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Literature summary for 2.1.1.281 extracted from

  • Huang, Y.T.; Lyu, S.Y.; Chuang, P.H.; Hsu, N.S.; Li, Y.S.; Chan, H.C.; Huang, C.J.; Liu, Y.C.; Wu, C.J.; Yang, W.B.; Li, T.L.
    In vitro characterization of enzymes involved in the synthesis of nonproteinogenic residue (2S,3S)-beta-methylphenylalanine in glycopeptide antibiotic mannopeptimycin (2009), ChemBioChem, 10, 2480-2487.
    View publication on PubMed
Search for more literature for 2.1.1.281

Cloned(Commentary)

Cloned (Comment) Organism
His6-tagged enzyme is expressed in Escherichia coli Streptomyces hygroscopicus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.014
-
 S-adenosyl-L-methionine pH 8.0, 30°C Streptomyces hygroscopicus
2.5
-
 2-oxo-3-phenylpropanoate pH 8.0, 30°C Streptomyces hygroscopicus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
S-adenosyl-L-methionine + 2-oxo-3-phenylpropanoate Streptomyces hygroscopicus 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-homocysteine + (3S)-2-oxo-3-methyl-3-phenylpropanoate
-
 ?
S-adenosyl-L-methionine + 2-oxo-3-phenylpropanoate Streptomyces hygroscopicus NRRL3085 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-homocysteine + (3S)-2-oxo-3-methyl-3-phenylpropanoate
-
 ?

Organism

Organism UniProt Comment Textmining
Streptomyces hygroscopicus
-
-
-
Streptomyces hygroscopicus NRRL3085
-
-
-

Purification (Commentary)

Purification (Comment) Organism
-
 Streptomyces hygroscopicus

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
S-adenosyl-L-methionine + 2-oxo-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 Streptomyces hygroscopicus S-adenosyl-L-homocysteine + (3S)-2-oxo-3-methyl-3-phenylpropanoate
-
 ?
S-adenosyl-L-methionine + 2-oxo-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 Streptomyces hygroscopicus S-adenosyl-L-homocysteine + (3S)-2-oxo-3-methyl-3-phenylpropanoate (3S)-2-oxo-3-methyl-3-phenylpropanoate i.e. (3S)-beta-methyl-phenylpyruvate ?
S-adenosyl-L-methionine + 2-oxo-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 Streptomyces hygroscopicus NRRL3085 S-adenosyl-L-homocysteine + (3S)-2-oxo-3-methyl-3-phenylpropanoate
-
 ?
S-adenosyl-L-methionine + 2-oxo-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 Streptomyces hygroscopicus NRRL3085 S-adenosyl-L-homocysteine + (3S)-2-oxo-3-methyl-3-phenylpropanoate (3S)-2-oxo-3-methyl-3-phenylpropanoate i.e. (3S)-beta-methyl-phenylpyruvate ?

Synonyms

Synonyms Comment Organism
MppJ
-
 Streptomyces hygroscopicus
phenylpyruvate Cbeta-methyltransferase
-
 Streptomyces hygroscopicus
phenylpyruvate methyltransferase
-
 Streptomyces hygroscopicus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.8
-
 2-oxo-3-phenylpropanoate pH 8.0, 30°C Streptomyces hygroscopicus
8.15
-
 S-adenosyl-L-methionine pH 8.0, 30°C Streptomyces hygroscopicus

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.32
-
 2-oxo-3-phenylpropanoate pH 8.0, 30°C Streptomyces hygroscopicus
582
-
 S-adenosyl-L-methionine pH 8.0, 30°C Streptomyces hygroscopicus