Information on EC 2.1.1.115 - (RS)-1-benzyl-1,2,3,4-tetrahydroisoquinoline N-methyltransferase

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)

The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.1.1.115
-
RECOMMENDED NAME
GeneOntology No.
(RS)-1-benzyl-1,2,3,4-tetrahydroisoquinoline N-methyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
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
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
methyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Isoquinoline alkaloid biosynthesis
-
-
Biosynthesis of secondary metabolites
-
-
SYSTEMATIC NAME
IUBMB Comments
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.
CAS REGISTRY NUMBER
COMMENTARY hide
132084-82-3
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Berberis beaniana
-
-
-
Manually annotated by BRENDA team
Berberis bretschneideri
-
-
-
Manually annotated by BRENDA team
Berberis carminea
-
-
-
Manually annotated by BRENDA team
Berberis crataegina
-
-
-
Manually annotated by BRENDA team
Berberis henryana
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Berberis koetineana
3 isoenzymes: NMT-I, NMT-II, NMT-III
-
-
Manually annotated by BRENDA team
Berberis laxifolia
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Berberis stenophylla
-
-
-
Manually annotated by BRENDA team
V 29
-
-
Manually annotated by BRENDA team
Berberis taliensis
-
-
-
Manually annotated by BRENDA team
Atropurpurea
-
-
Manually annotated by BRENDA team
Berberis turcomanica
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Berberis wilsoniae
-
-
-
Manually annotated by BRENDA team
Bocconia cordata
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Corydalis vaginans
-
-
-
Manually annotated by BRENDA team
Glaucium corniculatum
-
-
-
Manually annotated by BRENDA team
Glaucium elegans
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Thalictrum dipterocarpum
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
S-Adenosyl-L-methionine + (R)-6-O-methylnorlaudanosoline
?
show the reaction diagram
Berberis koetineana
-
-
-
-
-
S-Adenosyl-L-methionine + (R)-norcoclaurine
?
show the reaction diagram
Berberis koetineana
-
-
-
-
-
S-Adenosyl-L-methionine + (R)-norprotosinomenine
?
show the reaction diagram
Berberis koetineana
-
isoenzyme NMT-I: 6% of maximal activity with (R)-tetrahydropapaverine
-
-
-
S-Adenosyl-L-methionine + (R,S)-4'-O-methylnorlaudanosoline
?
show the reaction diagram
Berberis koetineana
-
isoenzyme NMT-I: 3% of maximal activity with (R)-tetrahydropapaverine
-
-
-
S-Adenosyl-L-methionine + (R,S)-7-O-methylnorlaudanosoline
?
show the reaction diagram
Berberis koetineana
-
isoenzyme NMT-I: 12% of maximal activity with (R)-tetrahydropapaverine
-
-
-
S-Adenosyl-L-methionine + (R,S)-isococlaurine
?
show the reaction diagram
Berberis koetineana
-
-
-
-
-
S-Adenosyl-L-methionine + (R,S)-norarmepavine
?
show the reaction diagram
Berberis koetineana
-
-
-
-
-
S-Adenosyl-L-methionine + (R,S)-norcodamine
?
show the reaction diagram
Berberis koetineana
-
-
-
-
-
S-Adenosyl-L-methionine + (R,S)-nororientaline
?
show the reaction diagram
Berberis koetineana
-
-
-
-
-
S-Adenosyl-L-methionine + (RS)-1-benzyl-1,2,3,4-tetrahydroisoquinoline
?
show the reaction diagram
Berberis koetineana
-
-
-
-
-
S-Adenosyl-L-methionine + (S)-6-O-methylnorlaudanosoline
?
show the reaction diagram
Berberis koetineana
-
-
-
-
-
S-Adenosyl-L-methionine + (S)-norcoclaurine
?
show the reaction diagram
Berberis koetineana
-
-
-
-
-
S-Adenosyl-L-methionine + coclaurine
?
show the reaction diagram
Berberis koetineana
-
-
-
-
-
S-Adenosylmethionine + (R)-coclaurine
S-Adenosyl-L-homocysteine + N-methyl-(RS)-1-benzyl-1,2,3,4-tetrahydroisoquinoline
show the reaction diagram
Berberis koetineana
-
isoenzyme NMT-II and NMT-III show maximal activity with (R)-coclaurine
-
-
S-Adenosylmethionine + (R)-norreticuline
?
show the reaction diagram
Berberis koetineana
-
-
-
-
-
S-Adenosylmethionine + (R)-tetrahydropapaverine
?
show the reaction diagram
Berberis koetineana
-
isoenzyme NMT-I shows maximal activity with (R)-tetrahydropapaverine
-
-
-
S-Adenosylmethionine + (S)-coclaurine
S-Adenosylhomocysteine + N-methylcoclaurine
show the reaction diagram
Berberis koetineana
-
-
-
-
S-Adenosylmethionine + (S)-norreticuline
S-Adenosylhomocysteine + (S)-scoulerine
show the reaction diagram
Berberis koetineana
-
-
-
-
S-Adenosylmethionine + (S)-tetrahydropapaverine
?
show the reaction diagram
Berberis koetineana
-
-
-
-
-
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
S-Adenosyl-L-methionine + coclaurine
?
show the reaction diagram
Berberis koetineana
-
-
-
-
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.8
Berberis koetineana
-
isoenzyme NMT-III
7.4
Berberis koetineana
-
isoenzyme NMT-I and NMT-II
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
35 - 40
Berberis koetineana
-
isoenzyme NMT-I, NMT-II and NMT-III
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
Berberis koetineana
-
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60000
Berberis koetineana
-
isoenzyme NMT-I and NMT-III, gel filtration
68000
-
gel filtration
78000
Berberis koetineana
-
isoenzyme NMT-II, gel filtration
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6
Berberis koetineana
-
in presence of 20% glycerol, half-life of immobilized enzyme: 20 days
20
Berberis koetineana
-
in presence of 20% glycerol, half-life of immobilized enzyme: 7 days
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, in presence of 20% glycerol, half-life of immobilized enzyme: 40 days
Berberis koetineana
-
6°C, in presence of 20% glycerol, half-life of immobilized enzyme: 20 days
Berberis koetineana
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, in presence of 20% glycerol, half-life of immobilized enzyme: 40 days
Berberis koetineana
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
-
Berberis koetineana
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
Berberis koetineana
-
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