Application | Comment | Organism |
---|---|---|
synthesis | (R)-imine reductase is a biocatalyst for the asymmetric reduction of cyclic imines | Streptomyces sp. GF3587 |
Cloned (Comment) | Organism |
---|---|
recombinant overexpression in Escherichia coli | Streptomyces sp. GF3587 |
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 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 | 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 | UniProt | Comment | Textmining |
---|---|---|---|
Streptomyces sp. GF3587 | M4ZRJ3 | - |
- |
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 | 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 | Comment | Organism |
---|---|---|
(R)-imine reductase | - |
Streptomyces sp. GF3587 |
(R)-IRED | - |
Streptomyces sp. GF3587 |
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 | Comment | Organism | Structure |
---|---|---|---|
NADPH | - |
Streptomyces sp. GF3587 |
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 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 |