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Literature summary 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

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.1.1.281 His6-tagged enzyme is expressed in Escherichia coli Streptomyces hygroscopicus
2.6.1.107 expression in Escherichia coli Streptomyces hygroscopicus

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.1.1.281 0.014
-
 S-adenosyl-L-methionine pH 8.0, 30°C Streptomyces hygroscopicus
2.1.1.281 2.5
-
 2-oxo-3-phenylpropanoate pH 8.0, 30°C Streptomyces hygroscopicus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.1.1.281 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
-
 ?
2.1.1.281 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
-
 ?
2.6.1.107 (2S,3S)-3-methylphenylalanine + 2-oxoglutarate Streptomyces hygroscopicus the enzyme is involved in the biosynthesis of the glycopeptide antibiotic mannopeptimycin (3S)-2-oxo-3-phenylbutanoate + L-glutamate
-
 ?
2.6.1.107 (2S,3S)-3-methylphenylalanine + 2-oxoglutarate Streptomyces hygroscopicus NRRL3085 the enzyme is involved in the biosynthesis of the glycopeptide antibiotic mannopeptimycin (3S)-2-oxo-3-phenylbutanoate + L-glutamate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.1.1.281 Streptomyces hygroscopicus
-
-
-
2.1.1.281 Streptomyces hygroscopicus NRRL3085
-
-
-
2.6.1.107 Streptomyces hygroscopicus Q643C8
-
-
2.6.1.107 Streptomyces hygroscopicus NRRL3085 Q643C8
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.1.1.281
-
 Streptomyces hygroscopicus

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.1.1.281 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
-
 ?
2.1.1.281 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 ?
2.1.1.281 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
-
 ?
2.1.1.281 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 ?
2.6.1.107 (2S,3S)-3-methylphenylalanine + 2-oxoglutarate
-
 Streptomyces hygroscopicus (3S)-2-oxo-3-phenylbutanoate + L-glutamate
-
 ?
2.6.1.107 (2S,3S)-3-methylphenylalanine + 2-oxoglutarate the enzyme is involved in the biosynthesis of the glycopeptide antibiotic mannopeptimycin Streptomyces hygroscopicus (3S)-2-oxo-3-phenylbutanoate + L-glutamate
-
 ?
2.6.1.107 (2S,3S)-3-methylphenylalanine + 2-oxoglutarate
-
 Streptomyces hygroscopicus NRRL3085 (3S)-2-oxo-3-phenylbutanoate + L-glutamate
-
 ?
2.6.1.107 (2S,3S)-3-methylphenylalanine + 2-oxoglutarate the enzyme is involved in the biosynthesis of the glycopeptide antibiotic mannopeptimycin Streptomyces hygroscopicus NRRL3085 (3S)-2-oxo-3-phenylbutanoate + L-glutamate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.1.1.281 MppJ
-
 Streptomyces hygroscopicus
2.1.1.281 phenylpyruvate Cbeta-methyltransferase
-
 Streptomyces hygroscopicus
2.1.1.281 phenylpyruvate methyltransferase
-
 Streptomyces hygroscopicus
2.6.1.107 TyrB
-
 Streptomyces hygroscopicus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.6.1.107 25
-
 assay at Streptomyces hygroscopicus

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2.1.1.281 0.8
-
 2-oxo-3-phenylpropanoate pH 8.0, 30°C Streptomyces hygroscopicus
2.1.1.281 8.15
-
 S-adenosyl-L-methionine pH 8.0, 30°C Streptomyces hygroscopicus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.6.1.107 8
-
 assay at Streptomyces hygroscopicus

Cofactor

EC Number Cofactor Comment Organism Structure
2.6.1.107 pyridoxal 5'-phosphate required Streptomyces hygroscopicus

General Information

EC Number General Information Comment Organism
2.6.1.107 physiological function the enzyme is involved in the biosynthesis of the glycopeptide antibiotic mannopeptimycin Streptomyces hygroscopicus

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
2.1.1.281 0.32
-
 2-oxo-3-phenylpropanoate pH 8.0, 30°C Streptomyces hygroscopicus
2.1.1.281 582
-
 S-adenosyl-L-methionine pH 8.0, 30°C Streptomyces hygroscopicus