4.1.2.46: aliphatic (R)-hydroxynitrile lyase
This is an abbreviated version!
For detailed information about aliphatic (R)-hydroxynitrile lyase, go to the full flat file.
Reaction
Synonyms
(R)-HNL, (R)-hydroxynitrile lyase, (R)-Oxynitrilase, Acetone cyanohydrin lyase, EC 4.1.2.37, Hydroxynitrile lyase, LuHNL
ECTree
4.1.2.46 aliphatic (R)-hydroxynitrile lyaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 4.1.2.46 - aliphatic (R)-hydroxynitrile lyase
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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
3,3-dimethyl-2-butanone + acetone cyanohydrin
2-hydroxy-2,3,3-trimethylbutanenitrile + acetone
-
-
-
-
?
acetyltrimethylsilane + acetone cyanohydrin
(R)-2-trimethylsilyl-2-hydroxy-ethylcyanide + acetone
-
-
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
-
?
cyanide + 2-pentanone
(2R)-2-hydroxy-2-methylpentanenitrile
93% enantiomeric excess
-
-
?
cyanide + acrolein
(2R)-2-hydroxybut-3-enenitrile
74% enantiomeric excess
-
-
?
cyanide + butan-2-one
(2R)-butan-2-one cyanohydrin
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
-
-
?
cyanide + chloroacetone
(2R)-3-chloro-2-hydroxy-2-methylpropionitrile
-
-
-
?
cyanide + hydroxyacetone
(2R)-1,2-dihydroxy-2-methyl-propane-3-nitrile
-
-
-
?
cyanide + hydroxypivaldehyde
(2R)-2,4-dihydroxy-3,3-dimethylbutanenitrile
73% enantiomeric excess
-
-
?
cyanide + isobutyraldehyde
(2R)-2-hydroxy-4-methylpentanenitrile
93% enantiomeric excess
-
-
?
cyanide + methacrolein
(2R)-2-hydroxy-3-methylbut-3-enenitrile
98% enantiomeric excess
-
-
?
cyanide + methyl vinyl ketone
(2R)-2-hydroxy-2-methyl-3-butenenitrile
-
-
-
?
cyanide + methyl vinyl ketone
(2R)-2-hydroxy-2-methylbut-3-enenitrile
-
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
-
-
-
?
cyanide + pinacolone
(2R)-2-hydroxy-2,3,3-trimethylbutyronitrile
-
-
-
?
cyanide + pivalaldehyde
(2R)-3,3-dimethyl-2-hydroxybutyronitrile
-
-
-
?
2-hydroxy-2-methylpropanenitrile
cyanide + acetone
-
i.e. acetone cyanohydrin
-
-
?
2-hydroxy-2-methylpropanenitrile
cyanide + acetone
the enzyme is involved in the catabolism of cyanogenic glycosides in young seedlings of Linum usitatissimum
-
-
?
cyanide + acetone
2-hydroxy-2-methylpropanenitrile
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
-
-
?
cyanide + butan-2-one
(2R)-2-hydroxy-2-methylbutanenitrile
-
-
-
?
cyanide + butan-2-one
(2R)-2-hydroxy-2-methylbutanenitrile
-
77.2% enantiomeric excess
-
?
cyanide + butan-2-one
(2R)-2-hydroxy-2-methylbutanenitrile
95% enantiomeric excess
-
-
?
cyanide + butan-2-one
(2R)-2-hydroxy-2-methylbutanenitrile
reaction with an immobilized form of the hydroxynitrile lyase as crosslinked enzyme aggregate with high specific activity and recovery on a preparative scale
-
-
?
cyanide + butyraldehyde
(2R)-2-hydroxypentanenitrile
98% enantiomeric excess
-
-
?
cyanide + crotonaldehyde
(2R)-2-hydroxy-3-pentenenitrile
99% enantiomeric excess
-
-
?
cyanide + propionaldehyde
(2R)-2-hydroxybutyronitrile
97% enantiomeric excess
-
-
?
additional information
?
-
-
no activity towards mandelonitrile and p-hydroxymandelonitrile
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
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
-
-
?
