1.14.13.208: benzoyl-CoA 2,3-epoxidase
This is an abbreviated version!
For detailed information about benzoyl-CoA 2,3-epoxidase, go to the full flat file.
Word Map on EC 1.14.13.208
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1.14.13.208
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evansii
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benzoate
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azoarcus
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epoxidation
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diiron
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boxc
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thioesters
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protocatechuate
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enoyl-coa
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homodimeric
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non-aromatic
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oxygenases
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coa-dependent
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succinyl-coa
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dihydrodiol
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iron-sulfur
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semialdehyde
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phenylacetyl-coa
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benzoate-induced
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diferric
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benzoate-coa
- 1.14.13.208
- evansii
- benzoate
-
azoarcus
-
epoxidation
-
diiron
- boxc
- thioesters
- protocatechuate
- enoyl-coa
-
homodimeric
-
non-aromatic
- oxygenases
-
coa-dependent
- succinyl-coa
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dihydrodiol
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iron-sulfur
- semialdehyde
- phenylacetyl-coa
-
benzoate-induced
-
diferric
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benzoate-coa
Reaction
Synonyms
benzoyl coenzyme A epoxidase, benzoyl-CoA 2,3-dioxygenase, benzoyl-CoA dioxygenase/reductase, benzoyl-CoA epoxidase, benzoyl-CoA oxygenase, benzoyl-coenzyme A epoxidase, BoxA, BoxA/BoxB system, BoxAB, BoxB, BoxBA, EC 1.14.12.21
ECTree
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Reaction
Reaction on EC 1.14.13.208 - benzoyl-CoA 2,3-epoxidase
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benzoyl-CoA + NADPH + H+ + O2 = 2,3-epoxy-2,3-dihydrobenzoyl-CoA + NADP+ + H2O
epoxidation starts with the binding of the O2 molecule to the diferrous center to generate a diferric peroxide complex, followed by concerted O-O bond cleavage and epoxide formation. Two different pathways have been located, leading to (2S,3R)-epoxy and (2R,3S)-epoxy products. The barrier difference is 2.8 kcal/mol, corresponding to a diastereomeric excess of about 99:1. Further isomerization from epoxide to phenol has quite a high barrier, which cannot compete with the product release step. After product release into solution, fast epoxide-oxepin isomerization and racemization can take place easily, leading to a racemic mixture of (2S,3R) and (2R,3S) products. The deoxygenation of epoxide to regenerate benzoyl-CoA by a diferrous form of the enzyme proceeds via a stepwise mechanism. The C2-O bond cleavage happens first, coupled with one electron transfer from one iron center to the substrate, to form a radical intermediate, which is followed by the second C3-O bond cleavage. The first step is rate-limiting. Reaction mechanism, modeling and simulations, detailed overview
benzoyl-CoA + NADPH + H+ + O2 = 2,3-epoxy-2,3-dihydrobenzoyl-CoA + NADP+ + H2O
molecular reaction mechanism analysis, different pathways are possible, detailed overview
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benzoyl-CoA + NADPH + H+ + O2 = 2,3-epoxy-2,3-dihydrobenzoyl-CoA + NADP+ + H2O
molecular reaction mechanism analysis, different pathways are possible, detailed overview
Aromatoleum evansii KB 740
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