Literature summary for 1.4.3.12 extracted from

Wu, X.; Huang, Z.; Wang, Z.; Li, Z.; Wang, J.; Lin, J.; Chen, F.
Asymmetric synthesis of a key dextromethorphan intermediate and its analogues enabled by a new cyclohexylamine oxidase Enzyme Discov. React. Dev. Mechanistic Insight (2020), J. Org. Chem., 85, 5598-5614 .

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Application

Application	Comment	Organism
synthesis	stereoselective synthesis of various enantioenriched 1-benzyl-octahydroisoquinoline derivatives of potential pharmaceutical importance at a semipreparative scale	Erythrobacteraceae bacterium

Protein Variants

Protein Variants	Comment	Organism
F317A	kcat/Km for 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline is 30% of the wild-type value	Erythrobacteraceae bacterium
F327A	kcat/Km for 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline is 179% of the wild-type value	Erythrobacteraceae bacterium
G202A	kcat/Km for 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline is 298% of the wild-type value	Erythrobacteraceae bacterium
I173A	kcat/Km for 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline is 67% of the wild-type value	Erythrobacteraceae bacterium
I201A	kcat/Km for 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline is 24% of the wild-type value	Erythrobacteraceae bacterium
L200A	kcat/Km for 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline is 150% of the wild-type value	Erythrobacteraceae bacterium
L295A	kcat/Km for 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline is 30% of the wild-type value	Erythrobacteraceae bacterium
L295I	kcat/Km for 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline is 73% of the wild-type value	Erythrobacteraceae bacterium
P396A	kcat/Km for 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline is 1177% of the wild-type value	Erythrobacteraceae bacterium
T203A	kcat/Km for 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline is 63% of the wild-type value	Erythrobacteraceae bacterium

KM Value [mM]

KM Value [mM]	KM Value Maximum [mM]	Substrate	Comment	Organism	Structure
0.36	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme P396A	Erythrobacteraceae bacterium
0.52	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme F327A	Erythrobacteraceae bacterium
0.53	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme G202A	Erythrobacteraceae bacterium
0.61	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme L200A	Erythrobacteraceae bacterium
1.24	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme T203A	Erythrobacteraceae bacterium
1.84	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme I201A	Erythrobacteraceae bacterium
1.88	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme L295I	Erythrobacteraceae bacterium
2.13	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme F317A	Erythrobacteraceae bacterium
2.2	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, wild-type enzyme	Erythrobacteraceae bacterium
2.71	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme I173A	Erythrobacteraceae bacterium
6.54	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme L295A	Erythrobacteraceae bacterium

Organism

Organism	UniProt	Comment	Textmining
Erythrobacteraceae bacterium	-	-	-
Erythrobacteraceae bacterium CCH12-C2	-	-	-

Specific Activity [micromol/min/mg]

Specific Activity Minimum [µmol/min/mg]	Specific Activity Maximum [µmol/min/mg]	Comment	Organism
0.002	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, mutant enzyme W63A	Erythrobacteraceae bacterium
0.006	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, mutant enzyme L295Y	Erythrobacteraceae bacterium
0.007	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, mutant enzyme L174A	Erythrobacteraceae bacterium
0.009	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, mutant enzyme Y433A	Erythrobacteraceae bacterium
0.011	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, mutant enzyme Q208A	Erythrobacteraceae bacterium
0.015	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, mutant enzyme F342A	Erythrobacteraceae bacterium
0.016	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, mutant enzyme W325A	Erythrobacteraceae bacterium
0.053	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, mutant enzyme I201A	Erythrobacteraceae bacterium
0.074	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, mutant enzyme F317A	Erythrobacteraceae bacterium
0.089	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, mutant enzyme T203A	Erythrobacteraceae bacterium
0.09	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, mutant enzyme F327A	Erythrobacteraceae bacterium
0.116	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, mutant enzyme L200A	Erythrobacteraceae bacterium
0.152	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, mutant enzyme L295A	Erythrobacteraceae bacterium
0.166	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, mutant enzyme L295I	Erythrobacteraceae bacterium
0.177	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, mutant enzyme G202A	Erythrobacteraceae bacterium
0.194	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, mutant enzyme I173A	Erythrobacteraceae bacterium
0.26	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, wild-type enzyme	Erythrobacteraceae bacterium
0.461	-	substrate: 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, pH 7.5, 45°C, mutant enzyme P396A	Erythrobacteraceae bacterium

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline + + O2 + H2O	the enzyme is able to completely deracemize 100 mM 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline under Turner's deracemization conditions to afford (S)-1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline in 80% isolated yield and 99% nantiomeric excess at a semipreparative scale (0.4 mmol)	Erythrobacteraceae bacterium	?	-	?
1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline + + O2 + H2O	the enzyme is able to completely deracemize 100 mM 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline under Turner's deracemization conditions to afford (S)-1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline in 80% isolated yield and 99% nantiomeric excess at a semipreparative scale (0.4 mmol)	Erythrobacteraceae bacterium CCH12-C2	?	-	?

Synonyms

Synonyms	Comment	Organism
CHAOCCH12-C2	-	Erythrobacteraceae bacterium

Turnover Number [1/s]

Turnover Number Minimum [1/s]	Turnover Number Maximum [1/s]	Substrate	Comment	Organism	Structure
0.027	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme I201A	Erythrobacteraceae bacterium
0.039	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme F317A	Erythrobacteraceae bacterium
0.048	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme T203A	Erythrobacteraceae bacterium
0.056	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme L200A	Erythrobacteraceae bacterium
0.057	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme F327A	Erythrobacteraceae bacterium
0.084	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme L295I	Erythrobacteraceae bacterium
0.097	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme G202A	Erythrobacteraceae bacterium
0.111	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme I173A	Erythrobacteraceae bacterium
0.12	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme L295A	Erythrobacteraceae bacterium
0.135	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, wild-type enzyme	Erythrobacteraceae bacterium
0.26	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme P396A	Erythrobacteraceae bacterium

kcat/KM [mM/s]

kcat/KM Value [1/mMs^-1]	kcat/KM Value Maximum [1/mMs^-1]	Substrate	Comment	Organism	Structure
0.0147	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme I201A	Erythrobacteraceae bacterium
0.0183	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme F317A	Erythrobacteraceae bacterium
0.0183	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme L295A	Erythrobacteraceae bacterium
0.0387	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme T203A	Erythrobacteraceae bacterium
0.04	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme I173A	Erythrobacteraceae bacterium
0.0446	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme L295I	Erythrobacteraceae bacterium
0.06135	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, wild-type enzyme	Erythrobacteraceae bacterium
0.0918	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme L200A	Erythrobacteraceae bacterium
0.1096	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme F327A	Erythrobacteraceae bacterium
0.183	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme G202A	Erythrobacteraceae bacterium
0.722	-	1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline	pH 7.5, 45°C, mutant enzyme P396A	Erythrobacteraceae bacterium

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Release 2023.1 (January 2023)