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Literature summary extracted from

  • Costes, D.; Wehtje, E.; Adlercreutz, P.
    Hydroxynitrile lyase-catalyzed synthesis of cyanohydrins in organic solvents. Parameters influencing activity and enantiospecificity (1999), Enzyme Microb. Technol., 25, 384-391.
No PubMed abstract available

Activating Compound

EC Number Activating Compound Comment Organism Structure
4.1.2.47 dibutyl ether best solvent for HCN concentrations around 300 mM HCN concentration Hevea brasiliensis

Application

EC Number Application Comment Organism
4.1.2.11 synthesis biocatalyst for the enantiospecific addition of hydrogen cyanide to aldehydes in organic solvents Sorghum bicolor
4.1.2.47 synthesis biocatalyst for the enantiospecific addition of hydrogen cyanide to aldehydes in organic solvents Hevea brasiliensis
4.1.2.47 synthesis biocatalyst for the enantiospecific addition of hydrogen cyanide to aldehydes in organic solvents Manihot esculenta

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
4.1.2.47 additional information
-
 additional information
-
 Hevea brasiliensis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.1.2.11 cyanide + 4-hydroxybenzaldehyde Sorghum bicolor
-
 (S)-4-hydroxymandelonitrile
-
 r

Organism

EC Number Organism UniProt Comment Textmining
4.1.2.11 Sorghum bicolor
-
-
-
4.1.2.47 Hevea brasiliensis
-
-
-
4.1.2.47 Hevea brasiliensis
-
 rubber tree
-
4.1.2.47 Manihot esculenta
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.1.2.11 cyanide + 4-hydroxybenzaldehyde
-
 Sorghum bicolor (S)-4-hydroxymandelonitrile
-
 r
4.1.2.11 HCN + 3-phenylpropionaldehyde
-
 Sorghum bicolor 2-hydroxy-4-phenylbutanenitrile
-
 ?
4.1.2.11 HCN + 3-phenylpropionaldehyde
-
 Sorghum bicolor (2S)-2-hydroxy-4-phenylbutanenitrile 17% enantiomeric excess ?
4.1.2.11 HCN + 4-hydroxybenzaldehyde
-
 Sorghum bicolor (S)-4-hydroxymandelonitrile
-
 ?
4.1.2.11 HCN + acrolein
-
 Sorghum bicolor 2-hydroxybut-3-enenitrile
-
 ?
4.1.2.11 HCN + acrolein
-
 Sorghum bicolor (2S)-2-hydroxybut-3-enenitrile 25% enantiomeric excess ?
4.1.2.11 HCN + benzaldehyde
-
 Sorghum bicolor (S)-mandelonitrile
-
 ?
4.1.2.11 HCN + benzaldehyde
-
 Sorghum bicolor (S)-mandelonitrile 99% enantiomeric excess ?
4.1.2.11 additional information When the temperature decreases from 25°C to -5°C, the enantiomeric excess increases from 18% to 30% Sorghum bicolor ?
-
 ?
4.1.2.47 HCN + (benzyloxy)acetaldehyde
-
 Hevea brasiliensis 3-(benzyloxy)-(2S)-2-hydroxy-propanenitrile + 3-(benzyloxy)-(2R)-2-hydroxy-propanenitrile 50% 3-(benzyloxy)-(2S)-2-hydroxy-propanenitrile and 50% 3-(benzyloxy)-(2R)-2-hydroxy-propanenitrile ?
4.1.2.47 HCN + 2-naphthaldehyde
-
 Hevea brasiliensis (2S)-2-hydroxynaphthalen-2-yl-acetonitrile + (2R)-2-hydroxynaphthalen-2-yl-acetonitrile 83% (2S)-2-hydroxynaphthalen-2-yl-acetonitrile and 17% (2R)-2-hydroxynaphthalen-2-yl-acetonitrile ?
4.1.2.47 HCN + 2-naphthylacetaldehyde
-
 Hevea brasiliensis (2S)-2-hydroxy-3-naphthalen-1-yl-propionitrile + (2R)-2-hydroxy-3-naphthalen-1-yl-propionitrile 84.3% (2S)-2-hydroxy-3-naphthalen-1-yl-propionitrile and 15.6% (2R)-2-hydroxy-3-naphthalen-1-yl-propionitrile ?
4.1.2.47 HCN + 3-phenoxypropanal
-
 Hevea brasiliensis (2S)-2-hydroxy-4-phenoxybutanenitrile + (2S)-2-hydroxy-4-phenoxybutanenitrile 95.8% (2S)-2-hydroxy-4-phenoxybutanenitrile and 4.2% (2R)-2-hydroxy-4-phenoxybutanenitrile ?
4.1.2.47 HCN + 3-phenylpropionaldehyde
-
 Manihot esculenta (2S)-2-hydroxy-4-phenylbutanenitrile 67% enantiomeric excess ?
4.1.2.47 HCN + 3-phenylpropionaldehyde
-
 Hevea brasiliensis (2S)-2-hydroxy-4-phenylbutanenitrile 89% enantiomeric excess ?
4.1.2.47 HCN + acrolein
-
 Manihot esculenta (2S)-2-hydroxybut-3-enenitrile 59% enantiomeric excess ?
4.1.2.47 HCN + acrolein
-
 Hevea brasiliensis (2S)-2-hydroxybut-3-enenitrile 92% enantiomeric ecxess ?
4.1.2.47 HCN + benzaldehyde
-
 Hevea brasiliensis (S)-mandelonitrile 99% enantiomeric excess ?
4.1.2.47 HCN + benzaldehyde
-
 Manihot esculenta (S)-mandelonitrile 99% enantiomeric excess ?
4.1.2.47 additional information the enantiomeric excess of the product is optimal at pH 5.4 and at HCN concentration between 200 mM and 400 mM and clearly decreases at concentrations greater than 1.5 M. When the temperature decreases from 25°C to -5°C, the enantiomeric excess increases from 88% to 95% Hevea brasiliensis ?
-
 ?
4.1.2.47 additional information When the temperature decreases from 25°C to -5°C, the enantiomeric excess increases from 67% to 74% Manihot esculenta ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
4.1.2.11 (S)-Sb-HNL
-
 Sorghum bicolor
4.1.2.11 HNL
-
 Sorghum bicolor
4.1.2.11 Hydroxynitrile lyase
-
 Sorghum bicolor
4.1.2.47 (S)-Hb-HNL
-
 Hevea brasiliensis
4.1.2.47 (S)-Me-HNL
-
 Manihot esculenta
4.1.2.47 HNL
-
 Hevea brasiliensis
4.1.2.47 HNL
-
 Manihot esculenta
4.1.2.47 Hydroxynitrile lyase
-
 Hevea brasiliensis
4.1.2.47 Hydroxynitrile lyase
-
 Manihot esculenta

Temperature Range [°C]

EC Number Temperature Minimum [°C] Temperature Maximum [°C] Comment Organism
4.1.2.11 -5 25 when the temperature decreases from 25°C to -5°C, the enantiomeric excess increases from 18% to 30% Sorghum bicolor
4.1.2.47 -5 25 When the temperature decreases from 25°C to -5°C, the enantiomeric excess increases from 74% to 87% Manihot esculenta
4.1.2.47 -5 25 when the temperature decreases from 25°C to -5°C, the enantiomeric excess increases from 88% to 95% Hevea brasiliensis

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
4.1.2.47 5.4
-
 the enantiomeric excess is optimal Hevea brasiliensis

pH Stability

EC Number pH Stability pH Stability Maximum Comment Organism
4.1.2.47 5.4
-
 most stable at Hevea brasiliensis