2.1.1.281: phenylpyruvate C3-methyltransferase
This is an abbreviated version!
For detailed information about phenylpyruvate C3-methyltransferase, go to the full flat file.
Reaction
Synonyms
C-MT, ELQ87_35210, MppJ, MT SgvM, phenylpyruvate Cbeta-methyltransferase, phenylpyruvate methyltransferase, S-adenosylmethionine-dependent methyltransferase, SgvM
ECTree
2.1.1.281 phenylpyruvate C3-methyltransferaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 2.1.1.281 - phenylpyruvate C3-methyltransferase
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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-ethionine + 2-oxobutyrate
S-adenosyl-L-homocysteine + (3S)-methyl-2-oxovalerate
-
-
-
?
S-adenosyl-L-methionine + 2-oxo-3-phenylpropanoate
S-adenosyl-L-homocysteine + (3S)-2-oxo-3-methyl-3-phenylpropanoate
S-adenosyl-L-methionine + 2-oxobutyrate
S-adenosyl-L-homocysteine + 3-methyl-2-oxobutyrate
-
-
-
?
S-adenosyl-L-methionine + 2-oxovalerate
S-adenosyl-L-homocysteine + (3R)-methyl-2-oxovalerate
-
-
-
?
S-adenosyl-L-methionine + 3-phenylpyruvate
S-adenosyl-L-homocysteine + (3R)-2-oxo-3-phenylbutanoate
S-adenosyl-L-methionine + 3-phenylpyruvate
S-adenosyl-L-homocysteine + (3S)-2-oxo-3-phenylbutanoate
-
-
-
?
S-adenosyl-L-methionine + 4-methyl-2-oxovalerate
S-adenosyl-L-homocysteine + 3,4-dimethyl-2-oxovalerate
-
-
-
?
S-adenosyl-L-methionine + 4-methyl-2-oxovalerate
S-adenosyl-L-homocysteine + ?
-
-
-
?
S-adenosyl-L-methionine + pyruvate
S-adenosyl-L-homocysteine + 2-oxobutyrate
SgvM-catalyzed 13C-dimethylation of pyruvate in two steps results in formation of 3-methyl-2-oxobutyrate
-
-
?
S-adenosyl-L-methionine + 2-oxo-3-phenylpropanoate
S-adenosyl-L-homocysteine + (3S)-2-oxo-3-methyl-3-phenylpropanoate
-
the enzyme is involved in synthesis of the nonproteinogenic amino acid (2S,3S)-beta-methyl-phenylalanine, a building block of the glycopeptide antibiotic mannopeptimycin
-
-
?
S-adenosyl-L-methionine + 2-oxo-3-phenylpropanoate
S-adenosyl-L-homocysteine + (3S)-2-oxo-3-methyl-3-phenylpropanoate
-
2-oxo-3-phenylpropanoate i.e. 3-phenylpyruvate. S-Adenosyl-L-methionine has higher binding affinity for the enzyme than 2-oxo-3-phenylpropanoate, and the C-C bond formation in (3S)-2-oxo-3-methyl-3-phenylpropanoate might be the rate-limiting step, as opposed to the C-S bond breakage in S-adenosyl-L-methionine. No enzyme activity on glutamic acid, cinnamic acid, phenyl acetic acid and benzoyl acetic acid. The alpha-keto and beta-phenyl functional groups are crucial in MppJ molecular recognition. The enzyme strictly transfers a methyl group from S-adenosyl-L-methionine the beta position of 2-oxo-3-phenylpropanoate
(3S)-2-oxo-3-methyl-3-phenylpropanoate i.e. (3S)-beta-methyl-phenylpyruvate
-
?
S-adenosyl-L-methionine + 2-oxo-3-phenylpropanoate
S-adenosyl-L-homocysteine + (3S)-2-oxo-3-methyl-3-phenylpropanoate
-
the enzyme is involved in synthesis of the nonproteinogenic amino acid (2S,3S)-beta-methyl-phenylalanine, a building block of the glycopeptide antibiotic mannopeptimycin
-
-
?
S-adenosyl-L-methionine + 2-oxo-3-phenylpropanoate
S-adenosyl-L-homocysteine + (3S)-2-oxo-3-methyl-3-phenylpropanoate
-
2-oxo-3-phenylpropanoate i.e. 3-phenylpyruvate. S-Adenosyl-L-methionine has higher binding affinity for the enzyme than 2-oxo-3-phenylpropanoate, and the C-C bond formation in (3S)-2-oxo-3-methyl-3-phenylpropanoate might be the rate-limiting step, as opposed to the C-S bond breakage in S-adenosyl-L-methionine. No enzyme activity on glutamic acid, cinnamic acid, phenyl acetic acid and benzoyl acetic acid. The alpha-keto and beta-phenyl functional groups are crucial in MppJ molecular recognition. The enzyme strictly transfers a methyl group from S-adenosyl-L-methionine the beta position of 2-oxo-3-phenylpropanoate
(3S)-2-oxo-3-methyl-3-phenylpropanoate i.e. (3S)-beta-methyl-phenylpyruvate
-
?
S-adenosyl-L-methionine + 3-phenylpyruvate
S-adenosyl-L-homocysteine + (3R)-2-oxo-3-phenylbutanoate
phenylpyruvate binding structure analysis
-
-
?
S-adenosyl-L-methionine + 3-phenylpyruvate
S-adenosyl-L-homocysteine + (3R)-2-oxo-3-phenylbutanoate
Arg127 is electrostatically associated with phenylpyruvate, binding structure analysis, enzyme MppJ is an R-configuration-specific methyltransferase, ratios of 5:1 and 1:1 for (2S,3R)-betaMePhe versus (2S,3S)-betaMePhe
-
-
?
S-adenosyl-L-methionine + 3-phenylpyruvate
S-adenosyl-L-homocysteine + (3R)-2-oxo-3-phenylbutanoate
phenylpyruvate binding structure analysis
-
-
?
S-adenosyl-L-methionine + 3-phenylpyruvate
S-adenosyl-L-homocysteine + (3R)-2-oxo-3-phenylbutanoate
Arg127 is electrostatically associated with phenylpyruvate, binding structure analysis, enzyme MppJ is an R-configuration-specific methyltransferase, ratios of 5:1 and 1:1 for (2S,3R)-betaMePhe versus (2S,3S)-betaMePhe
-
-
?
additional information
?
-
aside from its physiological substrate 4-methyl-2-oxovalerate, enzyme SgvM catalyzes the (di)methylation of pyruvate, 2-oxobutyrate, 2-oxovalerate, and phenylpyruvate at the beta-carbon atom. SgvM acts stereoselectively. SgvM also catalyzes stereoselective ethylation reactions with S-adenosylethionine as the electrophile. The methylation of 2-oxovalerate occurs with R selectivity while the ethylation of 2-oxobutyrate with S-adenosylethionine results in the S enantiomer of 3-methyl-2-oxovalerate. Product analysis by 13C NMR spectroscopy
-
-
-
additional information
?
-
the enzyme has no nonheme oxygenase activity
-
-
?
additional information
?
-
the enzyme has no nonheme oxygenase activity
-
-
?
