone
(2R)-1,2-dihydroxy-2-methyl-propane-3-nitrile
Substrates: -
Products: -
Products: -
?
cyanide + hydroxypivaldehyde
(2R)-2,4-dihydroxy-3,3-dimethylbutanenitrile
Substrates: 73% enantiomeric excess
Products: -
Products: -
?
cyanide + isobutyraldehyde
(2R)-2-hydroxy-4-methylpentanenitrile
Substrates: 93% enantiomeric excess
Products: -
Products: -
?
cyanide + methacrolein
(2R)-2-hydroxy-3-methylbut-3-enenitrile
Substrates: 98% enantiomeric excess
Products: -
Products: -
?
cyanide + methyl vinyl ketone
(2R)-2-hydroxy-2-methyl-3-butenenitrile
Substrates: -
Products: -
Products: -
?
cyanide + methyl vinyl ketone
(2R)-2-hydroxy-2-methylbut-3-enenitrile
Substrates: -
Products: despite a short reaction time of 0.8 h, the conversion of methyl vinyl ketone results in a poor (38%) enantiomeric excess value. As in the same time there is almost no conversion without enzyme. This compound is one of the rare examples, where the enzyme exerts only a partial stereoselectivity for a defined substrate
Products: despite a short reaction time of 0.8 h, the conversion of methyl vinyl ketone results in a poor (38%) enantiomeric excess value. As in the same time there is almost no conversion without enzyme. This compound is one of the rare examples, where the enzyme exerts only a partial stereoselectivity for a defined substrate
?
cyanide + pentan-2-one
(2R)-2-hydroxy-2-methylpentanenitrile
Substrates: -
Products: -
Products: -
?
cyanide + pinacolone
(2R)-2-hydroxy-2,3,3-trimethylbutyronitrile
Substrates: -
Products: -
Products: -
?
cyanide + pivalaldehyde
(2R)-3,3-dimethyl-2-hydroxybutyronitrile
Substrates: -
Products: -
Products: -
?
HCN + 4-hydroxybutanal
2,5-dihydroxypentanenitrile
-
Substrates: -
Products: -
Products: -
?
propan-2-one + cyanide
acetone cyanohydrin
Substrates: -
Products: -
Products: -
r
2-hydroxy-2-methylpropanenitrile
cyanide + acetone
-
Substrates: i.e. acetone cyanohydrin
Products: -
Products: -
?
2-hydroxy-2-methylpropanenitrile
cyanide + acetone
Substrates: the enzyme is involved in the catabolism of cyanogenic glycosides in young seedlings of Linum usitatissimum
Products: -
Products: -
?
cyanide + acetone
2-hydroxy-2-methylpropanenitrile
Substrates: natural substrates for the (R)-oxynitrilase from Linum usitatissimum are acetone and butan-2-one, which are the building blocks of the cyanogenic glycosides in Linum, linamarin and lotaustralin, or linustatin and neolinustatin, respectively
Products: -
Products: -
?
cyanide + acetone
2-hydroxy-2-methylpropanenitrile
Substrates: -
Products: -
Products: -
?
cyanide + butan-2-one
(2R)-2-hydroxy-2-methylbutanenitrile
Substrates: -
Products: -
Products: -
?
cyanide + butan-2-one
(2R)-2-hydroxy-2-methylbutanenitrile
Substrates: reaction with an immobilized form of the hydroxynitrile lyase as crosslinked enzyme aggregate with high specific activity and recovery on a preparative scale
Products: -
Products: -
?
cyanide + butan-2-one
(2R)-2-hydroxy-2-methylbutanenitrile
Substrates: -
Products: 77.2% enantiomeric excess
Products: 77.2% enantiomeric excess
?
cyanide + butan-2-one
(2R)-2-hydroxy-2-methylbutanenitrile
Substrates: 95% enantiomeric excess
Products: -
Products: -
?
cyanide + butyraldehyde
(2R)-2-hydroxypentanenitrile
Substrates: -
Products: -
Products: -
?
cyanide + butyraldehyde
(2R)-2-hydroxypentanenitrile
Substrates: 98% enantiomeric excess
Products: -
Products: -
?
cyanide + crotonaldehyde
(2R)-2-hydroxy-3-pentenenitrile
Substrates: -
Products: -
Products: -
?
cyanide + crotonaldehyde
(2R)-2-hydroxy-3-pentenenitrile
Substrates: 99% enantiomeric excess
Products: -
Products: -
?
cyanide + propionaldehyde
(2R)-2-hydroxybutyronitrile
Substrates: -
Products: -
Products: -
?
cyanide + propionaldehyde
(2R)-2-hydroxybutyronitrile
Substrates: 97% enantiomeric excess
Products: -
Products: -
?
additional information
?
-
-
Substrates: no activity with aromatic substrates
Products: -
Products: -
?
additional information
?
-
-
Substrates: no activity towards mandelonitrile and p-hydroxymandelonitrile
Products: -
Products: -
?
additional information
?
-
Substrates: the enzyme catalyzes the stereoselective synthesis of aliphatic (R)-cyanohydrins. Conversion of aromatic aldehydes (3-phenylpropionaldehyde or cinnamic aldehyde) and the aliphatic ketones is incomplete and gives poor enantiomeric excess-values, caused by the long reaction time
Products: -
Products: -
?
additional information
?
-
-
Substrates: synthesis of aromatic (S)-cyanohydrins. Most active towards derivatives of phenylacetone, converting 30-65% of the starting material to (S)-cyanohydrin with 55-95% enantiomeric excess in less than 1 day
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
(R)-mandelonitrile
cyanide + benzaldehyde
Substrates: -
Products: -
Products: -
?
cyanide + acetone
2-hydroxy-2-methylpropanenitrile
Substrates: natural substrates for the (R)-oxynitrilase from Linum usitatissimum are acetone and butan-2-one, which are the building blocks of the cyanogenic glycosides in Linum, linamarin and lotaustralin, or linustatin and neolinustatin, respectively
Products: -
Products: -
?
cyanide + butan-2-one
(2R)-butan-2-one cyanohydrin
Substrates: natural substrates for the (R)-oxynitrilase from Linum usitatissimum are acetone and butan-2-one, which are the building blocks of the cyanogen glycosides in Linum, linamarin and lotaustralin, or linustatin and neolinustatin, respectively
Products: -
Products: -
?
2-hydroxy-2-methylpropanenitrile
cyanide + acetone
-
Substrates: i.e. acetone cyanohydrin
Products: -
Products: -
?
2-hydroxy-2-methylpropanenitrile
cyanide + acetone
Substrates: the enzyme is involved in the catabolism of cyanogenic glycosides in young seedlings of Linum usitatissimum
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NAD+
an A-form NAD+ is tightly but not covalently bound to each subunit of the enzyme
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Zn2+
Zn2+
LuHNL has significant homologies to members of the Zn2+-containing alcohol dehydrogenases. In particular, residues responsible for coordination of Zn2+ ions or fulfilling structural or functional tasks in Zn2+-alcohol dehydrogenases are conserved. Contains about 2-4 mol zinc per mol of recombinant enzyme. Hydroxynitrile lyase from Linum usitatissimum and Zn2+-alcohol dehydrogenases have similar structural requirements with respect to maintaining a catalytically active structure. Residues essentially involved in catalysis of Zn2+-ADHs are also of functional importance in hydroxynitrile lyase from Linum usitatissimum
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
benzaldehyde
leads to a complete and irreversible deactivation of the enzyme within 2 h incubation
EDTA
84.4% residual activity after 2h at 30°C in the presence of 100 mM EDTA
additional information
-
no inhibition by 10 mM 2-mercaptoethanol, 1 mM iodoacetamide or iodoacetic acid, 10 mM isobutyronitrile or isopropanol
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
molecular imprinting using 2-butanone as additive in the immobilization process improves the synthetic activity of the biocatalyst
-
additional information
molecular imprinting using 2-butanone as additive in the immobilization process improves the synthetic activity of the biocatalyst
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
development of an immobilized form of the hydroxynitrile lyase as crosslinked enzyme aggregate (CLEA) with high specific activity (303.5 U/g) and recovery (33%), 180.5 U/g LuCLEA (crosslinked enzyme aggregate) (using sat. (NH4)2SO4), 9.9 U/g LuEA (Enzyme aggregate of LuHNL) (using sat. (NH4)2SO4), 110.9 U/g LuCLEA (using tert-butanol), 221.9 U/g LuEA (using tert-butanol)
additional information
development of an immobilized form of the hydroxynitrile lyase as crosslinked enzyme aggregate (CLEA) with high specific activity (303.5 U/g) and recovery (33%), 180.5 U/g LuCLEA (crosslinked enzyme aggregate) (using sat. (NH4)2SO4), 9.9 U/g LuEA (Enzyme aggregate of LuHNL) (using sat. (NH4)2SO4), 110.9 U/g LuCLEA (using tert-butanol), 221.9 U/g LuEA (using tert-butanol)
additional information
-
development of an immobilized form of the hydroxynitrile lyase as crosslinked enzyme aggregate with high specific activity (303.5 U/g) and recovery
additional information
development of an immobilized form of the hydroxynitrile lyase as crosslinked enzyme aggregate with high specific activity (303.5 U/g) and recovery
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5.5
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4.1 - 5.5
pH 4.1: about 70% of maximal activity, pH 5.5: maximal activity
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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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 detection level in cytoplasm, with lower levels in organelles, not detected in cell wall or vacuole
brenda
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). Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
ligand-free enzyme and its complex with acetone cyanohydrin and (R)-2-butanone cyanohydrin, sitting drop vapor diffusion method, using 0.1 M bis-Tris, pH 6.5, 20% (w/v) polyethylene glycol monomethyl ether 5000
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C265A
the mutant possesses approximately 80% activity compared with the wild type enzyme
E140A
the mutant possesses approximately 61% activity compared with the wild type enzyme
F340A
the mutant possesses approximately 5% activity compared with the wild type enzyme
K366A
the mutant possesses approximately 76% activity compared with the wild type enzyme
M74A
the mutant possesses approximately 8% activity compared with the wild type enzyme
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5
immobilization on Eupergit (carrier consisting of macroporous beads) improves the stability considerably in the pH range below pH 5
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
immobilization on Eupergit (carrier consisting of macroporous beads) improves the stability considerably in the pH range below pH 5
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
Ni Sepharose 6 column chromatography and Mono Q column chromatography
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
cloned into Pichia pastoris, expressed in Escherichia coli as an N-terminal hexa-histidine fusion protein
-
cloning of a myc-His-tagged LuHNL-cDNA under control of the methanol-inducible AOX1 (alcohol oxidase) promotor of Pichia pastoris and introduction in the SMD1168 strain. Recombinant LuHNL is kinetically indistinguishable from the authentic flax enzyme
expressed in Escherichia coli as N-terminal hexa-histidine fusion protein
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
-
optically active aliphatic omega-hydroxycyanohydrins are valued materials in organic synthesis
synthesis
-
production of organosilicon compounds by enantioselective transcyanation. Under optimum conditions, both acetyltrimethylsilane conversion to (R)-2-trimethylsilyl-2-hydroxy-ethylcyanide and enantiomeric excess of the product are above 99%. the silicon atom in acetyltrimethylsilane has a great effect on the eaction and both the substrate conversion and the product enantiomeric excess are much higher than those in its carbon counterpart 3,3-dimethyl-2-butanone
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Xu, L.L.; Singh, B.K.; Conn, E.E.
Purification and characterization of acetone cyanohydrin lyase from Linum usitatissimum
Arch. Biochem. Biophys.
263
256-263
1988
Linum usitatissimum
brenda
Albrecht, J.; Jansen, I.; Kula, M.R.
Improved purification of an (R)-oxynitrilase from Linum usitatissimum (flax) and investigation of the substrate range
Biotechnol. Appl. Biochem.
17
191-203
1993
Linum usitatissimum (P93243)
brenda
de Gonzalo, G.; Brieva, R.; Gotor, V.
(R)-Oxynitrilase-catalyzed transformation of omega-hydroxyalkanals
J. Mol. Catal. B
19-20
223-230
2002
Linum usitatissimum
-
brenda
Fechter, M.H.; Griengl, H.
Hydroxynitrile lyases: biological sources and application as biocatalysts
Food Technol. Biotechnol.
42
287-294
2004
Linum usitatissimum
-
brenda
Cabirol, F.L.; Tan, P.L.; Tay, B.; Cheng, S.; Hanefeld, U.; Sheldon, R.A.
Linum usitatissimum hydroxynitrile lyase cross-linked enzyme aggregates: a recyclable enantioselective catalyst
Adv. Synth. Catal.
350
2329-2338
2008
Linum usitatissimum, Linum usitatissimum (P93243)
-
brenda
Trummler, K.; Wajant, H.
Molecular cloning of acetone cyanohydrin lyase from flax (Linum usitatissimum). Definition of a novel class of hydroxynitrile lyases
J. Biol. Chem.
272
4770-4774
1997
Linum usitatissimum (P93243)
brenda
Breithaupt, H.; Pohl, M.; Bnigk, W.; Heim, P.; Schimz, K.-L.; Kula, M.-R.
Cloning and expression of (R)-hydroxynitrile lyase from Linum usitatissimum (flax)
J. Mol. Catal. B
6
315-332
1999
Linum usitatissimum (P93243)
-
brenda
Wajant, H.; Riedel, D.; Benz, S.; Mundry, K.-W.
Immunocytological localization of hydroxynitrile lyases from Sorghum bicolor L. and Linum usitatissimum L.
Plant Sci.
103
145-154
1994
Linum usitatissimum (P93243)
-
brenda
Trummler, K.; Roos, J.; Schwaneberg, U.; Effenberger, F.; Frster, S.; Pfizenmaier, K.; Wajant, H.
Expression of the Zn2+-containing hydroxynitrile lyase from flax (Linum usitatissimum) in Pichia pastoris - utilization of the recombinant enzyme for enzymatic analysis and site-directed mutagenesis
Plant Sci.
139
19-27
1998
Linum usitatissimum (P93243)
-
brenda
Roberge, D.; Fleitz, F.; Pollard, D.; Devine, P.
Synthesis of optically active cyanohydrins from aromatic ketones: evidence of an increased substrate range and inverted stereoselectivity for the hydroxynitrile lyase from Linum usitatissimum
Tetrahedron Asymmetry
18
208-214
2007
Linum usitatissimum
-
brenda
Liu, S.
Asymmetric synthesis of silicon containing (R)-ketone cyanhydrin catalyzed by (R)-hydroxynitrile lyase from peach seed meal
J. Shenzhen Univ. Sci. Eng.
28
54-59
2011
Prunus persica
-
brenda
Zheng, D.; Nakabayashi, M.; Asano, Y.
Structural characterization of Linum usitatissimum hydroxynitrile lyase A new cyanohydrin decomposition mechanism involving a cyano-zinc complex
J. Biol. Chem.
298
101650
2022
Linum usitatissimum (P93243)
brenda
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