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Information on EC 2.1.1.158 - 7-methylxanthosine synthase
for references in articles please use BRENDA:EC2.1.1.158
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EC Tree 2 Transferases
2.1 Transferring one-carbon groups
2.1.1 Methyltransferases
2.1.1.158 7-methylxanthosine synthase
IUBMB Comments
The enzyme is specific for xanthosine, as XMP and xanthine cannot act as substrates [2,4]. The enzyme does not have N1- or N3- methylation activity . This is the first methylation step in the production of caffeine.
The enzyme appears in viruses and cellular organisms
- 2.1.1.158
-
histone-lysine
- histone
-
n-methylation
- methyltransferases
- phosphatidylcholine
-
euchromatic
- phosphatidylethanolamine
-
methylase
- phenylethanolamine
- s-adenosyl-l-homocysteine
-
prmts
- adomet
-
zeste
- coffea
- theobromine
- protein-arginine
-
s-adenosyl-l-methionine-dependent
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s-adenosylmethionine-dependent
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dimethylaminohydrolase
- phosphatidyl-n-monomethylethanolamine
- guanidinoacetate
- canephora
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ddahs
- agriculture
Reaction Schemes
showSynonyms
n-methyltransferase, xanthosine methyltransferase, cmxrs1, 7-n-methyltransferase, 7-methylxanthosine synthase, 7-methylxanthine synthase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
7-methylxanthosine synthase 1
CaXMT1
CmXRS1
xanthosine methyltransferase
XMT
XMT1
XRS1
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + xanthosine = S-adenosyl-L-homocysteine + 7-methylxanthosine
The enzyme is specific for xanthosine, as XMP and xanthine cannot act as substrates [2,4]. The enzyme does not have N1- or N3- methylation activity. This is the first methylation step in the production of caffeine.
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S-adenosyl-L-methionine + xanthosine = S-adenosyl-L-homocysteine + 7-methylxanthosine
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S-adenosyl-L-methionine + xanthosine = S-adenosyl-L-homocysteine + 7-methylxanthosine
a catalytic residue is Gln161, cosubstrate and substrate binding site structures involving the Ser316 for xanthosine recognition, overview
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PATHWAY SOURCE
PATHWAYS
MetaCyc
caffeine biosynthesis I, caffeine biosynthesis II (via paraxanthine), theobromine biosynthesis I
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:xanthosine N7-methyltransferase
The enzyme is specific for xanthosine, as XMP and xanthine cannot act as substrates [2,4]. The enzyme does not have N1- or N3- methylation activity [2]. This is the first methylation step in the production of caffeine.
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CAS REGISTRY NUMBER
COMMENTARY
192827-92-2
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
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Substrates: the enzyme is part of a caffeine biosynthetic pathway which includes a recycling of adenosine released from S-adenosyl-L-methionine in form of xanthosine monophosphate, overview
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
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Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: first step in caffeine biosynthesis pathway from xanthosine
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
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Substrates: in vivo feeding experiments with radio-labeled substrate, product determination, overview
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: step of the caffeine biosynthesis, caffeine accumulation in seeds
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: first step in caffeine biosynthesis pathway from xanthosine, reduction of the second enzyme of the pathway, 7-methylxanthine methyltransferase, EC 2.1.1.159, leads to reduced XMT1 expression
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
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Substrates: first step in caffeine biosynthesis pathway from xanthosine
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
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Substrates: first step in caffeine biosynthesis
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
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Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: the enzyme is specific for xanthosine
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
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Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
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Substrates: specific methylation at N-7 position
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
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Substrates: step of the caffeine biosynthesis, caffeine accumulation in seeds
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
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Substrates: first step in caffeine biosynthesis pathway from xanthosine, reduction of the second enzyme of the pathway, 7-methylxanthine methyltransferase, EC 2.1.1.159, leads to reduced XMT1 expression
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
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Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
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Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
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Substrates: step of the caffeine biosynthesis, caffeine accumulation in seeds
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
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Substrates: -
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additional information
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Substrates: substrate specificities of xanthine derivatives methyltransferases, overview. The recombinant GCS2 protein is not active with any xanthine derivative tested
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additional information
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Substrates: substrate specificities of xanthine derivatives methyltransferases, overview
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additional information
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Substrates: enzyme expression and activity during caffeine biosynthesis in fruits, overview
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additional information
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Substrates: substrate specificity of the recombinant His-tagged enzyme, no activity with xanthosine 5'-phosphate, theobromine, or 7-methylxanthosine
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additional information
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Substrates: substrate specificities of xanthine derivatives methyltransferases, overview
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additional information
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Substrates: enzyme expression and activity during caffeine biosynthesis in fruits, overview
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additional information
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Substrates: both xanthosine and its monoanionic form with N3 deprotonated are used as the substrates for the methylation. While the methyl group can be transferred to the monoanionic form of xanthosine with a reasonable free energy barrier (about 17 kcal/mol), this is not the case for the neutral xanthosine (barrier is about 31 kcal/mol). The hydrogen bonding and hydrophobic interactions involving the monoanionic form closely represent the corresponding interactions in the crystal structure, which seems not to be the case for the reactant complex involving the neutral xanthosine
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additional information
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Substrates: substrate specificity, overview. The enzyme is specific for 7-methylation of xanthosine
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additional information
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Substrates: substrate specificities of xanthine derivatives methyltransferases, overview
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additional information
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Substrates: enzyme expression and activity during caffeine biosynthesis in fruits, overview
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additional information
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Substrates: 7-methylxanthosine synthase shows the most critical substrate specifi city of the three types of N-methyltransferases in Coffea species
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
-
Substrates: the enzyme is part of a caffeine biosynthetic pathway which includes a recycling of adenosine released from S-adenosyl-L-methionine in form of xanthosine monophosphate, overview
Products: -
Products: -
?
S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
Products: -
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?
S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: first step in caffeine biosynthesis pathway from xanthosine
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ir
S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
-
Substrates: in vivo feeding experiments with radio-labeled substrate, product determination, overview
Products: -
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ir
S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
Products: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: step of the caffeine biosynthesis, caffeine accumulation in seeds
Products: -
Products: -
?
S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: first step in caffeine biosynthesis pathway from xanthosine, reduction of the second enzyme of the pathway, 7-methylxanthine methyltransferase, EC 2.1.1.159, leads to reduced XMT1 expression
Products: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
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Substrates: first step in caffeine biosynthesis pathway from xanthosine
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?
S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
-
Substrates: first step in caffeine biosynthesis
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
Products: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
-
Substrates: step of the caffeine biosynthesis, caffeine accumulation in seeds
Products: -
Products: -
?
S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
-
Substrates: first step in caffeine biosynthesis pathway from xanthosine, reduction of the second enzyme of the pathway, 7-methylxanthine methyltransferase, EC 2.1.1.159, leads to reduced XMT1 expression
Products: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
Products: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
Substrates: -
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S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
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Substrates: step of the caffeine biosynthesis, caffeine accumulation in seeds
Products: -
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?
S-adenosyl-L-methionine + xanthosine
S-adenosyl-L-homocysteine + 7-methylxanthosine
-
Substrates: -
Products: -
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?
additional information
?
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Substrates: enzyme expression and activity during caffeine biosynthesis in fruits, overview
Products: -
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?
additional information
?
-
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Substrates: enzyme expression and activity during caffeine biosynthesis in fruits, overview
Products: -
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additional information
?
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Substrates: enzyme expression and activity during caffeine biosynthesis in fruits, overview
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Asthma
Biochemical studies of N-methyltransferase in human and guinea-pig lung: no apparent role in the pathogenesis of asthma.
Asthma
No association of histamine- N-methyltransferase polymorphism with asthma or bronchial hyperresponsiveness in two German pediatric populations.
Asthma
[Expression of protein arginine N-methyltransferases in E3 rat models of acute asthma.]
Brachydactyly
Novel PRMT7 mutation in a rare case of dysmorphism and intellectual disability.
Breast Neoplasms
FOXA1 Directs H3K4 Monomethylation at Enhancers via Recruitment of the Methyltransferase MLL3.
Breast Neoplasms
Inhibition of euchromatin histone-lysine N-methyltransferase 2 sensitizes breast cancer cells to tumor necrosis factor-related apoptosis-inducing ligand through reactive oxygen species-mediated activating transcription factor 4-C/EBP homologous protein-death receptor 5 pathway activation.
Carcinogenesis
Aberrant Activity of Histone-Lysine N-Methyltransferase 2 (KMT2) Complexes in Oncogenesis.
Carcinogenesis
Downregulation of histone-lysine N-methyltransferase EZH2 inhibits cell viability and enhances chemosensitivity in lung cancer cells.
Carcinogenesis
Genomic alterations in KMT2 family predict outcome of immune checkpoint therapy in multiple cancers.
Carcinogenesis
In Vivo Genetic Screens of Patient-Derived Tumors Revealed Unexpected Frailty of the Transformed Phenotype.
Carcinogenesis
Molecular signature of interleukin-22 in colon carcinoma cells and organoid models.
Carcinogenesis
Myelocytomatosis-Protein Arginine N-Methyltransferase 5 Axis Defines the Tumorigenesis and Immune Response in Hepatocellular Carcinoma.
Carcinogenesis
Reduced expression of SETD2 and SNX9 proteins in chemically induced mammary tumorigenesis in Wistar rats: a prognostic histological and proteomic study.
Carcinoma
Molecular signature of interleukin-22 in colon carcinoma cells and organoid models.
Carcinoma, Hepatocellular
Elevated N-methyltransferase expression induced by hepatic stellate cells contributes to the metastasis of hepatocellular carcinoma via regulation of the CD44v3 isoform.
Carcinoma, Hepatocellular
Myelocytomatosis-Protein Arginine N-Methyltransferase 5 Axis Defines the Tumorigenesis and Immune Response in Hepatocellular Carcinoma.
Carcinoma, Hepatocellular
Protein arginine N-methyltransferase 1 promotes the proliferation and metastasis of hepatocellular carcinoma cells.
Carcinoma, Hepatocellular
[Comparison of the expression and activity of phosphatidylethanolamine N-methyltransferase 2 between primary cultured hepatocytes and hepatoma cells in rats]
Colitis
Protein Arginine Methyltransferase 5 Inhibition Upregulates Foxp3(+) Regulatory T Cells Frequency and Function during the Ulcerative Colitis.
Colorectal Neoplasms
Histone-lysine N-methyltransferase SETD7 is a potential serum biomarker for colorectal cancer patients.
Coronary Artery Disease
Association of the histone-lysine N-methyltransferase MLL5 gene with coronary artery disease in Chinese Han people.
Diabetic Retinopathy
Proteomic analysis of retinopathy-related plasma biomarkers in diabetic patients.
Hearing Loss, Sensorineural
Studying the Association between Sudden Hearing Loss and DNA N-Methyltransferase 1 (DNMT1) Genetic Polymorphism.
Hearing Loss, Sudden
Studying the Association between Sudden Hearing Loss and DNA N-Methyltransferase 1 (DNMT1) Genetic Polymorphism.
Infections
A coupled fluorescence-based assay for the detection of protein arginine N-methyltransferase 6 (PRMT6) enzymatic activity.
Infections
Downregulation of histone methyltransferase EHMT2 in CD4(+) T-cells may protect HTLV-1-infected individuals against HAM/TSP development.
Influenza, Human
Evidence for a novel mechanism of influenza A virus host adaptation modulated by PB2-627.
Leukemia
Proteolytically cleaved MLL subunits are susceptible to distinct degradation pathways.
Leukemia
Reprogramming Antagonizes the Oncogenicity of HOXA13-Long Noncoding RNA HOTTIP Axis in Gastric Cancer Cells.
Leukemia, Myeloid, Acute
DNMT3A mutants provide proliferating advantage with augmentation of self-renewal activity in the pathogenesis of AML in KMT2A-PTD-positive leukemic cells.
Leukemia, Myeloid, Acute
The Application of Targeted RNA Sequencing for KMT2A-Partial Tandem Duplication Identification and Integrated Analysis of Molecular Characterization in Acute Myeloid Leukemia.
Liver Diseases
Fatty liver and fibrosis in glycine N-methyltransferase knockout mice is prevented by nicotinamide.
Lordosis
Inhibition of guinea pig lordosis behavior by the phenylethanolamine N-methyltransferase (PNMT) inhibitor SKF-64139: mediation by alpha noradrenergic receptors.
Lung Injury
Endotoxin stabilizes protein arginine methyltransferase 4 (PRMT4) protein triggering death of lung epithelia.
Lung Neoplasms
Downregulation of histone-lysine N-methyltransferase EZH2 inhibits cell viability and enhances chemosensitivity in lung cancer cells.
Neoplasm Metastasis
An oncogene-tumor suppressor cascade drives metastatic prostate cancer by coordinately activating Ras and nuclear factor-kappaB.
Neoplasm Metastasis
Elevated N-methyltransferase expression induced by hepatic stellate cells contributes to the metastasis of hepatocellular carcinoma via regulation of the CD44v3 isoform.
Neoplasm Metastasis
Preprogramming therapeutic response of PI3K/mTOR dual inhibitor via the regulation of EHMT2 and p27 in pancreatic cancer.
Neoplasm Metastasis
Protein arginine N-methyltransferase 1 promotes the proliferation and metastasis of hepatocellular carcinoma cells.
Neoplasms
A coupled fluorescence-based assay for the detection of protein arginine N-methyltransferase 6 (PRMT6) enzymatic activity.
Neoplasms
Accumulation of low-dose BIX01294 promotes metastatic potential of U251 glioblastoma cells.
Neoplasms
Comprehensive Cancer Panel Sequencing Defines Genetic Diversity and Changes in the Mutational Characteristics of Pancreatic Cancer Patients Receiving Neoadjuvant Treatment.
Neoplasms
Computational discovery and biological evaluation of novel inhibitors targeting histone-lysine N-methyltransferase SET7.
Neoplasms
Coronin 2A (CRN5) expression is associated with colorectal adenoma-adenocarcinoma sequence and oncogenic signalling.
Neoplasms
DAL-1/4.1B tumor suppressor interacts with protein arginine N-methyltransferase 3 (PRMT3) and inhibits its ability to methylate substrates in vitro and in vivo.
Neoplasms
Downregulation of histone-lysine N-methyltransferase EZH2 inhibits cell viability and enhances chemosensitivity in lung cancer cells.
Neoplasms
Epigenetic priming by EHMT1/EHMT2 in acute lymphoblastic leukemia induces TP53 and TP73 overexpression and promotes cell death.
Neoplasms
Genomic alterations in KMT2 family predict outcome of immune checkpoint therapy in multiple cancers.
Neoplasms
Identification of Novel Inhibitors against Coactivator Associated Arginine Methyltransferase 1 Based on Virtual Screening and Biological Assays.
Neoplasms
Identification of protein arginine N-methyltransferase 5 (PRMT5) as a novel interacting protein with the tumor suppressor protein RASSF1A.
Neoplasms
Inactivation of the Euchromatic Histone-Lysine N-Methyltransferase 2 Pathway in Pancreatic Epithelial Cells Antagonizes Cancer Initiation and Pancreatitis-Associated Promotion by Altering Growth and Immune Gene Expression Networks.
Neoplasms
Increased expression of G9A contributes to carcinogenesis and indicates poor prognosis in hepatocellular carcinoma.
Neoplasms
Inhibition of euchromatin histone-lysine N-methyltransferase 2 sensitizes breast cancer cells to tumor necrosis factor-related apoptosis-inducing ligand through reactive oxygen species-mediated activating transcription factor 4-C/EBP homologous protein-death receptor 5 pathway activation.
Neoplasms
Integration of comprehensive genomic profiling, tumor mutational burden, and PD-L1 expression to identify novel biomarkers of immunotherapy in non-small cell lung cancer.
Neoplasms
Morphology, Biochemistry, and Pathophysiology of MENX-Related Pheochromocytoma Recapitulate the Clinical Features.
Neoplasms
Nicotinamide supplementation induces detrimental metabolic and epigenetic changes in developing rats.
Neoplasms
Protein arginine N-methyltransferase 1 promotes the proliferation and metastasis of hepatocellular carcinoma cells.
Neoplasms
Reduced expression of SETD2 and SNX9 proteins in chemically induced mammary tumorigenesis in Wistar rats: a prognostic histological and proteomic study.
Neoplasms
Reprogramming Antagonizes the Oncogenicity of HOXA13-Long Noncoding RNA HOTTIP Axis in Gastric Cancer Cells.
Neoplasms
RNAi-mediated EZH2 depletion decreases MDR1 expression and sensitizes multidrug-resistant hepatocellular carcinoma cells to chemotherapy.
Neoplasms
Structural Insights into Ternary Complex Formation of Human CARM1 with Various Substrates.
Neoplasms
The Promise for Histone Methyltransferase Inhibitors for Epigenetic Therapy in Clinical Oncology: A Narrative Review.
Neoplasms
The tumor suppressor DAL-1/4.1B modulates protein arginine N-methyltransferase 5 activity in a substrate-specific manner.
Neoplasms
Up-regulated long non-coding RNA DUXAP8 promotes cell growth through repressing Krüppel-like factor 2 expression in human hepatocellular carcinoma.
Neoplasms
Wedelolactone Targets EZH2-mediated Histone H3K27 Methylation in Mantle Cell Lymphoma.
Neuroblastoma
EHMT2 inhibitor BIX-01294 induces apoptosis through PMAIP1-USP9X-MCL1 axis in human bladder cancer cells.
Ovarian Neoplasms
Dual role of PRMT1-dependent arginine methylation in cellular responses to genotoxic stress.
Pancreatic Neoplasms
KMT2D deficiency enhances the anti-cancer activity of L48H37 in pancreatic ductal adenocarcinoma.
Pancreatic Neoplasms
Preprogramming therapeutic response of PI3K/mTOR dual inhibitor via the regulation of EHMT2 and p27 in pancreatic cancer.
Paralysis
Asymmetric dimethylarginine exacerbates A?-induced toxicity and oxidative stress in human cell and Caenorhabditis elegans models of Alzheimer disease.
Parkinson Disease
(R)salsolinol N-methyltransferase activity increases in parkinsonian lymphocytes.
Parkinson Disease
A neutral N-methyltransferase activity in the striatum determines the level of an endogenous MPP+-like neurotoxin, 1,2-dimethyl-6,7-dihydroxyisoquinolinium ion, in the substantia nigra of human brains.
Parkinson Disease
Characterization of brain beta-carboline-2-N-methyltransferase, an enzyme that may play a role in idiopathic Parkinson's disease.
Parkinson Disease
Dopamine-derived endogenous N-methyl-(R)-salsolinol: its role in Parkinson's disease.
Parkinson Disease
Dopamine-derived salsolinol derivatives as endogenous monoamine oxidase inhibitors: occurrence, metabolism and function in human brains.
Parkinson Disease
Increased beta-carboline 9N-methyltransferase activity in the frontal cortex in Parkinson's disease.
Parkinson Disease
Involvement of endogenous N-methyl(R)salsolinol in Parkinson's disease: induction of apoptosis and protection by (-)deprenyl.
Parkinson Disease
N-methyl(R)salsolinol and a neutral N-methyltransferase as pathogenic factors in Parkinson's disease.
Pneumonia
Endotoxin stabilizes protein arginine methyltransferase 4 (PRMT4) protein triggering death of lung epithelia.
Prader-Willi Syndrome
Epigenetics meets GPCR: inhibition of histone H3 methyltransferase (G9a) and histamine H3 receptor for Prader-Willi Syndrome.
Prostatic Neoplasms
EHMT2 promotes the development of prostate cancer by inhibiting PI3K/AKT/mTOR pathway.
Sarcoma
The Promise for Histone Methyltransferase Inhibitors for Epigenetic Therapy in Clinical Oncology: A Narrative Review.
Seizures
The effects of histamine H3-receptor antagonists on amygdaloid kindled seizures in rats.
Starvation
Changes in histamine metabolism in the brains of mice with streptozotocin-induced diabetes.
Stomach Neoplasms
Large-scale analysis of KMT2 mutations defines a distinctive molecular subset with treatment implication in gastric cancer.
Thymoma
Skeletal muscle-specific Prmt1 deletion causes muscle atrophy via deregulation of the PRMT6-FOXO3 axis.
Urinary Bladder Neoplasms
Analysis of the role of mutations in the KMT2D histone lysine methyltransferase in bladder cancer.
Urinary Bladder Neoplasms
EHMT2 inhibitor BIX-01294 induces apoptosis through PMAIP1-USP9X-MCL1 axis in human bladder cancer cells.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
kinetics of the ancestral enzyme, overview
-
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
in vivo activities after feeding of radiolabeled L-methionine, activity profile of the enzyme in young, adult, and aged leaves, overview
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.5
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
27
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene CaMTL3, enzyme XMT1; var. caturra, two different N-methyltransferases XMT and MXMT
SwissProt
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
immature, ripening, and mature, enzyme expression and activity during development, overview
brenda
high expression level in immature fruits, low expression in mature fruits
brenda
-
immature, ripening, and mature, enzyme expression and activity during development, overview
brenda
-
immature, ripening, and mature, enzyme expression and activity during development, overview
-
brenda
-
activity profile of the enzyme in young, adult, and aged leaves, high activity in young leaves
brenda
very high expression in young leaves, moderate expression in expanded leaves
brenda
additional information
method development for somatic embryogenesis, overview
brenda
additional information
-
method development for somatic embryogenesis, overview
brenda
additional information
-
method development for somatic embryogenesis, overview
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
co-localization of xanthosine methyltransferase, 7-methylxanthine methyltransferase, and 3,7-dimethylxanthine methyltransferase
brenda
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
metabolism
physiological function
-
the major purine alkaloids accumulated in Camellia gymnogyna are theobromine together with a small amount of theacrine and caffeine. The recombinant GCS2 is not active with any xanthine derivative tested
additional information
evolution
evolutionary relationship of caffeine synthases and its related enzymes, phylogenetic analysis and tree, overview
evolution
evolutionary relationship of caffeine synthases and its related enzymes, phylogenetic analysis and tree, overview
evolution
ancestral biosynthetic catalytic capabilities might lead to convergent evolution of similar modern-day biochemical pathways. Analysis of ancient enzymes of the caffeine synthase (CS) methyltransferases that are responsible for theobromine and caffeine production in flowering plants. Ancestral CS enzymes of Theobroma, Paullinia, and Camellia exhibited similar substrate preferences but these resulted in the formation of different sets of products, overview. From these ancestral enzymes, descendants with similar substrate preference and product formation independently evolved after gene duplication events in Theobroma and Paullinia. The convergent modern-day pathways likely originated independently via gene duplication from ancestral pathways with different inferred flux and their convergent catalytic characteristics evolved to partition the multiple ancestral activities by different mutations that occurred in homologous regions of the ancestral proteins
evolution
ancestral biosynthetic catalytic capabilities might lead to convergent evolution of similar modern-day biochemical pathways. Analysis of ancient enzymes of the caffeine synthase (CS) methyltransferases that are responsible for theobromine and caffeine production in flowering plants. Ancestral CS enzymes of Theobroma, Paullinia, and Camellia exhibited similar substrate preferences but these resulted in the formation of different sets of products, overview. From these ancestral enzymes, descendants with similar substrate preference and product formation independently evolved after gene duplication events in Theobroma and Paullinia. The convergent modern-day pathways likely originated independently via gene duplication from ancestral pathways with different inferred flux and their convergent catalytic characteristics evolved to partition the multiple ancestral activities by different mutations that occurred in homologous regions of the ancestral proteins
evolution
ancestral biosynthetic catalytic capabilities might lead to convergent evolution of similar modern-day biochemical pathways. Analysis of ancient enzymes of the caffeine synthase (CS) methyltransferases that are responsible for theobromine and caffeine production in flowering plants. Ancestral CS enzymes of Theobroma, Paullinia, and Camellia exhibited similar substrate preferences but these resulted in the formation of different sets of products, overview. From these ancestral enzymes, descendants with similar substrate preference and product formation independently evolved after gene duplication events in Theobroma and Paullinia. The convergent modern-day pathways likely originated independently via gene duplication from ancestral pathways with different inferred flux and their convergent catalytic characteristics evolved to partition the multiple ancestral activities by different mutations that occurred in homologous regions of the ancestral proteins
evolution
-
the amino acid sequence of GCS2 shared highest homology with TCS2 (98.6%), a 7-methylxanthosine synthase (XMT). Sequence alignment reveals that GCS2 contains typical motif A, motif B', motif C, and YFFF regions
metabolism
-
methylation of xanthosine by 7-methylxanthosine synthase is the most plausible rate-limiting step of caffeine biosynthesis, the supply of non-methylated purine precursors or availability of S-adenosyl-L-methionine are not the principal controlling factors of caffeine biosynthesis
metabolism
-
the enzyme catalyzes the first step in caffeine biosynthesis, pathway overview
metabolism
-
expression levels of genes GCS1, GCS2, GCS3, and TCS1 and purine alkaloid content in different leaf positions of Camellia gymnogyna, Camellia sinensis, Theobroma cocoa, and Camellia sinensis var. assamica cv. Kucha, overview
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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). XMT1_COFCA
372
0
41816
Swiss-Prot
Secretory Pathway (Reliability: 1)
XMT1_COFAR
372
0
41842
Swiss-Prot
other Location (Reliability: 3)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
dimer
-
bimolecular fluorescence complementation. Enzymes xanthosine methyltransferase, 7-methylxanthine methyltransferase, and 3,7-dimethylxanthine methyltransferase each form a homo-dimer in cytosol. In addition, each enzyme also forms a hetero-dimer with each of the other two enzymes in cytosol
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
purified recombinant wild-type and selenomethionine-labeled XMT, 23-28% PEG 3350, 0.2 M LiCl, 0.1 M Tris-HCl, pH 8.5-8.7, 2 mM DTT, 1 mM S-adenosyl-L-cysteine, and 1 mM xanthosine, 1-3 days, 20°C, X-ray diffraction structure determination and analysis at 2.8-3.0 A resolution
purified recombinant wild-type and selenomethionine-labeled XMT, 23-28% PEG 3350, 0.2 M LiCl, 0.1 M Tris-HCl, pH 8.5-8.7, 2 mM DTT, 2 mM S-adenosyl-L-cysteine, and 2 mM xanthosine, 1-3 days, 20°C, plate-like crystals, X-ray diffraction structure determination and analysis at 2.2 A resolution
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
A23S
-
site-directed mutagenesis, the mutant exhibits no 3-N methylation activity like the wild-type, the mutant shows over 80% of wild-type 7-methylation activity
A23S/L191P/H219R
-
site-directed mutagenesis, the mutant exhibits no 3-N methylation activity like the wild-type, the mutant shows over 80% of wild-type 7-methylation activity
A23S/P104Q/H219R
-
site-directed mutagenesis, the mutant exhibits no 3-N methylation activity like the wild-type, the mutant shows over 80% of wild-type 7-methylation activity
A23S/P104Q/Q161H/H219R
-
site-directed mutagenesis, the mutant exhibits 3-N methylation activity in contrast to the wild-type enzyme, the mutant shows 60% of wild-type 7-methylation activity
A23S/P104Q/Q161H/L191P/H219R
-
site-directed mutagenesis, the mutant exhibits 3-N methylation activity in contrast to the wild-type enzyme, the mutant shows over 80% of wild-type 7-methylation activity
A23S/Q161H/H219R
-
site-directed mutagenesis, the mutant exhibits 3-N methylation activity in contrast to the wild-type enzyme, the mutant shows over 80% of wild-type 7-methylation activity
A23S/Q161H/L191P/H219R
-
site-directed mutagenesis, the mutant exhibits 3-N methylation activity in contrast to the wild-type enzyme, the mutant shows over 80% of wild-type 7-methylation activity
H219R
-
site-directed mutagenesis, the mutant exhibits no 3-N methylation activity like the wild-type, the mutant shows over 80% of wild-type 7-methylation activity
L191P
-
site-directed mutagenesis, the mutant exhibits no 3-N methylation activity like the wild-type, the mutant shows over 80% of wild-type 7-methylation activity
P104Q
-
site-directed mutagenesis, the mutant exhibits no 3-N methylation activity like the wild-type, the mutant shows over 80% of wild-type 7-methylation activity
P104Q/L191P
-
site-directed mutagenesis, the mutant exhibits no 3-N methylation activity like the wild-type, the mutant shows over 80% of wild-type 7-methylation activity
P104Q/Q161H
-
site-directed mutagenesis, the mutant exhibits 3-N methylation activity in contrast to the wild-type enzyme, the mutant shows over 80% of wild-type 7-methylation activity
P104Q/Q161H/L191P
-
site-directed mutagenesis, the mutant exhibits 3-N methylation activity in contrast to the wild-type enzyme, the mutant shows over 80% of wild-type 7-methylation activity
Q161H
-
site-directed mutagenesis, the mutant exhibits 3-N methylation activity in contrast to the wild-type enzyme, the mutant shows over 80% of wild-type 7-methylation activity
Q161H/L191P
-
site-directed mutagenesis, the mutant exhibits 3-N methylation activity in contrast to the wild-type enzyme, the mutant shows over 80% of wild-type 7-methylation activity
additional information
additional information
reduction of the second enzyme of the pathway, 7-methylxanthine methyltransferase, EC 2.1.1.159, leads to reduced XMT1 expression
additional information
-
reduction of the second enzyme of the pathway, 7-methylxanthine methyltransferase, EC 2.1.1.159, leads to reduced XMT1 expression
additional information
transgenic Nicotiana tabacum plant leaves expressing all three enzymes required for the biosynthesis of caffeine are no longer eaten by the tobacco cutworm caterpillars, Spodoptera litura, overview
additional information
-
reduction of the second enzyme of the pathway, 7-methylxanthine methyltransferase, EC 2.1.1.159, leads to reduced XMT1 expression
additional information
-
construction of several enzyme mutants, overview. The mutants of CmXRS1, that have 3-N methylation activity and produce caffeine from paraxanthine as a substrate, need to have replacement of the glutamine residue by histidine at position 161 in the CmXRS1 sequence, i.e. a Q161H mutation, overview
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
native enzyme 9fold from young leaves by 3 steps of ion exchange chromatography, and gel filtration
-
native enzyme partially from young leaves by ammonium sulfate fractionation, gel filtration, and ultrafiltration
-
recombinant His-tagged XMT1 from Escherichia coli strain BL21(DE3) to homogeneity by nickel affinity chromatography, cleavage of the His-tag with tobacco etch virus, TEV, protease, followed by gel filtration
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression of wild-type and mutant enzymes in Escherichia coli strain BL21 (DE3), sequence comparison of caffeine synthetic enzymes from coffee
-
gene CaMTL3, cDNA library construction, DNA and amino acid sequence determination and analysis, sequence comparison with other species
gene CtCS1 or CaXMT1 or CmXRS1, DNA sequence determination, phylogenetic tree, expression in Escherichia coli strain BL21(DE3)
gene GCS2, DNA and amino acid sequence determination and analysis, cloning sequence comparisons and phylogenetic analysis, quantitative RT-PCR enzyme expression analysis and tree, recombinant expression in Escherichia coli
-
gene XMT1, DNA and amino acid sequence determination and analysis, expression analysis
gene XMT1, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis
isozyme XMT1, DNA and amino acid sequence determination and analysis, phylogenetic analysis, expression of the GST-tagged enzyme in Escherichia coli Bl21(DE3)
isozyme XMT1, functional expression in transgenic Nicotiana tabacum plant leaves
gene XMT1, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis
gene XMT1, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expression is increased in presence of methyl jasmonate. 0.5 mM salicylic acid upregulates expression, but 0.05 mM does not
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
expression of the caffeine biosynthesis enzymes in transgenic crop plants amay protect against the crop damaging larvae of pests
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Koshiishi, C.; Kato, A.; Yama, S.; Crozier, A.; Ashihara, H.
A new caffeine biosynthetic pathway in tea leaves: utilisation of adenosine released from the S-adenosyl-L-methionine cycle
FEBS Lett.
499
50-54
2001
Camellia sinensis
brenda
McCarthy, A.A.; Biget, L.; Lin, C.; Petiard, V.; Tanksley, S.D.; McCarthy, J.G.
Cloning, expression, crystallization and preliminary x-ray analysis of the XMT and DXMT N-methyltransferases from Coffea canephora (robusta)
Acta Crystallogr. Sect. F
F63
304-307
2007
Coffea canephora (A4GE69)
brenda
Moisyadi, S.; Neupane, K.R.; Stiles, J.I.
Cloning and characterization of a cDNA encoding xanthosine-N7-methyltransferase from coffee (Coffea arabica)
Acta Hortic.
461
367-377
1998
Coffea arabica
-
brenda
Negishi, O.; Ozawa, T.; Imagawa, H.
The role of xanthosine in the biosynthesis of caffeine in coffe plants
Agric. Biol. Chem.
49
2221-2222
1985
Coffea arabica
-
brenda
Mizuno, K.; Kato, M.; Irino, F.; Yoneyama, N.; Fujimura, T.; Ashihara, H.
The first committed step reaction of caffeine biosynthesis: 7-methylxanthosine synthase is closely homologous to caffeine synthases in coffee (Coffea arabica L.)
FEBS Lett.
547
56-60
2003
Coffea arabica (Q9AVK0)
brenda
Ogawa, M.; Herai, Y.; Koizumi, N.; Kusano, T.; Sano, H.
7-Methylxanthine methyltransferase of coffee plants. Gene isolation and enzymatic properties
J. Biol. Chem.
276
8213-8218
2001
Coffea arabica (Q9AVK0)
brenda
Waldhauser, S.S.M.; Gillies, F.M.; Crozier, A.; Baumann, T.W.
Separation of the N-7 methyltransferase, the key enzyme in caffeine biosynthesis
Phytochemistry
45
1407-1414
1997
Coffea arabica
brenda
Ogita, S.; Uefuji, H.; Morimoto, M.; Sano, H.
Application of RNAi to confirm theobromine as the major intermediate for caffeine biosynthesis in coffee plants with potential for construction of decaffeinated varieties
Plant Mol. Biol.
54
931-941
2004
Coffea arabica (Q9AVK0), Coffea arabica, Coffea canephora
brenda
Uefuji, H.; Tatsumi, Y.; Morimoto, M.; Kaothien-Nakayama, P.; Ogita, S.; Sano, H.
Caffeine production in tobacco plants by simultaneous expression of three coffee N-methyltranferases and its potential as a pest repellant
Plant Mol. Biol.
59
221-227
2005
Coffea arabica (Q9AVK0)
brenda
Uefuji, H.; Ogita, S.; Yamaguchi, Y.; Koizumi, N.; Sano, H.
Molecular cloning and functional characterization of three distinct N-methyltransferases involved in the caffeine biosynthetic pathway in coffee plants
Plant Physiol.
132
372-380
2003
Coffea arabica (Q9AVK0)
brenda
McCarthy, A.A.; McCarthy, J.G.
The structure of two N-methyltransferases from the caffeine biosynthetic pathway
Plant Physiol.
144
879-889
2007
Coffea canephora (A4GE69)
brenda
Koshiro, Y.; Zheng, X.Q.; Wang, M.L.; Nagai, C.; Ashihara, H.
Changes in content and biosynthetic activity of caffeine and rigonelline during growth and ripening of Coffea arabica and Coffea canephora fruits
Plant Sci.
171
242-250
2006
Coffea arabica (Q9AVK0), Coffea canephora
-
brenda
Kodama, Y.; Shinya, T.; Sano, H.
Dimerization of N-methyltransferases involved in caffeine biosynthesis
Biochimie
90
547-551
2008
Coffea arabica
brenda
Deng, W.; Li, Y.; Ogita, S.; Ashihara, H.
Fine control of caffeine biosynthesis in tissue cultures of Camellia sinensis
Phytochem. Lett.
1
195-198
2008
Camellia sinensis
-
brenda
Mizuno, K.; Kurosawa, S.; Yoshizawa, Y.; Kato, M.
Essential region for 3-N methylation in N-methyltransferases involved in caffeine biosynthesis
Z. Naturforsch. C
65c
257-265
2010
Coffea sp.
brenda
Qian, P.; Guo, H.B.; Yue, Y.; Wang, L.; Yang, X.; Guo, H.
Understanding the catalytic mechanism of xanthosine methyltransferase in caffeine biosynthesis from QM/MM molecular dynamics and free energy simulations
J. Chem. Inf. Model.
56
1755-1761
2016
Coffea canephora (A4GE69)
brenda
Kumar, A.; Giridhar, P.
Salicylic acid and methyljasmonate restore the transcription of caffeine biosynthetic N-methyltransferases from a transcription inhibition noticed during late endosperm maturation in coffee
Plant Gene
4
38-44
2015
Coffea canephora (A4GE69)
-
brenda
Zhou, M.Z.; Yan, C.Y.; Zeng, Z.; Luo, L.; Zeng, W.; Huang, Y.H.
N-Methyltransferases of caffeine biosynthetic pathway in plants
J. Agric. Food Chem.
68
15359-15372
2020
Coffea arabica (Q9AVK0), Coffea arabica (A0A096VHY7), Coffea canephora (A4GE69)
brenda
O'Donnell, A.J.; Huang, R.; Barboline, J.J.; Barkman, T.J.
Convergent biochemical pathways for xanthine alkaloid production in plants evolved from ancestral enzymes with different catalytic properties
Mol. Biol. Evol.
38
2704-2714
2021
Coffea canephora (A4GE69), Camellia sinensis (Q68CM3), Coffea arabica (Q9AVK0)
brenda
Zhou, M.Z.; ONeill Rothenberg, D.; Zeng, W.; Luo, L.; Yan, C.Y.; Zeng, Z.; Huang, Y.H.
Discovery and biochemical characterization of N-methyltransferase genes involved in purine alkaloid biosynthetic pathway of Camellia gymnogyna Hung T.Chang (Theaceae) from Dayao mountain
Phytochemistry
199
113167
2022
Camellia gymnogyna
brenda
EXTERNAL LINKS (specific for EC-Number 2.1.1.158)
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