Hydrolases;
Acting on ether bonds;
Ether hydrolases
BRITE hierarchy

cis-stilbene-oxide hydrolase

(1) cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol [RN:R07627];
(2) 1-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]methanamine + H2O = 2-({[(4-methoxyphenyl)methyl](methyl)amino}methyl)-2-methylpropane-1,3-diol [RN:R11930]

R07627 R11930;
(other) R07013 R07014 R07027 R07071 R07072 R07082 R09410 R09417 R09443
Reaction

cis-stilbene oxide [CPD:C16014];
H2O [CPD:C00001];
1-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]methanamine [CPD:C21775]

This is a key hepatic enzyme that catalyses the hydrolytic ring opening of oxiranes (epoxides) and oxetanes to give the corresponding diols. The enzyme is involved in the metabolism of numerous substrates including the stereoselective hydrolytic ring opening of 7-oxabicyclo[4.1.0]hepta-2,4-dienes (arene oxides) to the corresponding trans-dihydrodiols. The reaction proceeds via a triad mechanism and involves the formation of an hydroxyalkyl-enzyme intermediate. Five epoxide-hydrolase enzymes have been identified in vertebrates to date: EC 3.3.2.6 (leukotriene-A4 hydrolase), EC 3.3.2.7 (hepoxilin-epoxide hydrolase), EC 3.3.2.9 (microsomal epoxide hydrolase), EC 3.3.2.10 (soluble epoxide hydrolase) and EC 3.3.2.11 (cholesterol-5,6-oxide hydrolase).

EC 3.3.2.9 created 2006 (EC 3.3.2.3 created 1978, modified 1999, part incorporated 2006), modified 2017

1  [PMID:4998715]

2

3  [PMID:4584115]

4  [PMID:4463951]

5  [PMID:240858]

6  [PMID:7986671]

7  [PMID:11154734]

8  [PMID:15822179]

9  [PMID:15748653]

10 [PMID:28600384]