Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 3.8.1.3 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
Search for more literature for 3.8.1.3

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Rhodopseudomonas palustris
-
-
-

Reaction

Reaction Comment Organism Reaction ID
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)

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

Synonyms

Synonyms Comment Organism
fluoroacetate dehalogenase
-
 Rhodopseudomonas palustris

General Information

General Information Comment Organism
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
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