1.5.1.48: 2-methyl-1-pyrroline reductase
This is an abbreviated version!
For detailed information about 2-methyl-1-pyrroline reductase, go to the full flat file.
Reaction
Synonyms
(R)-imine reductase, (R)-IRED, PlRIR
ECTree
1.5.1.48 2-methyl-1-pyrroline reductaseAdvanced search results
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Substrates Products on EC 1.5.1.48 - 2-methyl-1-pyrroline reductase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
1,2-dimethyl-3,4-dihydroisoquinolin-2-ium + NADPH + H+
(1R)-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline + NADP+
-
-
-
?
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
-
-
-
-
?
1-methyl-3,4-dihydroisoquinoline + NADPH + H+
(1R)-1-methyl-1,2,3,4-tetrahydroisoquinoline + NADP+
over 98% enantiomeric excess
-
-
?
1-methyl-3,4-dihydroisoquinoline + NADPH + H+
(1S)-1-methyl-1,2,3,4-tetrahydroisoquinoline + NADP+
-
-
-
-
?
2,3,3,5-tetramethyl-3H-indole + NADPH + H+
(2R)-2,3,3,5-tetramethyl-2,3-dihydro-1H-indole + NADP+
-
-
-
-
?
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
-
-
-
-
?
2,3,3-trimethyl-3H-indole + NADPH + H+
(2R)-2,3,3-trimethyl-2,3-dihydro-1H-indole + NADP+
-
-
-
-
?
2,3,3-trimethyl-5-(trifluoromethyl)-3H-indole + NADH + H+
(2R)-2,3,3-trimethyl-5-(trifluoromethyl)-2,3-dihydro-1H-indole + NADP+
-
-
-
-
?
2,3,3-trimethyl-5-nitro-3H-indole + NADPH + H+
(2R)-2,3,3-trimethyl-5-nitro-2,3-dihydro-1H-indole + NADP+
-
-
-
-
?
2,3,3-trimethylindolenine + NADPH + H+
(R)-2,3,3-trimethylindoline + NADP+
-
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+
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+
2-methyl-3,4-dihydroisoquinolin-2-ium + NADPH + H+
2-methyl-1,2,3,4-tetrahydroisoquinoline + NADP+
-
-
-
?
3,4-dihydroisoquinoline + NADPH + H+
1,2,3,4-tetrahydroisoquinoline + NADP+
-
-
-
?
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+
-
-
-
-
?
5-(4-fluorophenyl)-3,4-dihydro-2H-pyrrole + NADPH + H+
(2S)-2-(4-fluorophenyl)pyrrolidine + NADP+
-
-
-
?
5-(4-methoxyphenyl)-3,4-dihydro-2H-pyrrole + NADPH + H+
(2S)-2-(4-methoxyphenyl)pyrrolidine + NADP+
-
-
-
?
5-bromo-2,3,3-trimethyl-3H-indole + NADPH + H+
(2R)-5-bromo-2,3,3-trimethyl-2,3-dihydro-1H-indole + NADP+
-
-
-
-
?
5-chloro-2,3,3-trimethyl-3H-indole + NADPH + H+
(2R)-5-chloro-2,3,3-trimethyl-2,3-dihydro-1H-indole + NADP+
-
-
-
-
?
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
-
-
-
-
?
5-fluoro-2,3,3-trimethyl-3H-indole + NADPH + H+
(2S)-2-phenylpyrrolidine + NADP+
-
-
-
-
?
5-methoxy-2,3,3-trimethyl-3H-indole + NADPH + H+
(2R)-5-methoxy-2,3,3-trimethyl-2,3-dihydro-1H-indole + NADP+
-
-
-
-
?
5-methyl-3,4-dihydro-2H-pyrrole + NADPH + H+
(2R)-2-methylpyrrolidine + NADP+
-
-
-
?
6-(2-methoxyphenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-(2-methoxyphenyl)piperidine + NADP+
-
-
-
?
6-(3-methoxyphenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-(3-methoxyphenyl)piperidine + NADP+
-
-
-
?
6-(4-fluorophenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-(4-fluorophenyl)piperidine + NADP+
-
-
-
?
6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-(4-methoxyphenyl)piperidine + NADP+
-
-
-
?
6-(4-methylphenyl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-(4-methylphenyl)piperidine + NADP+
-
-
-
?
6-(naphthalen-2-yl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(-)-2-(naphthalen-2-yl)piperidine + NADP+
-
-
-
?
6-(prop-1-en-2-yl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-(prop-1-en-2-yl)piperidine + NADP+
-
-
-
?
6-(propan-2-yl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-(propan-2-yl)piperidine + NADP+
-
-
-
?
6-(thiophen-2-yl)-2,3,4,5-tetrahydropyridine + NADPH + H+
(-)-2-(thiophen-2-yl)piperidine + NADP+
-
-
-
?
6-benzyl-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-benzylpiperidine + NADP+
-
-
-
?
6-cyclohexyl-2,3,4,5-tetrahydropyridine + NADPH + H+
(-)-2-cyclohexylpiperidine + NADP+
-
-
-
?
6-methyl-2,3,4,5-tetrahydropyridine + NADPH + H+
(2R)-2-methylpiperidine + NADP+
-
-
-
?
6-methyl-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-methylpiperidine + NADP+
-
-
-
-
?
6-phenyl-2,3,4,5-tetrahydropyridine + NADPH + H+
(2S)-2-phenylpiperidine + NADP+
-
-
-
?
6-propyl-2,3,4,5-tetrahydropyridine + NADPH + H+
(2R)-2-propylpiperidine + NADP+
-
-
-
?
2-methyl-1-pyrroline + NADPH + H+
(R)-2-methylpyrrolidine + (S)-2-methylpyrrolidine + NADP+
-
-
the enzyme produces 27.5 mM (S)-2-methylpyrrolidine (92.3% e.e.) from 30 mM 2-methyl-1-pyrroline at 92.3% conversion in the presence of 2% (w/v) L-glucose after 72 h incubation, the enzyme produces 91 mM (R)-2-methylpyrrolidine with 99.2% e.e. and 27.5 mM (S)-2-methylpyrrolidine (92.3% e.e.) from 100 mM 2-methyl-1-pyrroline at 9192% conversion in the presence of 2% (w/v) L-glucose, respectively, after 84 h incubation
-
?
2-methyl-1-pyrroline + NADPH + H+
(R)-2-methylpyrrolidine + (S)-2-methylpyrrolidine + NADP+
-
-
the enzyme produces 27.5 mM (S)-2-methylpyrrolidine (92.3% e.e.) from 30 mM 2-methyl-1-pyrroline at 92.3% conversion in the presence of 2% (w/v) L-glucose after 72 h incubation, the enzyme produces 91 mM (R)-2-methylpyrrolidine with 99.2% e.e. and 27.5 mM (S)-2-methylpyrrolidine (92.3% e.e.) from 100 mM 2-methyl-1-pyrroline at 9192% conversion in the presence of 2% (w/v) L-glucose, respectively, after 84 h incubation
-
?
2-methyl-1-pyrroline + NADPH + H+
(R)-2-methylpyrrolidine + NADP+
-
-
-
-
?
2-methyl-1-pyrroline + NADPH + H+
(R)-2-methylpyrrolidine + NADP+
-
the enzyme is very specific for 2-methyl-1-pyrroline as substrate. The purified enzyme catalyzes the formation of (R)-2-methylpyrrolidine with 99% enantiomeric excess. The enzyme shows also oxidation activity for (R)-2-methyl-1-pyrroline under alkaline pH (10-11.5) conditions. No activity with (S)-2-methylpyrrolidine. No activity with NADH
-
-
r
2-methyl-1-pyrroline + NADPH + H+
(R)-2-methylpyrrolidine + NADP+
-
-
-
?
2-methyl-1-pyrroline + NADPH + H+
(R)-2-methylpyrrolidine + NADP+
enantioselective reaction, the enzyme produces only the (R)-isomer, conversion rate of over 98% and enantiomeric excess of also over 98%
-
-
?
2-phenyl-1-pyrroline + NADPH + H+
(2S)-2-phenylpyrrolidine + NADP+
-
-
-
?
2-phenyl-1-pyrroline + NADPH + H+
(2S)-2-phenylpyrrolidine + NADP+
significant reduction in enantioselectivity is observed with this bulkier substituent compared to 2-methyl-1-pyrroline
-
-
?
additional information
?
-
-
the purified recombinant enzyme PlRIR exhibits relatively high catalytic efficiency towards 2,3,3-trimethylindolenine. A panel of 3H-indoles and 3H-indole iodides are reduced by PlRIR to yield the corresponding products with high enantioselectivity of 66-98% enantiomeric excess. In addition, enzyme PlRIR also possesses good activities toward other types of imines such as pyrroline, tetrahydropyridine, and dihydroisoquinoline, indicating a reasonably broad substrate acceptance
-
-
?
additional information
?
-
-
no activity with DELTA1-pyrroline-2-carboxylate, methyl-DELTA1-pyrroline-2-carboxylate, dihydrofolate, DELTA1-piperidine-2-carboxylate, 1-methyl-3,4-dihydroisoquinoline, 1-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline, N-benzylidenebenzylamine, (E)-N-(1-phenylethylidene)benzeneamine ketone, 4-hydroxy-2-butanone, ethyl-3-oxobutanoate, ethyl 4-chloro-3-oxobutanoate, 3-2,2,6-trimethyl-2-cyclohexen-1,4-dione, 2-methylfuran, 2-methylimidazole, 2-methylthiazole, 2-methylpyrimidine, 2-methylpyrazine, 1,4,5,6-tetrahydropyrimidine
-
-
?
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
-
-
?
