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Literature summary extracted from

  • Tseliou, V.; Knaus, T.; Masman, M.F.; Corrado, M.L.; Mutti, F.G.
    Generation of amine dehydrogenases with increased catalytic performance and substrate scope from epsilon-deaminating L-Lysine dehydrogenase (2019), Nat. Commun., 10, 3717 .
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
1.4.1.18 molecular modeling of structure containing its natural substrate. Residues H181, Y238 and T240 appear to stabilize the alpha NH3+ group, whereas R242 appears to interact with the COO- of the substrate. Residues V172, F173 and V130 create a hindered hydrophobic environment Geobacillus stearothermophilus

Protein Variants

EC Number Protein Variants Comment Organism
1.4.1.18 F173A mutation creates an additional large hydrophobic binding pocket in the active site, which favours the binding of aromatic substrates Geobacillus stearothermophilus
1.4.1.18 F173G very low level of activity towards the tested substrates Geobacillus stearothermophilus
1.4.1.18 R242M residue R242 appears to be involved in the binding of the alpha-carboxylic group of L-lysine and is located at the entrance of the active site Geobacillus stearothermophilus
1.4.1.18 R242M/F173A mutant converts substrates 1-phenylethan-1-one (6%) and 1-phenylpropan-1-one (19%, ee > 99% R) Geobacillus stearothermophilus
1.4.1.18 R242M/F173V mutant converts substrates 1-phenylethan-1-one, 1-phenylpropan-1-one 1-phenylbutan-1-one and 2,3-dihydro-4H-1-benzopyran-4-one (38%, 41%, 8%, 15% conversions, ee > 99% R) Geobacillus stearothermophilus
1.4.1.18 V130A/F173A mutant exhibits a significant level of activity towards 1-phenylethan-1-one (74% conversion) and 1-phenylpropan-1-one (65% conversion), and all amine products are obtained in enantiomerically pure form (ee > 99% R) Geobacillus stearothermophilus
1.4.1.18 V130A/F173V inactive Geobacillus stearothermophilus
1.4.1.18 V130G/F173A mutant is stereospecific (ee > 99% R) for the amination of 1-phenylpropan-1-one (78% conversion) and other ketones Geobacillus stearothermophilus
1.4.1.18 V130G/F173V inactive Geobacillus stearothermophilus
1.4.1.18 V172A/F173A dramatic reduction of catalytic activity Geobacillus stearothermophilus
1.4.1.18 V172A/F173G very low level of activity towards the tested substrates Geobacillus stearothermophilus
1.4.1.18 V172G/F173A dramatic reduction of catalytic activity Geobacillus stearothermophilus
1.4.1.18 V172G/F173G very low level of activity towards the tested substrates Geobacillus stearothermophilus

Organism

EC Number Organism UniProt Comment Textmining
1.4.1.18 Geobacillus stearothermophilus Q9AJC6
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-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.4.1.18 1-phenylbutan-1-one + NADH + H+ + NH3 mutant F173A, 10 mM, 87% conversion, product in R-configuration, 99.8% ee Geobacillus stearothermophilus (1R)-1-phenylbutan-1-amine + NAD+ + H2O
-
 ?
1.4.1.18 1-phenylethan-1-one + NADH + H+ + NH3 mutant F173A, 10 mM, 99% conversion, product in R-configuration, 99.9% ee Geobacillus stearothermophilus (1R)-1-phenylethan-1-amine + NAD+ + H2O
-
 ?
1.4.1.18 1-phenylpentan-1-one + NADH + H+ + NH3 mutant F173A, 10 mM, 36% conversion Geobacillus stearothermophilus 1-phenylpentan-1-amine + NAD+ + H2O
-
 ?
1.4.1.18 1-phenylpropan-1-one + NADH + H+ + NH3 mutant F173A, 10 mM, 98% conversion, product in R-configuration, 99.9% ee Geobacillus stearothermophilus (1R)-1-phenylpropan-1-amine + NAD+ + H2O
-
 ?
1.4.1.18 2,3-dihydro-4H-1-benzopyran-4-one + NADH + H+ + NH3 mutant F173A, 10 mM, 82% conversion, product in R-configuration, 99.4% ee Geobacillus stearothermophilus (4R)-3,4-dihydro-2H-1-benzopyran-4-amine + NAD+ + H2O
-
 ?
1.4.1.18 3,4-dihydronaphthalen-1(2H)-one + NADH + H+ + NH3 mutant F173A, 10 mM, 79% conversion, product in R-configuration, 99% ee Geobacillus stearothermophilus (1R)-1,2,3,4-tetrahydronaphthalen-1-amine + NAD+ + H2O
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 ?
1.4.1.18 4-methylpentan-2-one + NADH + H+ + NH3 mutant F173A, 10 mM, 76% conversion, product in R-configuration, 97% ee Geobacillus stearothermophilus (2R)-4-methylpentan-2-amine + NAD+ + H2O
-
 ?
1.4.1.18 6-oxoheptanoic acid + NADH + H+ + NH3 mutant F173A, 10 mM, 99% conversion, product in S-configuration, 99% ee Geobacillus stearothermophilus (6S)-6-aminoheptanoic acid + NAD+ + H2O
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 ?
1.4.1.18 6-oxohexanoic acid + NADH + H+ + NH3 mutant F173A, 10 mM, 99% conversion Geobacillus stearothermophilus L-lysine + NAD+ + H2O
-
 ?
1.4.1.18 cyclohexanone + NADH + H+ + NH3 mutant F173A, 10 mM, 86% conversion Geobacillus stearothermophilus cyclohexanamine + NAD+ + H2O
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 ?
1.4.1.18 hexan-2-one + NADH + H+ + NH3 mutant F173A, 10 mM, 87% conversion, product in R-configuration, 99% ee Geobacillus stearothermophilus (2R)-hexan-2-amine + NAD+ + H2O
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 ?
1.4.1.18 additional information the alpha-carboxyl group is crucial for productive substrate binding and amination. No substrates: hexanal, heptanal, 2-heptanone, 2-octanone, acetophenone and alpha-chromanone Geobacillus stearothermophilus ?
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1.4.1.18 pentan-2-one + NADH + H+ + NH3 mutant F173A, 10 mM, 86% conversion, product in R-configuration, 89% ee Geobacillus stearothermophilus (2R)-pentan-2-amine + NAD+ + H2O
-
 ?

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.4.1.18 50
-
-
 Geobacillus stearothermophilus

Temperature Stability [°C]

EC Number Temperature Stability Minimum [°C] Temperature Stability Maximum [°C] Comment Organism
1.4.1.18 50
-
 stable for everal days Geobacillus stearothermophilus
1.4.1.18 69
-
 melting temperature Geobacillus stearothermophilus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.4.1.18 9
-
-
 Geobacillus stearothermophilus