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Literature summary for 2.1.1.326 extracted from

  • Werner, W.J.; Allen, K.D.; Hu, K.; Helms, G.L.; Chen, B.S.; Wang, S.C.
    In vitro phosphinate methylation by PhpK from Kitasatospora phosalacinea (2011), Biochemistry, 50, 8986-8988.
    View publication on PubMedView publication on EuropePMC

Metals/Ions

Metals/Ions Comment Organism Structure
[4Fe-4S] center the enzyme is a radical S-adenosyl-L-methionine enzyme that contains a [4Fe-4S] center and a methylcob(III)alamin cofactor. According to the proposed mechanism, the reduced iron-sulfur center donates an electron to S-adenosyl-L-methionine, resulting in homolytic cleavage of the carbon-sulfur bond to form a 5'-deoxyadenosyl radical that abstracts the hydrogen atom from the P-H bond of the substrate, forming a phosphinate-centered radical. This radical reacts with methylcob(III)alamin to produce the methylated product and cob(II)alamin, which is reduced by an unknown donor to cob(I)alamin. A potential route for restoring the latter back to methylcob(III)alamin is a nucleophilic attack on a second S-adenosyl-L-methionine molecule Kitasatospora phosalacinea

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2 S-adenosyl-L-methionine + N-acetyldemethylphosphinothricin + reduced acceptor Kitasatospora phosalacinea N-acetyldemethylphosphinothricin i.e. (2S)-2-acetamido-4-phosphinatobutanoate. In vivo the enzyme acts on N-acetyldemethylphosphinothricin-L-alanyl-L-alanine or N-acetyl-demethylphosphinothricin-L-alanyl-L-leucine, the intermediates in the biosynthesis of the tripeptides bialaphos and phosalacine (which inhibit plant and bacterial glutamine synthetases) S-adenosyl-L-homocysteine + 5'-deoxyadenosine + L-methionine + N-acetylphosphinothricin + oxidized acceptor
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Organism

Organism UniProt Comment Textmining
Kitasatospora phosalacinea A0A059U454
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2 S-adenosyl-L-methionine + N-acetyldemethylphosphinothricin + reduced acceptor N-acetyldemethylphosphinothricin i.e. (2S)-2-acetamido-4-phosphinatobutanoate. In vivo the enzyme acts on N-acetyldemethylphosphinothricin-L-alanyl-L-alanine or N-acetyl-demethylphosphinothricin-L-alanyl-L-leucine, the intermediates in the biosynthesis of the tripeptides bialaphos and phosalacine (which inhibit plant and bacterial glutamine synthetases) Kitasatospora phosalacinea S-adenosyl-L-homocysteine + 5'-deoxyadenosine + L-methionine + N-acetylphosphinothricin + oxidized acceptor
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2 S-adenosyl-L-methionine + N-acetyldemethylphosphinothricin + reduced acceptor N-acetyldemethylphosphinothricin i.e. (2S)-2-acetamido-4-phosphinatobutanoate Kitasatospora phosalacinea S-adenosyl-L-homocysteine + 5'-deoxyadenosine + L-methionine + N-acetylphosphinothricin + oxidized acceptor
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Synonyms

Synonyms Comment Organism
PhpK
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Kitasatospora phosalacinea

Cofactor

Cofactor Comment Organism Structure
methylcob(III)alamin the enzyme is a radical S-adenosyl-L-methionine enzyme that contains a [4Fe-4S] center and a methylcob(III)alamin cofactor. According to the proposed mechanism, the reduced iron-sulfur center donates an electron to S-adenosyl-L-methionine, resulting in homolytic cleavage of the carbon-sulfur bond to form a 5'-deoxyadenosyl radical that abstracts the hydrogen atom from the P-H bond of the substrate, forming a phosphinate-centered radical. This radical reacts with methylcob(III)alamin to produce the methylated product and cob(II)alamin, which is reduced by an unknown donor to cob(I)alamin. A potential route for restoring the latter back to methylcob(III)alamin is a nucleophilic attack on a second S-adenosyl-L-methionine molecule Kitasatospora phosalacinea