Information on EC 2.1.1.157 - sarcosine/dimethylglycine N-methyltransferase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea

EC NUMBER
COMMENTARY hide
2.1.1.157
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RECOMMENDED NAME
GeneOntology No.
sarcosine/dimethylglycine N-methyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
2 S-adenosyl-L-methionine + sarcosine = 2 S-adenosyl-L-homocysteine + betaine
show the reaction diagram
S-adenosyl-L-methionine + N,N-dimethylglycine = S-adenosyl-L-homocysteine + betaine
show the reaction diagram
S-adenosyl-L-methionine + sarcosine = S-adenosyl-L-homocysteine + N,N-dimethylglycine
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Glycine, serine and threonine metabolism
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glycine betaine biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:sarcosine(or N,N-dimethylglycine) N-methyltransferase [N,N-dimethylglycine(or betaine)-forming]
Cells of the oxygen-evolving halotolerant cyanobacterium Aphanocthece halophytica synthesize betaine from glycine by a three-step methylation process. The first enzyme, EC 2.1.1.156, glycine/sarcosine N-methyltransferase, leads to the formation of either sarcosine or N,N-dimethylglycine, which is further methylated to yield betaine (N,N,N-trimethylglycine) by the action of this enzyme. Both of these enzymes can catalyse the formation of N,N-dimethylglycine from sarcosine [3]. The reactions are strongly inhibited by S-adenosyl-L-homocysteine.
CAS REGISTRY NUMBER
COMMENTARY hide
294211-00-0
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
ATCC 27976
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Manually annotated by BRENDA team
gene smdA encodes a Sdm homologue protein
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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disruption of the sdmA gene, encoding Sdm homologue protein, generates a mutant that exhibits a longer lag period of growth and delayed spore germination under osmostress, it shows normal growth in CYE medium at 30C, phenotype, overview
metabolism
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glycine sarcosine methyltransferase, EC 2.1.1.156, and sarcosine dimethylglycine methyltransferase catalyze glycine betaine synthesis from glycine
physiological function
additional information
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 + glycine
S-adenosyl-L-homocysteine + sarcosine
show the reaction diagram
low activity
-
-
?
S-adenosyl-L-methionine + N,N-dimethylglycine
S-adenosyl-L-homocysteine + betaine
show the reaction diagram
S-adenosyl-L-methionine + N,N-dimethylglycine
S-adenosyl-L-homocysteine + betaine + H+
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + N,N-dimethylglycine
S-adenosyl-L-homocysteine + N,N,N-trimethylglycine
show the reaction diagram
S-adenosyl-L-methionine + N-methylglycine
S-adenosyl-L-homocysteine + N,N-dimethylglycine
show the reaction diagram
S-adenosyl-L-methionine + sarcosine
S-adenosyl-L-homocysteine + betaine
show the reaction diagram
(overall reaction)
-
-
?
S-adenosyl-L-methionine + sarcosine
S-adenosyl-L-homocysteine + N,N-dimethylglycine
show the reaction diagram
S-adenosyl-L-methionine + sarcosine
S-adenosyl-L-homocysteine + N,N-dimethylglycine + H+
show the reaction diagram
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about 30% of the activity with N,N-dimethylglycine
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-
?
additional information
?
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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 + N,N-dimethylglycine
S-adenosyl-L-homocysteine + betaine
show the reaction diagram
S-adenosyl-L-methionine + N,N-dimethylglycine
S-adenosyl-L-homocysteine + N,N,N-trimethylglycine
show the reaction diagram
S-adenosyl-L-methionine + N-methylglycine
S-adenosyl-L-homocysteine + N,N-dimethylglycine
show the reaction diagram
S-adenosyl-L-methionine + sarcosine
S-adenosyl-L-homocysteine + N,N-dimethylglycine
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
S-adenosyl-L-methionine
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
K+
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highest activity at 0.8 M K+
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4-chloromercuribenzoate
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recombinant enzyme: 23% inhibition at 1.33 mM, completely reversible by 5.3 mM DTT
betaine
dimethylglycine
competitive inhibition, versus sarcosine, 40% inhibition at 250 mM
isovaleric acid
10% inhibition at 250 mM, with dimethylglycine
KCl/NaCl
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recombinant enzyme: 32% inhibition at 0.33 M KCl and 0.66 M NaCl with sarcosine, and 25% inhibition at 0.33 M KCl and 0.66 M NaCl with dimethylglycine, decrease inhibition by betaine, overview
L-alanine
10% inhibition at 250 mM, with dimethylglycine
L-cysteine
10% inhibition at 250 mM, with dimethylglycine
L-methionine
10% inhibition at 250 mM, with dimethylglycine
L-phenylalanine
10% inhibition at 250 mM
n-butyric acid
50% inhibition at 250 mM, with dimethylglycine
propionic acid
10% inhibition at 250 mM, with dimethylglycine
S-adenosyl-L-homocysteine
sarcosine
slight competitive inhibition, versus dimethylglycine, 20% inhibition at 250 mM
tert-butylacetic acid
30% inhibition at 250 mM, with dimethylglycine
additional information
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
abiotic stess-inducible enzyme, e.g. high salt content
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.5 - 7.5
dimethylglycine
2.8 - 3.76
N,N-dimethylglycine
0.144 - 0.79
S-adenosyl-L-methionine
0.8 - 6.1
sarcosine
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.4 - 2.68
N,N-dimethylglycine
0.44 - 1.07
sarcosine
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.15 - 0.4
S-adenosyl-L-homocysteine
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.23
activity with sarcosine and S-adenosyl-L-methionine in crude cell extracts
0.34
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activity with sarcosine and S-adenosyl-L-methionine in crude cell extracts
0.36
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activity with sarcosine and S-adenosyl-L-methionine, purified enzyme
0.68
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purified recombinant enzyme, substrate sarcosine
0.71
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pH 7.2, 37C, sarcosine N-methyltransferase activity
0.93
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activity with N,N-dimethylglycine and S-adenosyl-L-methionine in crude cell extracts
1
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activity with N,N-dimethylglycine and S-adenosyl-L-methionine, purified enzyme
2.6
activity with N,N-dimethylglycine and S-adenosyl-L-methionine in crude cell extracts
3
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pH 7.2, 37C, N,N-dimethylglycine N-methyltransferase activity
3.4
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purified recombinant enzyme, substrate dimethylglycine
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.6
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recombinant enzyme, with substrate dimethylglycine, triethanolamine buffer
8
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methylation of sarcosine
8 - 9
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recombinant enzyme, with substrate sarcosine, pH-optimum depends on the buffer system
additional information
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pH-optimum depends on the buffer system
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5
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isoelectric focusing
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25000
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gel filtration
27900
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x * 27900, about, sequence calculation
29000
recombinant enzyme, gel filtration
30690
2 * 30690, sequence calculation, 2 * 38000, SDS-PAGE
31000
1 * 31000, recombinant enzyme, SDS-PAGE
33000
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gel fitlration
34000
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2 * 34000, denaturing PAGE
36000
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1 * 36000, recombinant enzyme, SDS-PAGE, 1 * 32000, about, amino acid sequence calculation
38000
2 * 30690, sequence calculation, 2 * 38000, SDS-PAGE
67700
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 27900, about, sequence calculation
monomer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor-diffusion method, crystal structure of the enzyme, solved to a resolution of 1.95 A
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formation of monoclinic crystals, diffracting to 2.15 A resolution, and orthorhombic crystals, diffracting to 1.8 A resolution
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
61
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melting temperature
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-85C, 5 months, no significant loss of both activities
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
by AMP affinity chromatography and ultrafiltration
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recombinant enzyme from Escherichia coli by ammonium sulfate fractionation and ion exchange chromatography to homogeneity
recombinant enzyme from Escherichia coli by ammonium sulfate fractionation, hydrophobic and anion exchange chromatography, and ultrafiltration to homogeneity
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recombinant MpSDMT from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination, the single gene encodes the sarcosine dimethylglycine methyltransferase as well as the glycine sarcosine methyltransferase, EC 2.1.1.156, the first being probably a proteolytic processing product of the latter, functional expression of a truncated soluble enzyme form in Escherichia coli
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expressed in Anabaena doliolum
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expressed in Oryza sativa cultivar Nipponbare
expressed in Zea mays
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expression in Escherichia coli
functional overexpression in Escherichia coli strain XL-1 Blue conferring betaine accumulation and increased salt tolerance when coexpressed with the glycine sarcosine methyltransferase, EC 2.1.1.156
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gene Mpsdmt, DNA and amino acid sequence determination and analysis and sequence comparisons, phylogenetic analysis of SDMT, expression of complete gene cluster of Mpgsmt-sdmt in Escherichia coli strain BL21(DE3) and in strain MKH13 deficient in betaine transport, the recombinant enzyme is functional to synthesize and accumulate betaine and confers elevated survival ability in betaine transport deficient mutant strain MKH13 under high salt stress
gene sdmA, DNA and amino acid sequence determination and analysis, sequence comparison
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orf2, DNA and amino acid sequence determination and analysis, phylogenetic analysis, overexpression of wild-type and mutant enzymes in Escherichia coli, functional coexpression of the soluble enzyme with the glycine sarcosine methyltransferase, EC 2.1.1.156, increases the intracellular betaine level and the growth rate of Escherichia coli strain BL21(DE3)
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
betaine downregulates GSMT expression enhanced with increasing temperature, transcription unit and transcription level of Mpgsmt-sdmt is reduced under temperature stresses up to 37C, but recovers at 45C to the level at 20C
the enzyme shows increased expression levels under drought conditions
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
M172R
site-directed mutagenesis, reduced activity with sarcosine, but highly reduced activity with dimethylglycine compared to the wild-type enzyme
P171Q
site-directed mutagenesis, reduced activity with sarcosine and dimethylglycine compared to the wild-type enzyme
P171Q/M172R
site-directed mutagenesis, reduced activity with glycine and sarcosine, but highly reduced activity with dimethylglycine compared to the wild-type enzyme
additional information
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construction of a chromosomal sdmA gene disruption knockout mutant, phenotype, overview
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
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enzyme can be used in betaine production for improvement of stress tolerance of commercially important microbes in agriculture and industry, and for nutritial improvement of transgenic crop plants, that do not produce betaine naturally
biotechnology
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enzyme can be used in betaine production for improvement of stress tolerance of commercially important microbes in agriculture and industry, and for nutritial improvement of transgenic crop plants, that do not produce betaine naturally
nutrition
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enzyme can be used in betaine production for improvement of stress tolerance of commercially important microbes in agriculture and industry, and for nutritial improvement of transgenic crop plants, that do not produce betaine naturally