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Literature summary for 2.1.1.281 extracted from

  • Sommer-Kamann, C.; Fries, A.; Mordhorst, S.; Andexer, J.N.; Mueller, M.
    Asymmetric C-alkylation by the S-adenosylmethionine-dependent methyltransferase SgvM (2017), Angew. Chem. Int. Ed. Engl., 56, 4033-4036 .
    View publication on PubMed
Search for more literature for 2.1.1.281

Application

Application Comment Organism
synthesis the nonenzymatic stereoselective formation of C-C bonds by methylation is challenging and usually requires multistep syntheses. In contrast, the asymmetric introduction of a methyl group in natural product biosynthesis is performed in a single step and catalyzed by methyltransferases (MTs), which usually require S-adenosylmethionine (SAM) as the methyl donor. Enzyme SgvM might be a valuable tool for asymmetric biocatalytic C-alkylation reactions. It catalyze the transfer of the electrophilic methyl group of SAM to the C3 position Streptomyces griseoviridis

Cloned(Commentary)

Cloned (Comment) Organism
gene ELQ87_35210, the MT SgvM locates in the biosynthetic gene cluster of the octadepsipeptide antibiotic viridogrisein Streptomyces griseoviridis

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
S-adenosyl-L-methionine + 3-phenylpyruvate Streptomyces griseoviridis
-
 S-adenosyl-L-homocysteine + (3S)-2-oxo-3-phenylbutanoate
-
 ?
S-adenosyl-L-methionine + 4-methyl-2-oxovalerate Streptomyces griseoviridis
-
 S-adenosyl-L-homocysteine + ?
-
 ?

Organism

Organism UniProt Comment Textmining
Streptomyces griseoviridis A0A3Q9KTF8
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
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 Streptomyces griseoviridis ?
-
-
S-adenosyl-L-ethionine + 2-oxobutyrate
-
 Streptomyces griseoviridis S-adenosyl-L-homocysteine + (3S)-methyl-2-oxovalerate
-
 ?
S-adenosyl-L-methionine + 2-oxobutyrate
-
 Streptomyces griseoviridis S-adenosyl-L-homocysteine + 3-methyl-2-oxobutyrate
-
 ?
S-adenosyl-L-methionine + 2-oxovalerate
-
 Streptomyces griseoviridis S-adenosyl-L-homocysteine + (3R)-methyl-2-oxovalerate
-
 ?
S-adenosyl-L-methionine + 3-phenylpyruvate
-
 Streptomyces griseoviridis S-adenosyl-L-homocysteine + (3S)-2-oxo-3-phenylbutanoate
-
 ?
S-adenosyl-L-methionine + 4-methyl-2-oxovalerate
-
 Streptomyces griseoviridis S-adenosyl-L-homocysteine + ?
-
 ?
S-adenosyl-L-methionine + 4-methyl-2-oxovalerate
-
 Streptomyces griseoviridis S-adenosyl-L-homocysteine + 3,4-dimethyl-2-oxovalerate
-
 ?
S-adenosyl-L-methionine + pyruvate SgvM-catalyzed 13C-dimethylation of pyruvate in two steps results in formation of 3-methyl-2-oxobutyrate Streptomyces griseoviridis S-adenosyl-L-homocysteine + 2-oxobutyrate
-
 ?

Synonyms

Synonyms Comment Organism
C-MT
-
 Streptomyces griseoviridis
ELQ87_35210
-
 Streptomyces griseoviridis
MT SgvM
-
 Streptomyces griseoviridis
S-adenosylmethionine-dependent methyltransferase
-
 Streptomyces griseoviridis
SgvM
-
 Streptomyces griseoviridis

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 assay at Streptomyces griseoviridis

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8
-
 assay at Streptomyces griseoviridis

General Information

General Information Comment Organism
physiological function S-adenosylmethionine-dependent methyltransferases (MTs) play a decisive role in the biosynthesis of natural products and in epigenetic processes. MTs catalyze the methylation of heteroatoms and even of carbon atoms, which, in many cases, is a challenging reaction in conventional synthesis. C-MTs are often highly substrate-specific. SgvM from Streptomyces griseoviridis features an extended substrate scope with respect to the nucleophile as well as the electrophile. It catalyze the transfer of the electrophilic methyl group of SAM to the C3 position of 4-methyl-2-oxovalerate (alpha-ketoleucine) Streptomyces griseoviridis