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Literature summary for 3.3.2.8 extracted from

  • Hou, Q.Q.; Sheng, X.; Wang, J.H.; Liu, Y.J.; Liu, C.B.
    QM/MM study of the mechanism of enzymatic limonene 1,2-epoxide hydrolysis (2011), Biochim. Biophys. Acta, 1824, 263-268.
    View publication on PubMed

Crystallization (Commentary)

Crystallization (Comment) Organism
modeling of substrate 1,2-epoxymenth-8-ene into the active site of crystal structure and evaluation of the roles of residues Arg99, Tyr53 and Asn55 by QM/MM-scannedenergy mapping Rhodococcus erythropolis

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
limonene-1,2-epoxide + H2O Rhodococcus erythropolis
-
limonene-1,2-diol
-
?
limonene-1,2-epoxide + H2O Rhodococcus erythropolis DCL14
-
limonene-1,2-diol
-
?

Organism

Organism UniProt Comment Textmining
Rhodococcus erythropolis Q9ZAG3
-
-
Rhodococcus erythropolis DCL14 Q9ZAG3
-
-

Reaction

Reaction Comment Organism Reaction ID
1,2-epoxymenth-8-ene + H2O = menth-8-ene-1,2-diol mechanism involves a concerted general acid catalysis step involving the Asp101-Arg99-Asp132 triad. The water molecule acting as nucleophilic reagent moves to the more substituted oxirane carbon atom, its hydrogen atom transfers to Asp132, and hydroxyl attacks at C1. Meanwhile, Asp101 donates a proton to the epoxide oxygen opening the oxirane ring. This process has an energy barrier of 16.9 kcal/mol and an endothermicity of 8.2 kcal/mol, and yields (1R,2R,4S)-limonene-1,2-diol as product. Activation barriers of 16.9 and 25.1 kcal/mol are calculated at the B3LYP/6-31G(d,p)//CHARMM level for nucleophilic attack on the more and less substituted epoxide carbons, respectively Rhodococcus erythropolis

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
limonene-1,2-epoxide + H2O
-
Rhodococcus erythropolis limonene-1,2-diol
-
?
limonene-1,2-epoxide + H2O
-
Rhodococcus erythropolis DCL14 limonene-1,2-diol
-
?

Synonyms

Synonyms Comment Organism
LEH
-
Rhodococcus erythropolis
limonene 1,2-epoxide hydrolase
-
Rhodococcus erythropolis