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Literature summary for 1.4.1.18 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
Search for more literature for 1.4.1.18

Crystallization (Commentary)

Crystallization (Comment) Organism
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

Protein Variants Comment Organism
F173A mutation creates an additional large hydrophobic binding pocket in the active site, which favours the binding of aromatic substrates Geobacillus stearothermophilus
F173G very low level of activity towards the tested substrates Geobacillus stearothermophilus
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
R242M/F173A mutant converts substrates 1-phenylethan-1-one (6%) and 1-phenylpropan-1-one (19%, ee > 99% R) Geobacillus stearothermophilus
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
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
V130A/F173V inactive Geobacillus stearothermophilus
V130G/F173A mutant is stereospecific (ee > 99% R) for the amination of 1-phenylpropan-1-one (78% conversion) and other ketones Geobacillus stearothermophilus
V130G/F173V inactive Geobacillus stearothermophilus
V172A/F173A dramatic reduction of catalytic activity Geobacillus stearothermophilus
V172A/F173G very low level of activity towards the tested substrates Geobacillus stearothermophilus
V172G/F173A dramatic reduction of catalytic activity Geobacillus stearothermophilus
V172G/F173G very low level of activity towards the tested substrates Geobacillus stearothermophilus

Organism

Organism UniProt Comment Textmining
Geobacillus stearothermophilus Q9AJC6
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
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
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 ?
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
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 ?
1-phenylpentan-1-one + NADH + H+ + NH3 mutant F173A, 10 mM, 36% conversion Geobacillus stearothermophilus 1-phenylpentan-1-amine + NAD+ + H2O
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 ?
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
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 ?
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
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 ?
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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 ?
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
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 ?
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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 ?
6-oxohexanoic acid + NADH + H+ + NH3 mutant F173A, 10 mM, 99% conversion Geobacillus stearothermophilus L-lysine + NAD+ + H2O
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 ?
cyclohexanone + NADH + H+ + NH3 mutant F173A, 10 mM, 86% conversion Geobacillus stearothermophilus cyclohexanamine + NAD+ + H2O
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 ?
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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 ?
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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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
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 ?

Temperature Optimum [°C]

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

Temperature Stability [°C]

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

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
9
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-
 Geobacillus stearothermophilus