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EC Tree
IUBMB Comments Paraxanthine is the best substrate for this enzyme but the paraxanthine pathway is considered to be a minor pathway for caffeine biosynthesis [2,3].
The taxonomic range for the selected organisms is: Coffea arabica The enzyme appears in selected viruses and cellular organisms
Synonyms
caffeine synthase, tea caffeine synthase, tea caffeine synthase 1, 1-n-methyltransferase, n-1 methyltransferase, 7-n-methylxanthine methyltransferase,
more
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3,7-dimethylxanthine methyltransferase
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coffee caffeine synthase 1
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N-1 methyltransferase
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S-adenosyl-L-methionine:3,7-dimethylxanthine N1-methyltransferase
Paraxanthine is the best substrate for this enzyme but the paraxanthine pathway is considered to be a minor pathway for caffeine biosynthesis [2,3].
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S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
S-adenosyl-L-methionine + 1,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
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-
-
?
S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
S-adenosyl-L-methionine + 7-methylxanthine
S-adenosyl-L-homocysteine + 3,7-dimethylxanthine
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i.e. theobromine
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?
additional information
?
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S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
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i.e. caffeine
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ir
S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
last step in caffeine biosynthesis pathway
i.e. caffeine
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ir
S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
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-
i.e. caffeine
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?
S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
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i.e. caffeine
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?
S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
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-
i.e. caffeine
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?
S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
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i.e. caffeine
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ir
S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
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last step in caffeine biosynthesis pathway
i.e. caffeine
-
?
S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
last step in caffeine biosynthesis pathway
i.e. caffeine
-
?
S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
last step in caffeine biosynthesis pathway
i.e. caffeine
-
ir
S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
step of the caffeine biosynthesis, caffeine accumulation in seeds
i.e. caffeine
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?
additional information
?
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bifunctional enzyme performing 3-N-methyltransferase activity, EC 2.1.1.159, and 1-N-methyltransferase activity, EC 2.1.1.160, overview
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-
?
additional information
?
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enzyme expression and activity during caffeine biosynthesis in fruits, overview
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-
?
additional information
?
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feeding experiments with fruit samples, determination of reaction products, overview
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?
additional information
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substrate specificity, bifunctional enzyme performing 3-N-methyltransferase activity, EC 2.1.1.159, and 1-N-methyltransferase activity, EC 2.1.1.160, overview
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-
?
additional information
?
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substrate specificity, overview, no activity with xanthine, hypoxanthine, and xanthosine
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-
?
additional information
?
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the multifunctional isozyme DXMT1 catalyzes also the reaction theobromine synthase, EC 2.1.1.159, but at lower activity compared to its N1-methyltransferase, i.e. caffeine synthase activity
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-
?
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S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
last step in caffeine biosynthesis pathway
i.e. caffeine
-
ir
S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
additional information
?
-
S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
-
i.e. caffeine
-
?
S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
-
i.e. caffeine
-
ir
S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
-
last step in caffeine biosynthesis pathway
i.e. caffeine
-
?
S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
last step in caffeine biosynthesis pathway
i.e. caffeine
-
?
S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
last step in caffeine biosynthesis pathway
i.e. caffeine
-
ir
S-adenosyl-L-methionine + 3,7-dimethylxanthine
S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine
step of the caffeine biosynthesis, caffeine accumulation in seeds
i.e. caffeine
-
?
additional information
?
-
bifunctional enzyme performing 3-N-methyltransferase activity, EC 2.1.1.159, and 1-N-methyltransferase activity, EC 2.1.1.160, overview
-
-
?
additional information
?
-
enzyme expression and activity during caffeine biosynthesis in fruits, overview
-
-
?
additional information
?
-
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feeding experiments with fruit samples, determination of reaction products, overview
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-
?
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KCN
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74% inhibition at 100 mM, but 33% activation at 10 mM
Mg2+
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4-chloromercuribenzoate
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complete inhibition at 0.5 mM, 23% inhibition at 0.05 mM
azouracil
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18% inhibition at 0.1 mM, no inhibition at 1 mM
iodoacetate
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complete inhibition at 100 mM, 89% inhibition at 10 mM
KCN
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74% inhibition at 100 mM, but 33% activation at 10 mM
N-Methylmaleimide
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complete inhibition at 1 mM, no inhibition at 0.1 mM
NaN3
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22% inhibition at 10 mM, 16% at 1 mM
additional information
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no inhibition by EDTA at 0.5-5 mM
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paraxanthine
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i.e. 1,7-dimethylxanthine, slight stimulation
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0.973
paraxanthine
recombinant DXMT1
0.01 - 0.153
S-adenosyl-L-methionine
0.01
S-adenosyl-L-methionine
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pH 8.5, 30°C
0.153
S-adenosyl-L-methionine
recombinant DXMT1
0.157
Theobromine
pH 8.5, 37°C, recombinant CCS1
0.2
Theobromine
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pH 8.5, 30°C
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additional information
recombinant enzyme
additional information
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substrate specificity, overview
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8
assay at
8.5
assay at
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additional information
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pH profile
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30
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assay at
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4 - 4.9
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chromatofocusing
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gene CaMTL1; var. caturra
SwissProt
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old and young
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developing
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brenda
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brenda
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derived from somatic embryogenesis
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low expression level
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immature
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immature, ripening, and mature, enzyme expression and activity during development, overview
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unripe, green
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young
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young
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young
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additional information
wide tissue distribution
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additional information
method development for somatic embryogenesis, overview
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co-localization of xanthosine methyltransferase, 7-methylxanthine methyltransferase, and 3,7-dimethylxanthine methyltransferase
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MXMT1_COFAR
378
0
42747
Swiss-Prot
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40000
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2 * 40000, SDS-PAGE
43300
2 * 43300, recombinant isozyme DXMT1, SDS-PAGE
67000
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about, gel filtration
81000
recombinant isozyme DXMT1, gel filtration
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dimer
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2 * 40000, SDS-PAGE
dimer
2 * 43300, recombinant isozyme DXMT1, SDS-PAGE
dimer
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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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additional information
reduction of the second enzyme of the pathway, 7-methylxanthine methyltransferase, EC 2.1.1.159, leads to reduced DXMT1 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
naturally occuring low-caffeine fruits contain an extra transcript of the caffeine synthase gene containing only part of exon 1 and all of exon 3. The sequence of the mutant caffeine synthase gene shows a substitution I266V in the enzyme active site that probably interferes with enzymatic activity. The absence of caffeine in these mutants probably results from a combination of transcriptional regulation and the presence of mutations
additional information
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naturally occuring low-caffeine fruits contain an extra transcript of the caffeine synthase gene containing only part of exon 1 and all of exon 3. The sequence of the mutant caffeine synthase gene shows a substitution I266V in the enzyme active site that probably interferes with enzymatic activity. The absence of caffeine in these mutants probably results from a combination of transcriptional regulation and the presence of mutations
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native enzyme 24fold from young leaves by 3 steps of ion exchange chromatography, and gel filtration
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gene CaMTL1, cDNA library construction, DNA and amino acid sequence determination and analysis, sequence comparison with other species
DNA and amino acid sequence determination and analysis, expression in Escherichia coli as wild-type and as Trx-fusion protein
gene DXMT1, DNA and amino acid sequence determination and analysis, expression analysis
isozyme DXMT1, DNA and amino acid sequence determination and analysis, phylogenetic analysis, expression of the GST-tagged enzyme in Escherichia coli Bl21(DE3)
isozyme DXMT1, functional expression in transgenic Nicotiana tabacum plant leaves
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naturally occuring low-caffeine fruits have a lower expression of the theobromine synthase and caffeine synthase genes and also contain an extra transcript of the caffeine synthase gene encoding a mutant form. The absence of caffeine in these mutants probably results from a combination of transcriptional regulation and the presence of mutations
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agriculture
expression of the caffeine biosynthesis enzymes in transgenic crop plants may protect against the crop damaging larvae of pests
analysis
protocol for the quantification of caffeine and for measuring the transcript levels of the gene (CCS1) encoding caffeine synthase in cell suspensions of Coffea arabica L. as well as its activity
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Mizuno, K.; Okuda, A.; Kato, M.; Yoneyama, N.; Tanaka, H.; Ashihara, H.; Fujimura, T.
Isolation of a new dual-functional caffeine synthase gene encoding an enzyme for the conversion of 7-methylxanthine to caffeine from coffee (Coffea arabica L.)
FEBS Lett.
534
75-81
2003
Coffea arabica (Q8H0D3)
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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 (Q9AVJ9)
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Roberts, M.F.; Waller, G.R.
N-methyltransferases and 7-methyl-N9-nucleoside hydrolase activity in Coffea arabica and the biosynthesis of caffeine
Phytochemistry
18
451-455
1979
Coffea arabica
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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
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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 (Q8H0D2), Coffea canephora
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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 (Q8H0D2)
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 (Q8H0D2)
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Koshiro, Y.; Zheng, X.Q.; Wang, M.L.; Nagai, C.; Ashihara, H.
Changes in content and biosynthetic activity of caffeine and trigonelline during growth and ripening of Coffea arabica and Coffea canephora fruits
Plant Sci.
171
242-250
2006
Coffea arabica (Q8H0D3), Coffea canephora, Coffea canephora CCS1
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Kodama, Y.; Shinya, T.; Sano, H.
Dimerization of N-methyltransferases involved in caffeine biosynthesis
Biochimie
90
547-551
2008
Coffea arabica
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Maluf, M.; Da Silva, C.; De Oliveira, M.; Tavares, A.; Silvarolla, M.; Guerreiro Filho, O.
Altered expression of the caffeine synthase gene in a naturally caffeine-free mutant of Coffea arabica
Genet. Mol. Biol.
32
802-810
2009
Coffea arabica (Q8H0D3), Coffea arabica
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Mizuno, K.; Matsuzaki, M.; Kanazawa, S.; Tokiwano, T.; Yoshizawa, Y.; Kato, M.
Conversion of nicotinic acid to trigonelline is catalyzed by N-methyltransferase belonged to motif B methyltransferase family in Coffea arabica
Biochem. Biophys. Res. Commun.
452
1060-1066
2014
Coffea arabica (Q8H0D3), Coffea arabica
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Pech-Ku, R.; Munoz-Sanchez, J.A.; Monforte-Gonzalez, M.; Vazquez-Flota, F.; Rodas-Junco, B.A.; Hernandez-Sotomayor, S.M.T.
Caffeine extraction, enzymatic activity and gene expression of caffeine synthase from plant cell suspensions
J. Vis. Exp.
140
e58166
2018
Coffea arabica (Q8H0D3)
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