2.1.1.308: cytidylyl-2-hydroxyethylphosphonate methyltransferase

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For detailed information about cytidylyl-2-hydroxyethylphosphonate methyltransferase, go to the full flat file.

Reaction

2 S-adenosyl-L-methionine +

Synonyms

(S)-2-hydroxyethylphosphonate methylase, 2-hydroxyethylphosphonate methyltransferase, fom3, methyltransferase fom3

ECTree

     2 Transferases

         2.1 Transferring one-carbon groups

             2.1.1 Methyltransferases

                2.1.1.308 cytidylyl-2-hydroxyethylphosphonate methyltransferase

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Results	in table
69	AA Sequence
3	Cloned(Commentary)
5	Cofactor
1	General Information
2	Metals/Ions
2	Molecular Weight [Da]
3	Natural Substrates/ Products (Substrates)
11	Organism
4	Pathway
7	Protein Variants
1	Purification (Commentary)
3	Reaction
11	Reference
11	Substrates and Products (Substrate)
3	Subunits
9	Synonyms
1	Systematic Name

Reaction

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Reaction on EC 2.1.1.308 - cytidylyl-2-hydroxyethylphosphonate methyltransferase

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REACTION

REACTION DIAGRAM

COMMENTARY

ORGANISM

UNIPROT

LITERATURE

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

3 entries

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

D2SNF5

703345

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: one electron is transferred from the reduced iron–sulfur cluster to S-adenosyl-L-methionine to form an adenosyl radical and methionine. The adenosyl radical abstracts the pro-R hydrogen atom from C2 of (S)-2-hydroxyethylphosphonate, and the resulting substrate radical reacts with methylcobalamin yielding (S)-2-hydroxypropylphosphonate and cob(II)alamin. The enzyme is then returned to the active state by reduction of the 4Fe4S cluster back to the +1 state and binding of S-adenosyl-L-methionine and methylcobalamin. Alternatively, cob(II)alamin might be reduced to cob(I)alamin and methylated while bound to the enzyme

Streptomyces fradiae

D2SNF5

703183

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

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