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Literature summary extracted from

  • Miranda-Rojas, S.; Toro-Labbe, A.
    Mechanistic insights into the dehalogenation reaction of fluoroacetate/fluoroacetic acid (2015), J. Chem. Phys., 142, 194301.
    View publication on PubMed

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.8.1.3 fluoroacetate + H2O Rhodopseudomonas palustris
-
 glycolate + fluoride
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.8.1.3 Rhodopseudomonas palustris
-
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
3.8.1.3 haloacetate + H2O = glycolate + halide the fluoroacetate dehalogenase catalyzes fluoroacetate degradation through a two step process initiated by an SN2 reaction in which the aspartate residue performs a nucleophilic attack on the carbon bonded to the fluorine; the second step is hydrolysis that releases the product as glycolate, reaction activation and mechanism, overview. The activation of this catalytic step is associated to the interaction of the halogen with residues His155, Trp156, and Tyr219 (numbering according to PDB ID 3R3U from Rhodopseudomonas palustris), which may facilitate the Calpha-F bond dissociation Rhodopseudomonas palustris
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.8.1.3 fluoroacetate + H2O
-
 Rhodopseudomonas palustris glycolate + fluoride
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.8.1.3 fluoroacetate dehalogenase
-
 Rhodopseudomonas palustris

General Information

EC Number General Information Comment Organism
3.8.1.3 additional information density functional theory calculations of the SN2 initiation reaction modeled through the interaction between the substrate and the propionate anion as the nucleophile, the reaction energy is modulated by the degree of stabilization of the fluoride anion formed after the SN2 reaction. The activation of this catalytic step is associated to the interaction of the halogen with residues His155, Trp156, and Tyr219, which may facilitate the Calpha-F bond dissociation Rhodopseudomonas palustris
3.8.1.3 physiological function fluoroacetate dehalogenase catalyzes degradation of the environmentally toxic fluoroacetate through a two step process initiated by an SN2 reaction in which the aspartate residue performs a nucleophilic attack on the carbon bonded to the fluorine, the second step is hydrolysis that releases the product as glycolate Rhodopseudomonas palustris