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IUBMB Comments Broad substrate specificity for (RS)-1-benzyl-1,2,3,4-tetrahydroisoquinolines; including coclaurine, norcoclaurine, isococlaurine, norarmepavine, norreticuline and tetrahydropapaverine. Both R- and S-enantiomers are methylated. The enzyme participates in the pathway leading to benzylisoquinoline alkaloid synthesis in plants. The physiological substrate is likely to be coclaurine. The enzyme was earlier termed norreticuline N-methyltransferase. However, norreticuline has not been found to occur in nature and that name does not reflect the broad specificity of the enzyme for (RS)-1-benzyl-1,2,3,4-tetrahydroisoquinolines.
The enzyme appears in viruses and cellular organisms
Synonyms
(R,S)-Tetrahydrobenzylisoquinoline-N-methyltransferase, Methyltransferase, tetrahydrobenzylisoquinoline, NMT, Norreticuline N-methyltransferase,
more
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(R,S)-Tetrahydrobenzylisoquinoline-N-methyltransferase
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Methyltransferase, tetrahydrobenzylisoquinoline
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Norreticuline N-methyltransferase
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S-adenosyl-L-methionine + (RS)-1-benzyl-1,2,3,4-tetrahydroisoquinoline = S-adenosyl-L-homocysteine + N-methyl-(RS)-1-benzyl-1,2,3,4-tetrahydroisoquinoline
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methyl group transfer
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S-adenosyl-L-methionine:(RS)-1-benzyl-1,2,3,4-tetrahydroisoquinoline N-methyltransferase
Broad substrate specificity for (RS)-1-benzyl-1,2,3,4-tetrahydroisoquinolines; including coclaurine, norcoclaurine, isococlaurine, norarmepavine, norreticuline and tetrahydropapaverine. Both R- and S-enantiomers are methylated. The enzyme participates in the pathway leading to benzylisoquinoline alkaloid synthesis in plants. The physiological substrate is likely to be coclaurine. The enzyme was earlier termed norreticuline N-methyltransferase. However, norreticuline has not been found to occur in nature and that name does not reflect the broad specificity of the enzyme for (RS)-1-benzyl-1,2,3,4-tetrahydroisoquinolines.
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S-Adenosyl-L-methionine + (R)-6-O-methylnorlaudanosoline
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Berberis koetineana
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?
S-Adenosyl-L-methionine + (R)-norcoclaurine
?
Berberis koetineana
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?
S-Adenosyl-L-methionine + (R)-norprotosinomenine
?
Berberis koetineana
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isoenzyme NMT-I: 6% of maximal activity with (R)-tetrahydropapaverine
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?
S-Adenosyl-L-methionine + (R,S)-4'-O-methylnorlaudanosoline
?
Berberis koetineana
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isoenzyme NMT-I: 3% of maximal activity with (R)-tetrahydropapaverine
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?
S-Adenosyl-L-methionine + (R,S)-7-O-methylnorlaudanosoline
?
Berberis koetineana
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isoenzyme NMT-I: 12% of maximal activity with (R)-tetrahydropapaverine
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?
S-Adenosyl-L-methionine + (R,S)-isococlaurine
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Berberis koetineana
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?
S-Adenosyl-L-methionine + (R,S)-norarmepavine
?
Berberis koetineana
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?
S-Adenosyl-L-methionine + (R,S)-norcodamine
?
Berberis koetineana
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?
S-Adenosyl-L-methionine + (R,S)-nororientaline
?
Berberis koetineana
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?
S-Adenosyl-L-methionine + (RS)-1-benzyl-1,2,3,4-tetrahydroisoquinoline
?
Berberis koetineana
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?
S-Adenosyl-L-methionine + (S)-6-O-methylnorlaudanosoline
?
Berberis koetineana
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?
S-Adenosyl-L-methionine + (S)-norcoclaurine
?
Berberis koetineana
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?
S-Adenosyl-L-methionine + coclaurine
?
Berberis koetineana
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?
S-Adenosylmethionine + (R)-coclaurine
S-Adenosyl-L-homocysteine + N-methyl-(RS)-1-benzyl-1,2,3,4-tetrahydroisoquinoline
Berberis koetineana
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isoenzyme NMT-II and NMT-III show maximal activity with (R)-coclaurine
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S-Adenosylmethionine + (R)-norreticuline
?
Berberis koetineana
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?
S-Adenosylmethionine + (R)-tetrahydropapaverine
?
Berberis koetineana
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isoenzyme NMT-I shows maximal activity with (R)-tetrahydropapaverine
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?
S-Adenosylmethionine + (S)-coclaurine
S-Adenosylhomocysteine + N-methylcoclaurine
Berberis koetineana
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?
S-Adenosylmethionine + (S)-norreticuline
S-Adenosylhomocysteine + (S)-scoulerine
Berberis koetineana
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?
S-Adenosylmethionine + (S)-tetrahydropapaverine
?
Berberis koetineana
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?
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S-Adenosyl-L-methionine + coclaurine
?
Berberis koetineana
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?
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0.004 - 0.05
(R)-6-O-methylnorlaudanosoline
0.012 - 0.018
(R)-norreticuline
0.0015 - 0.003
(S)-6-O-methylnorlaudanosoline
0.005 - 0.017
(S)-norreticuline
0.004
(R)-6-O-methylnorlaudanosoline
Berberis koetineana
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isoenzyme NMT-II
0.05
(R)-6-O-methylnorlaudanosoline
Berberis koetineana
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isoenzyme NMT-III
0.012
(R)-norreticuline
Berberis koetineana
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isoenzyme NMT-III
0.012
(R)-norreticuline
Berberis koetineana
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isoenzyme NMT-I
0.015
(R)-norreticuline
Berberis koetineana
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isoenzyme NMT-II
0.018
(R)-norreticuline
Berberis koetineana
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isoenzyme NMT-I
0.0015
(S)-6-O-methylnorlaudanosoline
Berberis koetineana
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isoenzyme NMT-III
0.003
(S)-6-O-methylnorlaudanosoline
Berberis koetineana
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isoenzyme NMT-II
0.005
(S)-norreticuline
Berberis koetineana
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isoenzyme NMT-III
0.005
(S)-norreticuline
Berberis koetineana
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isoenzyme NMT-I
0.009
(S)-norreticuline
Berberis koetineana
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isoenzyme NMT-II
0.017
(S)-norreticuline
Berberis koetineana
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isoenzyme NMT-I
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6.8
Berberis koetineana
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isoenzyme NMT-III
7.4
Berberis koetineana
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isoenzyme NMT-I and NMT-II
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35 - 40
Berberis koetineana
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isoenzyme NMT-I, NMT-II and NMT-III
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brenda
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brenda
Berberis beaniana
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brenda
Berberis bretschneideri
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brenda
Berberis carminea
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brenda
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brenda
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brenda
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brenda
Berberis henryana
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brenda
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brenda
Berberis koetineana
3 isoenzymes: NMT-I, NMT-II, NMT-III
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brenda
Berberis laxifolia
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brenda
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brenda
Berberis stenophylla
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brenda
V 29
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brenda
V 29
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brenda
Berberis taliensis
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brenda
Atropurpurea
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brenda
Berberis turcomanica
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brenda
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brenda
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brenda
Bocconia cordata
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brenda
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brenda
Corydalis vaginans
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brenda
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brenda
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brenda
Glaucium elegans
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
Thalictrum dipterocarpum
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brenda
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Berberis koetineana
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brenda
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Q948P7_COPJA
358
0
41781
TrEMBL
other Location (Reliability: 4 )
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60000
Berberis koetineana
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isoenzyme NMT-I and NMT-III, gel filtration
78000
Berberis koetineana
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isoenzyme NMT-II, gel filtration
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20
Berberis koetineana
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in presence of 20% glycerol, half-life of immobilized enzyme: 7 days
6
Berberis koetineana
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in presence of 20% glycerol, half-life of immobilized enzyme: 20 days
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-20°C, in presence of 20% glycerol, half-life of immobilized enzyme: 40 days
Berberis koetineana
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6°C, in presence of 20% glycerol, half-life of immobilized enzyme: 20 days
Berberis koetineana
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-20°C, in presence of 20% glycerol, half-life of immobilized enzyme: 40 days
Berberis koetineana
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synthesis
Berberis koetineana
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the enzyme immobilized on CH-Sepharose or CPG-10 glass beads is a useful tool for the preparative synthesis of isotopically labelled N-methylated benzylisoquinoline alkaloids
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Frenzel, T.; Zenk, M.H.
Purification and characterization of three isoforms of S-adenosyl-L-methionine: (R,S)-tetrahydrobenzylisoquinoline-N-methyltransferase from Berberis koetineana cell cultures
Phytochemistry
29
3491-3497
1990
Argemone platyceras, Berberis angulosa, Berberis thunbergii, Berberis beaniana, Berberis bretschneideri, Berberis carminea, Berberis crataegina, Berberis dictyophylla, Berberis gagnepainii, Berberis henryana, Berberis julianae, Berberis koetineana, Berberis laxifolia, Berberis stenophylla, Berberis stolonifera, Berberis taliensis, Berberis turcomanica, Berberis vulgaris, Berberis wilsoniae, Bocconia cordata, Coptis japonica, Corydalis vaginans, Eschscholzia californica, Glaucium corniculatum, Glaucium elegans, Glaucium flavum, Berberis nervosa, Sinopodophyllum hexandrum, Podophyllum peltatum, Stephania delavayi, Thalictrum dipterocarpum, Hyalosepalum caffrum, Berberis stolonifera V 29
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brenda
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