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Literature summary for 2.1.1.308 extracted from

  • Booker, S.J.
    Anaerobic functionalization of unactivated C-H bonds (2009), Curr. Opin. Chem. Biol., 13, 58-73.
    View publication on PubMedView publication on EuropePMC
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Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(2-hydroxyethyl)phosphonate + S-adenosyl-L-methionine + methylcobalamin Streptomyces fradiae Fom3 catalyzes the penultimate step in the biosynthesis of fosfomycin, an antibiotic produced by several species of Streptomyces and Pseudomonas (S)-2-hydroxypropylphosphonate + L-methionine + 5'-deoxyadenosine + cob(II)alamin
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Organism

Organism UniProt Comment Textmining
Streptomyces fradiae D2SNF5
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Reaction

Reaction Comment Organism Reaction ID
2 S-adenosyl-L-methionine + cytidine 5'-{[hydroxy(2-hydroxyethyl)phosphonoyl]phosphate} + reduced acceptor = S-adenosyl-L-homocysteine + 5'-deoxyadenosine + L-methionine + cytidine 5'-{[hydroxy(2-hydroxypropyl)phosphonoyl]phosphate} + oxidized acceptor proposed mechanism: a 5'-deoxyadenosine radical generated from reductive cleavage of S-adenosyl-L-methionine is used to abstract the hydrogen atom from the C-H bond of the substrate resulting in a substrate radical that reacts with methylcobalamin yielding (S)-2-hydroxypropylphosphonate and cob(II)alamin Streptomyces fradiae
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(2-hydroxyethyl)phosphonate + S-adenosyl-L-methionine + methylcobalamin Fom3 catalyzes the penultimate step in the biosynthesis of fosfomycin, an antibiotic produced by several species of Streptomyces and Pseudomonas Streptomyces fradiae (S)-2-hydroxypropylphosphonate + L-methionine + 5'-deoxyadenosine + cob(II)alamin
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 ?
(2-hydroxyethyl)phosphonate + S-adenosyl-L-methionine + methylcobalamin C-2 methylation of hydroxyethyl phosphonate Streptomyces fradiae (S)-2-hydroxypropylphosphonate + L-methionine + 5'-deoxyadenosine + cob(II)alamin
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Synonyms

Synonyms Comment Organism
fom3
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 Streptomyces fradiae

Cofactor

Cofactor Comment Organism Structure
methylcobalamin proposed mechanism: a 5'-deoxyadenosine radical generated from reductive cleavage of S-adenosyl-L-methionine is used to abstract the hydrogen atom from the C-H bond of the substrate resulting in a substrate radical that reacts with methylcobalamin yielding (S)-2-hydroxypropylphosphonate and cob(II)alamin Streptomyces fradiae
S-adenosyl-L-methionine proposed mechanism: a 5'-deoxyadenosine radical generated from reductive cleavage of S-adenosyl-L-methionine is used to abstract the hydrogen atom from the C-H bond of the substrate resulting in a substrate radical that reacts with methylcobalamin yielding (S)-2-hydroxypropylphosphonate and cob(II)alamin Streptomyces fradiae