Information on EC 1.5.1.48 - 2-methyl-1-pyrroline reductase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.5.1.48
-
RECOMMENDED NAME
GeneOntology No.
2-methyl-1-pyrroline reductase
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(R)-2-methylpyrrolidine + NADP+ = 2-methyl-1-pyrroline + NADPH + H+
show the reaction diagram
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
(R)-2-methylpyrrolidine:NADP+ 2-oxidoreductase
The enzyme from the bacterium Streptomyces sp. GF3587 is highly specific for its substrate and forms only the (R) isomer.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,1,2,3-tetramethyl-1H-benzo[e]indol-3-ium iodide + NADPH + H+
(-)-1,1,2,3-tetramethyl-2,3-dihydro-1H-benzo[e]indole + NADP+ + hydrogen iodide
show the reaction diagram
-
-
-
-
?
1,2,3,3,5-pentamethyl-3H-indol-1-ium iodide + NADPH + H+
(2S)-1,2,3,3,5-pentamethyl-2,3-dihydro-1H-indole + NADP+ + hydrogen iodide
show the reaction diagram
-
-
-
-
?
1,2,3,3-tetramethyl-3H-indol-1-ium iodide + NADPH + H+
(2S)-1,2,3,3-tetramethyl-2,3-dihydro-1H-indole + NADP+ + hydrogen iodide
show the reaction diagram
-
-
-
-
?
1,2-dimethyl-3,4-dihydroisoquinolin-2-ium + NADPH + H+
(1R)-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline + NADP+
show the reaction diagram
-
-
-
?
1-ethyl-2,3,3-trimethyl-3H-indol-1-ium iodide + NADPH + H+
(2S)-1-ethyl-2,3,3-trimethyl-2,3-dihydro-1H-indole + NADP+ + hydrogen iodide
show the reaction diagram
-
-
-
-
?
1-methyl-3,4-dihydroisoquinoline + NADPH + H+
(1R)-1-methyl-1,2,3,4-tetrahydroisoquinoline + NADP+
show the reaction diagram
over 98% enantiomeric excess
-
-
?
1-methyl-3,4-dihydroisoquinoline + NADPH + H+
(1S)-1-methyl-1,2,3,4-tetrahydroisoquinoline + NADP+
show the reaction diagram
-
-
-
-
?
2,3,3,5-tetramethyl-3H-indole + NADPH + H+
(2R)-2,3,3,5-tetramethyl-2,3-dihydro-1H-indole + NADP+
show the reaction diagram
-
-
-
-
?
2,3,3-trimethyl-1-propyl-3H-indol-1-ium iodide + NADPH + H+
(2S)-2,3,3-trimethyl-1-propyl-2,3-dihydro-1H-indole + NADP+ + hydrogen iodide
show the reaction diagram
-
-
-
-
?
2,3,3-trimethyl-3H-indole + NADPH + H+
(2R)-2,3,3-trimethyl-2,3-dihydro-1H-indole + NADP+
show the reaction diagram
-
-
-
-
?
2,3,3-trimethyl-5-(trifluoromethyl)-3H-indole + NADH + H+
(2R)-2,3,3-trimethyl-5-(trifluoromethyl)-2,3-dihydro-1H-indole + NADP+
show the reaction diagram
-
-
-
-
?
2,3,3-trimethyl-5-nitro-3H-indole + NADPH + H+
(2R)-2,3,3-trimethyl-5-nitro-2,3-dihydro-1H-indole + NADP+
show the reaction diagram
-
-
-
-
?
2,3,3-trimethylindolenine + NADPH + H+
(R)-2,3,3-trimethylindoline + NADP+
show the reaction diagram
-
conversion rate of over 81% and enantiomeric excess of also over 96% for the (R)-isomer
-
-
?
2-cyclohexyl-1-pyrroline + NADPH + H+
(2S)-2-cyclohexylpyrrolidine + NADP+
show the reaction diagram
significant reduction in enantioselectivity is observed with this bulkier substituent compared to 2-methyl-1-pyrroline
-
-
?
2-methyl-1-pyrroline + NADPH + H+
(R)-2-methylpyrrolidine + (S)-2-methylpyrrolidine + NADP+
show the reaction diagram
2-methyl-1-pyrroline + NADPH + H+
(R)-2-methylpyrrolidine + NADP+
show the reaction diagram
2-methyl-3,4-dihydroisoquinolin-2-ium + NADPH + H+
2-methyl-1,2,3,4-tetrahydroisoquinoline + NADP+
show the reaction diagram
-
-
-
?
2-phenyl-1-pyrroline + NADPH + H+
(2R)-5-fluoro-2,3,3-trimethyl-2,3-dihydro-1H-indole + NADP+
show the reaction diagram
-
-
-
-
?
2-phenyl-1-pyrroline + NADPH + H+
(2S)-2-phenylpyrrolidine + NADP+
show the reaction diagram
2methyl-1-pyrroline + NADPH + H+
(R)-2-methylpyrrolidine + NADP+
show the reaction diagram
-
-
-
-
?
3,4-dihydroisoquinoline + NADPH + H+
1,2,3,4-tetrahydroisoquinoline + NADP+
show the reaction diagram
-
-
-
?
4,6-difluoro-2,3,3-trimethyl-3H-indole + NADPH + H+
(2R)-4,6-difluoro-2,3,3-trimethyl-2,3-dihydro-1H-indole + NADP+
show the reaction diagram
-
-
-
-
?
5-(4-fluorophenyl)-3,4-dihydro-2H-pyrrole + NADPH + H+
(2S)-2-(4-fluorophenyl)pyrrolidine + NADP+
show the reaction diagram
-
-
-
?
5-(4-methoxyphenyl)-3,4-dihydro-2H-pyrrole + NADPH + H+
(2S)-2-(4-methoxyphenyl)pyrrolidine + NADP+
show the reaction diagram
-
-
-
?
5-bromo-2,3,3-trimethyl-3H-indole + NADPH + H+
(2R)-5-bromo-2,3,3-trimethyl-2,3-dihydro-1H-indole + NADP+
show the reaction diagram
-
-
-
-
?
5-chloro-2,3,3-trimethyl-3H-indole + NADPH + H+
(2R)-5-chloro-2,3,3-trimethyl-2,3-dihydro-1H-indole + NADP+
show the reaction diagram
-
-
-
-
?
5-fluoro-1,2,3,3-tetramethyl-3H-indol-1-ium iodide + NADPH + H+
(2S)-5-fluoro-1,2,3,3-tetramethyl-2,3-dihydro-1H-indole + NADP+ + hydrogen iodide
show the reaction diagram
-
-
-
-
?
5-methoxy-2,3,3-trimethyl-3H-indole + NADPH + H+
(2R)-5-methoxy-2,3,3-trimethyl-2,3-dihydro-1H-indole + NADP+
show the reaction diagram
-
-
-
-
?
5-methyl-3,4-dihydro-2H-pyrrole + NADPH + H+
(2R)-2-methylpyrrolidine + NADP+
show the reaction diagram
-
-
-
?
6-(2-methoxyphenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-(2-methoxyphenyl)piperidine + NADP+
show the reaction diagram
-
-
-
?
6-(3-methoxyphenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-(3-methoxyphenyl)piperidine + NADP+
show the reaction diagram
-
-
-
?
6-(4-fluorophenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-(4-fluorophenyl)piperidine + NADP+
show the reaction diagram
-
-
-
?
6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-(4-methoxyphenyl)piperidine + NADP+
show the reaction diagram
-
-
-
?
6-(4-methylphenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-(4-methylphenyl)piperidine + NADP+
show the reaction diagram
-
-
-
?
6-(naphthalen-2-yl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(-)-2-(naphthalen-2-yl)piperidine + NADP+
show the reaction diagram
-
-
-
?
6-(prop-1-en-2-yl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-(prop-1-en-2-yl)piperidine + NADP+
show the reaction diagram
-
-
-
?
6-(propan-2-yl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-(propan-2-yl)piperidine + NADP+
show the reaction diagram
-
-
-
?
6-(thiophen-2-yl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(-)-2-(thiophen-2-yl)piperidine + NADP+
show the reaction diagram
-
-
-
?
6-benzyl-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-benzylpiperidine + NADP+
show the reaction diagram
-
-
-
?
6-cyclohexyl-2,3,4,5-tetrahydropyridine + NADPH + H+
(-)-2-cyclohexylpiperidine + NADP+
show the reaction diagram
-
-
-
?
6-methyl-2,3,4,5-tetrahydropyridine + NADPH + H+
(2R)-2-methylpiperidine + NADP+
show the reaction diagram
-
-
-
?
6-methyl-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-methylpiperidine + NADP+
show the reaction diagram
-
-
-
-
?
6-phenyl-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-phenylpiperidine + NADP+
show the reaction diagram
-
-
-
?
6-propyl-2,3,4,5-tetrahydropyridine + NADPH + H+
(2R)-2-propylpiperidine + NADP+
show the reaction diagram
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
2-methyl-1-pyrroline + NADPH + H+
(R)-2-methylpyrrolidine + (S)-2-methylpyrrolidine + NADP+
show the reaction diagram
2-methyl-1-pyrroline + NADPH + H+
(R)-2-methylpyrrolidine + NADP+
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
-
1 mM, 78% inhibition
2,2'-bipyridyl
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1 mM, 75% inhibition
4-chloromercuribenzoate
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0.1 mM, 97% inhibition
8-hydroxyquinoline
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1 mM, 94% inhibition
AgNO3
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1 mM, 97% inhibition
CuCl2
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1 mM, 41% inhibition
Cuprizone
-
0.1 mM, 87% inhibition
HgCl2
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1 mM, 75% inhibition
PMSF
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0.1 mM, 93% inhibition
additional information
-
no inhibition: EDTA, Tiron, CaCl2, CdCl2, CoCl2, FeCl3, LiOH, MgCl2, NiCl2, ZnSO4, semicarbazide, diethylamine cysteamine, 3-(aminomethyl)pyridine, iodoacetate, (R)-(+)-cycloserine, diethyldithiocarbamiate, N-ethylmaleimide
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
L-Glucose
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130% activity in the presence of 2% (w/v) L-glucose
additional information
-
not activated by glycerol, sorbitol, or 2-propanal
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.155
1-methyl-3,4-dihydroisoquinoline
recombinant enzyme, pH and temperature not specified in the publication
1.88 - 3.52
2-methyl-1-pyrroline
0.481
2-methyl-3,4-dihydroisoquinolin-2-ium
recombinant enzyme, pH and temperature not specified in the publication
0.317
3,4-dihydroisoquinoline
recombinant enzyme, pH and temperature not specified in the publication
1.05
6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
1.77
6-(prop-1-en-2-yl)-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
0.244
6-(thiophen-2-yl)-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
1.55
6-cyclohexyl-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
0.371
6-methyl-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
-
5.22
6-phenyl-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
0.804
6-propyl-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
0.0037
NADPH
-
30C, pH 7.0
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.189
1-methyl-3,4-dihydroisoquinoline
recombinant enzyme, pH and temperature not specified in the publication
0.351
2-methyl-1-pyrroline
recombinant enzyme, pH and temperature not specified in the publication
1.057
2-methyl-3,4-dihydroisoquinolin-2-ium
recombinant enzyme, pH and temperature not specified in the publication
0.141
3,4-dihydroisoquinoline
recombinant enzyme, pH and temperature not specified in the publication
0.263
6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
2.35
6-(prop-1-en-2-yl)-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
0.643
6-(thiophen-2-yl)-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
0.0215
6-cyclohexyl-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
4.21
6-methyl-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
-
3.64
6-phenyl-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
4.63
6-propyl-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.22
1-methyl-3,4-dihydroisoquinoline
recombinant enzyme, pH and temperature not specified in the publication
1.58
2,3,3-trimethylindolenine
-
recombinant enzyme, pH 7.0, 30C
-
0.187
2-methyl-1-pyrroline
recombinant enzyme, pH and temperature not specified in the publication
2.195
2-methyl-3,4-dihydroisoquinolin-2-ium
recombinant enzyme, pH and temperature not specified in the publication
0.447
3,4-dihydroisoquinoline
recombinant enzyme, pH and temperature not specified in the publication
0.25
6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
1.33
6-(prop-1-en-2-yl)-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
2.64
6-(thiophen-2-yl)-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
0.0139
6-cyclohexyl-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
11.4
6-methyl-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
-
0.698
6-phenyl-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
5.76
6-propyl-2,3,4,5-tetrahydropyridine
recombinant enzyme, pH and temperature not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00032
-
30C, pH 7.0, oxidation of 2-methyl-1-pyrroline
10.2
-
30C, pH 7.0, reduction of 2-methyl-1-pyrroline
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5
-
reduction of 2-methyl-1-pyrroline
11
-
oxidation of (R)-2-methylpyrrolidine
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.2 - 8.7
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pH 6.2: about 35% of maximal activity, pH 8.7: about 55% of maximal activity, reduction of 2-methyl-1-pyrroline
10.2 - 11.7
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pH 6.2: about 60% of maximal activity, pH 8.7: about 60% of maximal activity, oxidation of (R)-2-methylpyrrolidine
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
32000
-
2 * 32000, SDS-PAGE
65000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
-
2 * 32000, SDS-PAGE
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
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
35
-
stable below, 30 min
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant N-terminally His-tagged enzyme from Escherichia coli strain BL21(DE3)
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant overexpression in Escherichia coli
recombinant overexpression of N-terminally His-tagged enzyme in Escherichia coli strain BL21(DE3)
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D172A
site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme and also reduced enantioselectivity depending on the substrate, overview
D172K
site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme and also reduced enantioselectivity depending on the substrate, overview
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
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
(R)-imine reductase is a biocatalyst for the asymmetric reduction of cyclic imines