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Literature summary for 1.5.1.48 extracted from

  • Hussain, S.; Leipold, F.; Man, H.; Wells, E.; France, S.P.; Mulholland, K.R.; Grogan, G.; Turner, N.J.
    An (R)-imine reductase biocatalyst for the asymmetric reduction of cyclic imines (2015), ChemCatChem, 7, 579-583 .
    View publication on PubMedView publication on EuropePMC

Application

Application Comment Organism
synthesis (R)-imine reductase is a biocatalyst for the asymmetric reduction of cyclic imines Streptomyces sp. GF3587

Cloned(Commentary)

Cloned (Comment) Organism
recombinant overexpression in Escherichia coli Streptomyces sp. GF3587

Protein Variants

Protein Variants Comment Organism
D172A site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme and also reduced enantioselectivity depending on the substrate, overview Streptomyces sp. GF3587
D172K site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme and also reduced enantioselectivity depending on the substrate, overview Streptomyces sp. GF3587
additional information creation of a recombinant whole-cell biocatalyst for the asymmetric reduction of prochiral imines by recombinant overexpression of the (R)-imine reductase from Streptomyces sp. GF3587 in Escherichia coli Streptomyces sp. GF3587

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.155
-
1-methyl-3,4-dihydroisoquinoline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
0.244
-
6-(thiophen-2-yl)-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
0.317
-
3,4-dihydroisoquinoline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
0.371
-
6-methyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
0.481
-
2-methyl-3,4-dihydroisoquinolin-2-ium recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
0.804
-
6-propyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.05
-
6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.55
-
6-cyclohexyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.77
-
6-(prop-1-en-2-yl)-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.88
-
2-methyl-1-pyrroline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
5.22
-
6-phenyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2-methyl-1-pyrroline + NADPH + H+ Streptomyces sp. GF3587
-
(R)-2-methylpyrrolidine + NADP+
-
?

Organism

Organism UniProt Comment Textmining
Streptomyces sp. GF3587 M4ZRJ3
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1,2-dimethyl-3,4-dihydroisoquinolin-2-ium + NADPH + H+
-
Streptomyces sp. GF3587 (1R)-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline + NADP+
-
?
1-methyl-3,4-dihydroisoquinoline + NADPH + H+ over 98% enantiomeric excess Streptomyces sp. GF3587 (1R)-1-methyl-1,2,3,4-tetrahydroisoquinoline + NADP+
-
?
2-cyclohexyl-1-pyrroline + NADPH + H+ significant reduction in enantioselectivity is observed with this bulkier substituent compared to 2-methyl-1-pyrroline Streptomyces sp. GF3587 (2S)-2-cyclohexylpyrrolidine + NADP+
-
?
2-methyl-1-pyrroline + NADPH + H+
-
Streptomyces sp. GF3587 (R)-2-methylpyrrolidine + NADP+
-
?
2-methyl-1-pyrroline + NADPH + H+ enantioselective reaction, the enzyme produces only the (R)-isomer, conversion rate of over 98% and enantiomeric excess of also over 98% Streptomyces sp. GF3587 (R)-2-methylpyrrolidine + NADP+
-
?
2-methyl-3,4-dihydroisoquinolin-2-ium + NADPH + H+
-
Streptomyces sp. GF3587 2-methyl-1,2,3,4-tetrahydroisoquinoline + NADP+
-
?
2-phenyl-1-pyrroline + NADPH + H+
-
Streptomyces sp. GF3587 (2S)-2-phenylpyrrolidine + NADP+
-
?
2-phenyl-1-pyrroline + NADPH + H+ significant reduction in enantioselectivity is observed with this bulkier substituent compared to 2-methyl-1-pyrroline Streptomyces sp. GF3587 (2S)-2-phenylpyrrolidine + NADP+
-
?
3,4-dihydroisoquinoline + NADPH + H+
-
Streptomyces sp. GF3587 1,2,3,4-tetrahydroisoquinoline + NADP+
-
?
5-(4-fluorophenyl)-3,4-dihydro-2H-pyrrole + NADPH + H+
-
Streptomyces sp. GF3587 (2S)-2-(4-fluorophenyl)pyrrolidine + NADP+
-
?
5-(4-methoxyphenyl)-3,4-dihydro-2H-pyrrole + NADPH + H+
-
Streptomyces sp. GF3587 (2S)-2-(4-methoxyphenyl)pyrrolidine + NADP+
-
?
5-methyl-3,4-dihydro-2H-pyrrole + NADPH + H+
-
Streptomyces sp. GF3587 (2R)-2-methylpyrrolidine + NADP+
-
?
6-(2-methoxyphenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
-
Streptomyces sp. GF3587 (2S)-2-(2-methoxyphenyl)piperidine + NADP+
-
?
6-(3-methoxyphenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
-
Streptomyces sp. GF3587 (2S)-2-(3-methoxyphenyl)piperidine + NADP+
-
?
6-(4-fluorophenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
-
Streptomyces sp. GF3587 (2S)-2-(4-fluorophenyl)piperidine + NADP+
-
?
6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
-
Streptomyces sp. GF3587 (2S)-2-(4-methoxyphenyl)piperidine + NADP+
-
?
6-(4-methylphenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
-
Streptomyces sp. GF3587 (2S)-2-(4-methylphenyl)piperidine + NADP+
-
?
6-(naphthalen-2-yl)-2,3,4,5-tetrahydropyridine + NADPH + H+
-
Streptomyces sp. GF3587 (-)-2-(naphthalen-2-yl)piperidine + NADP+
-
?
6-(prop-1-en-2-yl)-2,3,4,5-tetrahydropyridine + NADPH + H+
-
Streptomyces sp. GF3587 (2S)-2-(prop-1-en-2-yl)piperidine + NADP+
-
?
6-(propan-2-yl)-2,3,4,5-tetrahydropyridine + NADPH + H+
-
Streptomyces sp. GF3587 (2S)-2-(propan-2-yl)piperidine + NADP+
-
?
6-(thiophen-2-yl)-2,3,4,5-tetrahydropyridine + NADPH + H+
-
Streptomyces sp. GF3587 (-)-2-(thiophen-2-yl)piperidine + NADP+
-
?
6-benzyl-2,3,4,5-tetrahydropyridine + NADPH + H+
-
Streptomyces sp. GF3587 (2S)-2-benzylpiperidine + NADP+
-
?
6-cyclohexyl-2,3,4,5-tetrahydropyridine + NADPH + H+
-
Streptomyces sp. GF3587 (-)-2-cyclohexylpiperidine + NADP+
-
?
6-methyl-2,3,4,5-tetrahydropyridine + NADPH + H+
-
Streptomyces sp. GF3587 (2R)-2-methylpiperidine + NADP+
-
?
6-phenyl-2,3,4,5-tetrahydropyridine + NADPH + H+
-
Streptomyces sp. GF3587 (2S)-2-phenylpiperidine + NADP+
-
?
6-propyl-2,3,4,5-tetrahydropyridine + NADPH + H+
-
Streptomyces sp. GF3587 (2R)-2-propylpiperidine + NADP+
-
?
additional information analysis of the enzyme substrate specificity, overview. Enzyme (R)-IRED catalyzes the reduction of pyrrolines containing both aliphatic and aromatic substituents at C-2. When a para-methoxy substituent is introduced on the benzene ring, conversion falls to 20% but the reaction proceeds with excellent selectivity to give (S)-2c in over 98% enantiomeric excess Streptomyces sp. GF3587 ?
-
?

Subunits

Subunits Comment Organism
More construction of a homology model of the enzyme active site, based on the structure of a closely related (R)-IRED from Streptomyces kanamyceticus Streptomyces sp. GF3587

Synonyms

Synonyms Comment Organism
(R)-imine reductase
-
Streptomyces sp. GF3587
(R)-IRED
-
Streptomyces sp. GF3587

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.0215
-
6-cyclohexyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
0.141
-
3,4-dihydroisoquinoline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
0.189
-
1-methyl-3,4-dihydroisoquinoline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
0.263
-
6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
0.351
-
2-methyl-1-pyrroline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
0.643
-
6-(thiophen-2-yl)-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.057
-
2-methyl-3,4-dihydroisoquinolin-2-ium recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
2.35
-
6-(prop-1-en-2-yl)-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
3.64
-
6-phenyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
4.21
-
6-methyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
4.63
-
6-propyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587

Cofactor

Cofactor Comment Organism Structure
NADPH
-
Streptomyces sp. GF3587

General Information

General Information Comment Organism
additional information construction of a homology model of the enzyme active site, based on the structure of a closely related (R)-IRED from Streptomyces kanamyceticus Streptomyces sp. GF3587

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.0139
-
6-cyclohexyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
0.187
-
2-methyl-1-pyrroline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
0.25
-
6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
0.447
-
3,4-dihydroisoquinoline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
0.698
-
6-phenyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.22
-
1-methyl-3,4-dihydroisoquinoline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.33
-
6-(prop-1-en-2-yl)-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
2.195
-
2-methyl-3,4-dihydroisoquinolin-2-ium recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
2.64
-
6-(thiophen-2-yl)-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
5.76
-
6-propyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
11.4
-
6-methyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587