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Literature summary 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

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

Cloned(Commentary)

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

Protein Variants

EC Number Protein Variants Comment Organism
1.5.1.48 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
1.5.1.48 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
1.5.1.48 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]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.5.1.48 0.155
-
 1-methyl-3,4-dihydroisoquinoline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 0.244
-
 6-(thiophen-2-yl)-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 0.317
-
 3,4-dihydroisoquinoline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 0.371
-
 6-methyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 0.481
-
 2-methyl-3,4-dihydroisoquinolin-2-ium recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 0.804
-
 6-propyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 1.05
-
 6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 1.55
-
 6-cyclohexyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 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
1.5.1.48 1.88
-
 2-methyl-1-pyrroline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 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)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.5.1.48 2-methyl-1-pyrroline + NADPH + H+ Streptomyces sp. GF3587
-
 (R)-2-methylpyrrolidine + NADP+
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.5.1.48 Streptomyces sp. GF3587 M4ZRJ3
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.5.1.48 1,2-dimethyl-3,4-dihydroisoquinolin-2-ium + NADPH + H+
-
 Streptomyces sp. GF3587 (1R)-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline + NADP+
-
 ?
1.5.1.48 1-methyl-3,4-dihydroisoquinoline + NADPH + H+ over 98% enantiomeric excess Streptomyces sp. GF3587 (1R)-1-methyl-1,2,3,4-tetrahydroisoquinoline + NADP+
-
 ?
1.5.1.48 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+
-
 ?
1.5.1.48 2-methyl-1-pyrroline + NADPH + H+
-
 Streptomyces sp. GF3587 (R)-2-methylpyrrolidine + NADP+
-
 ?
1.5.1.48 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+
-
 ?
1.5.1.48 2-methyl-3,4-dihydroisoquinolin-2-ium + NADPH + H+
-
 Streptomyces sp. GF3587 2-methyl-1,2,3,4-tetrahydroisoquinoline + NADP+
-
 ?
1.5.1.48 2-phenyl-1-pyrroline + NADPH + H+
-
 Streptomyces sp. GF3587 (2S)-2-phenylpyrrolidine + NADP+
-
 ?
1.5.1.48 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+
-
 ?
1.5.1.48 3,4-dihydroisoquinoline + NADPH + H+
-
 Streptomyces sp. GF3587 1,2,3,4-tetrahydroisoquinoline + NADP+
-
 ?
1.5.1.48 5-(4-fluorophenyl)-3,4-dihydro-2H-pyrrole + NADPH + H+
-
 Streptomyces sp. GF3587 (2S)-2-(4-fluorophenyl)pyrrolidine + NADP+
-
 ?
1.5.1.48 5-(4-methoxyphenyl)-3,4-dihydro-2H-pyrrole + NADPH + H+
-
 Streptomyces sp. GF3587 (2S)-2-(4-methoxyphenyl)pyrrolidine + NADP+
-
 ?
1.5.1.48 5-methyl-3,4-dihydro-2H-pyrrole + NADPH + H+
-
 Streptomyces sp. GF3587 (2R)-2-methylpyrrolidine + NADP+
-
 ?
1.5.1.48 6-(2-methoxyphenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
-
 Streptomyces sp. GF3587 (2S)-2-(2-methoxyphenyl)piperidine + NADP+
-
 ?
1.5.1.48 6-(3-methoxyphenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
-
 Streptomyces sp. GF3587 (2S)-2-(3-methoxyphenyl)piperidine + NADP+
-
 ?
1.5.1.48 6-(4-fluorophenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
-
 Streptomyces sp. GF3587 (2S)-2-(4-fluorophenyl)piperidine + NADP+
-
 ?
1.5.1.48 6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
-
 Streptomyces sp. GF3587 (2S)-2-(4-methoxyphenyl)piperidine + NADP+
-
 ?
1.5.1.48 6-(4-methylphenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
-
 Streptomyces sp. GF3587 (2S)-2-(4-methylphenyl)piperidine + NADP+
-
 ?
1.5.1.48 6-(naphthalen-2-yl)-2,3,4,5-tetrahydropyridine + NADPH + H+
-
 Streptomyces sp. GF3587 (-)-2-(naphthalen-2-yl)piperidine + NADP+
-
 ?
1.5.1.48 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+
-
 ?
1.5.1.48 6-(propan-2-yl)-2,3,4,5-tetrahydropyridine + NADPH + H+
-
 Streptomyces sp. GF3587 (2S)-2-(propan-2-yl)piperidine + NADP+
-
 ?
1.5.1.48 6-(thiophen-2-yl)-2,3,4,5-tetrahydropyridine + NADPH + H+
-
 Streptomyces sp. GF3587 (-)-2-(thiophen-2-yl)piperidine + NADP+
-
 ?
1.5.1.48 6-benzyl-2,3,4,5-tetrahydropyridine + NADPH + H+
-
 Streptomyces sp. GF3587 (2S)-2-benzylpiperidine + NADP+
-
 ?
1.5.1.48 6-cyclohexyl-2,3,4,5-tetrahydropyridine + NADPH + H+
-
 Streptomyces sp. GF3587 (-)-2-cyclohexylpiperidine + NADP+
-
 ?
1.5.1.48 6-methyl-2,3,4,5-tetrahydropyridine + NADPH + H+
-
 Streptomyces sp. GF3587 (2R)-2-methylpiperidine + NADP+
-
 ?
1.5.1.48 6-phenyl-2,3,4,5-tetrahydropyridine + NADPH + H+
-
 Streptomyces sp. GF3587 (2S)-2-phenylpiperidine + NADP+
-
 ?
1.5.1.48 6-propyl-2,3,4,5-tetrahydropyridine + NADPH + H+
-
 Streptomyces sp. GF3587 (2R)-2-propylpiperidine + NADP+
-
 ?
1.5.1.48 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

EC Number Subunits Comment Organism
1.5.1.48 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

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

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.5.1.48 0.0215
-
 6-cyclohexyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 0.141
-
 3,4-dihydroisoquinoline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 0.189
-
 1-methyl-3,4-dihydroisoquinoline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 0.263
-
 6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 0.351
-
 2-methyl-1-pyrroline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 0.643
-
 6-(thiophen-2-yl)-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 1.057
-
 2-methyl-3,4-dihydroisoquinolin-2-ium recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 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
1.5.1.48 3.64
-
 6-phenyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 4.21
-
 6-methyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 4.63
-
 6-propyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587

Cofactor

EC Number Cofactor Comment Organism Structure
1.5.1.48 NADPH
-
 Streptomyces sp. GF3587

General Information

EC Number General Information Comment Organism
1.5.1.48 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]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
1.5.1.48 0.0139
-
 6-cyclohexyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 0.187
-
 2-methyl-1-pyrroline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 0.25
-
 6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 0.447
-
 3,4-dihydroisoquinoline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 0.698
-
 6-phenyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 1.22
-
 1-methyl-3,4-dihydroisoquinoline recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 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
1.5.1.48 2.195
-
 2-methyl-3,4-dihydroisoquinolin-2-ium recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 2.64
-
 6-(thiophen-2-yl)-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 5.76
-
 6-propyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587
1.5.1.48 11.4
-
 6-methyl-2,3,4,5-tetrahydropyridine recombinant enzyme, pH and temperature not specified in the publication Streptomyces sp. GF3587