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Information on EC 2.1.1.111 - anthranilate N-methyltransferase
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2.1.1.111 anthranilate N-methyltransferaseIUBMB Comments
Involved in the biosynthesis of acridine alkaloids in plant tissues.
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The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
ANMT, anthranilic acid N-methyltransferase, NMT, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
anthranilic acid N-methyltransferase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + anthranilate = S-adenosyl-L-homocysteine + N-methylanthranilate
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-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
methyl group transfer
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-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:anthranilate N-methyltransferase
Involved in the biosynthesis of acridine alkaloids in plant tissues.
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CAS REGISTRY NUMBER
COMMENTARY
123779-15-7
-
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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
S-adenosyl-L-methionine + methyl anthranilate
S-adenosyl-L-homocysteine + methyl N-methylanthranilate
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-
-
?
S-adenosyl-L-methionine + anthranilate
S-adenosyl-L-homocysteine + N-methylanthranilate
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-
-
-
?
S-adenosyl-L-methionine + anthranilate
S-adenosyl-L-homocysteine + N-methylanthranilate
-
first specific step in quinoline alkaloid biosynthesis
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-
?
S-adenosyl-L-methionine + anthranilate
S-adenosyl-L-homocysteine + N-methylanthranilate
-
-
-
-
?
S-adenosyl-L-methionine + anthranilate
S-adenosyl-L-homocysteine + N-methylanthranilate
-
-
-
?
S-adenosyl-L-methionine + anthranilate
S-adenosyl-L-homocysteine + N-methylanthranilate
-
first specific step in acridone alkaloid biosynthesis
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-
?
S-adenosyl-L-methionine + anthranilate
S-adenosyl-L-homocysteine + N-methylanthranilate
first specific step in acridone alkaloid biosynthesis
-
-
?
S-adenosyl-L-methionine + anthranilate
S-adenosyl-L-homocysteine + N-methylanthranilate
-
first specific step in quinoline alkaloid biosynthesis
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-
?
S-adenosyl-L-methionine + anthranilate
S-adenosyl-L-homocysteine + N-methylanthranilate
first specific step in alkaloid biosynthesis, substrate specificity determines the course of acridone biosynthesis
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-
?
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NATURAL SUBSTRATE
NATURAL 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
S-adenosyl-L-methionine + anthranilate
S-adenosyl-L-homocysteine + N-methylanthranilate
-
first specific step in quinoline alkaloid biosynthesis
-
-
?
S-adenosyl-L-methionine + anthranilate
S-adenosyl-L-homocysteine + N-methylanthranilate
-
first specific step in acridone alkaloid biosynthesis
-
-
?
S-adenosyl-L-methionine + anthranilate
S-adenosyl-L-homocysteine + N-methylanthranilate
first specific step in acridone alkaloid biosynthesis
-
-
?
S-adenosyl-L-methionine + anthranilate
S-adenosyl-L-homocysteine + N-methylanthranilate
-
first specific step in quinoline alkaloid biosynthesis
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Ca2+
73% relative enzyme activity in presence of 1.5 mM, significantly reduced
Co2+
activity reduced in presence of 1.5 mM, 25% relative activity retained
Mg2+
activity independent in presence of 1.5 mM of, 90% relative activity retained
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
in-gel digestion and peptide sequencing by mass spectrometry, Western Blot and phylogenetic analysis, assays conducted at 32°C in 73.5 mM glycine-NaOH buffer at pH 8.9, HPLC separation of assay extracts, list of compounds that are not accepted as substrate in assay
additional information
-
in-gel digestion and peptide sequencing by mass spectrometry, Western Blot and phylogenetic analysis, assays conducted at 32°C in 73.5 mM glycine-NaOH buffer at pH 8.9, HPLC separation of assay extracts, list of compounds that are not accepted as substrate in assay
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
8.2
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
32
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
crude extracts of total plants, elicited, 2 years old
brenda
central vascular bundles of, around cup-like structures in the outer ovary wall representing secretory oil glands
brenda
vascular region of secondary and primary shoots, moderate mRNA expression, high enzyme activity
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rhizodermis of older root parts, endodermis of younger root parts, high mRNA expression and enzyme activity
brenda
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). ANMT_RUTGR
364
0
40059
Swiss-Prot
other Location (Reliability: 1)
A0A396GSA2_MEDTR
125
0
14684
TrEMBL
other Location (Reliability: 4)
A0A396HGZ5_MEDTR
176
0
20120
TrEMBL
other Location (Reliability: 3)
Q2HTB5_MEDTR
375
0
41406
TrEMBL
other Location (Reliability: 1)
A0A513ZRX4_POLTB
123
0
13357
TrEMBL
Mitochondrion (Reliability: 5)
M4HXR6_9POAL
354
0
38657
TrEMBL
other Location (Reliability: 2)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
70000
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli, BL21 cells for induction of recombinant protein expression
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
expression of anthranilate N-methyltransferase, anthraniloyl-coenzyme A (CoA):methanol acyltransferase from Vitis labrusca, and anthranilate coenzyme A ligase from Pseudomonas aeruginosa in Escherichia coli mutants mutants (metJ, trpD, tyrR), which provide more anthranilate and/or S-adenosyl methionine, to synthesize N-methylanthranilate, methyl anthranilate, and methyl N-methylanthranilate. Approximately, 185.3 microM N-methylanthranilate and 95.2 microM methyl N-methylanthranilate are synthesized
synthesis
production of 4-hydroxycoumarin, 2,4-dihydroxyquinoline, and 4-hydroxy-1-methyl-2(1H)-quinolone in Escherichia coli using genes for the synthesis of salicylic acid from chorismate to supply the substrate for 4-hydroxycoumarin and the gene encoding N-methyltransferase for the synthesis of N-methylanthranilate from anthranilate. 255.4 mg/l 4-hydroxycoumarin, 753.7 mg/l dihydroxyquinoline, and 17.5 mg/l 4-hydroxy-1-methyl-2(1H)-quinolone are synthesized
synthesis
three anthranilate derivatives, N-methylanthranilate, methyl anthranilate, and methyl N-methylanthranilate are synthesized using metabolically engineered stains of Escherichia coli. NMT encoding N-methyltransferase from Ruta graveolens, AMAT encoding anthraniloyl-coenzyme A (CoA):methanol acyltransferase from Vitis labrusca, and pqsA encoding anthranilate coenzyme A ligase from Pseudomonas aeruginosa are cloned and Escherichia coli strains harboring these genes were used to synthesize the three desired compounds. Escherichia coli mutants (metJ, trpD, tyrR mutants), which provide more anthranilate and/or S-adenosyl methionine, are used to increase the production of the synthesized compounds. 0.1853 mM N-methylanthranilate and 0.0952 mM methyl N-methylanthranilate are synthesized
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Eilert, U.; Wolters B.
Elicitor induction of S-adenosyl-L-methionine: anthranilic acid N-methyltransferase activity in cell suspension and organ cultures of Ruta graveolens L.
Plant Cell Tissue Organ Cult.
18
1-18
1989
Ruta graveolens
-
brenda
Baumert, A.; Creche, J.; Rideau, M.; Chenieux, J.C.; Groeger, D.
Anthranilic acid-specific enzymes in alkaloid-producing tissue cultures of Choisya ternata and Ruta graveolens
Plant Physiol. Biochem.
28
587-592
1990
Choisya ternata, Ruta graveolens
-
brenda
Baumert, A.; Maier, W.; Schumann, B.; Gröger, D.
Increased accumulation of Acridone alkaloids by cell suspension cultures of Ruta graveolens in response to elicitors
J. Plant Physiol.
139
224-228
1991
Ruta graveolens
-
brenda
Maier, W; Baumert, A.; Groeger, D.
Partial purification and characterization of S-adenosyl-L-methionine:anthranilic acid N-methyltransferase from Ruta cell suspension cultures
J. Plant Physiol.
145
1-6
1995
Ruta graveolens
-
brenda
Rohde, B.; Hans, J.; Martens, S.; Baumert, A.; Hunziker, P.; Matern, U.
Anthranilate N-methyltransferase, a branch-point enzyme of acridone biosynthesis
Plant J.
53
541-553
2008
Ruta graveolens (A9X7L0), Ruta graveolens
brenda
Choo, H.J.; Ahn, J.H.
Synthesis of three bioactive aromatic compounds by introducing polyketide synthase genes into engineered Escherichia coli
J. Agric. Food Chem.
67
8581-8589
2019
Ruta graveolens (A9X7L0)
brenda
Lee, H.L.; Kim, S.Y.; Kim, E.J.; Han, D.Y.; Kim, B.G.; Ahn, J.H.
Synthesis of methylated anthranilate derivatives using engineered strains of Escherichia coli
J. Microbiol. Biotechnol.
29
839-844
2019
Ruta graveolens (A9X7L0)
brenda
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