Microsomal epoxide hydrolase
| Microsomal epoxide hydrolase | |||||||||
|---|---|---|---|---|---|---|---|---|---|
| Identifiers | |||||||||
| EC number | 3.3.2.9 | ||||||||
| Databases | |||||||||
| IntEnz | IntEnz view | ||||||||
| BRENDA | BRENDA entry | ||||||||
| ExPASy | NiceZyme view | ||||||||
| KEGG | KEGG entry | ||||||||
| MetaCyc | metabolic pathway | ||||||||
| PRIAM | profile | ||||||||
| PDB structures | RCSB PDB PDBe PDBsum | ||||||||
| |||||||||
In enzymology, a microsomal epoxide hydrolase (EC 3.3.2.9) is an enzyme that catalyzes the chemical reaction
- cis-stilbene oxide + H2O (+)-(1R,2R)-1,2-diphenylethane-1,2-diol
Thus, the two substrates of this enzyme are cis-stilbene oxide and H2O, whereas its product is (+)-(1R,2R)-1,2-diphenylethane-1,2-diol.
This enzyme belongs to the family of hydrolases, specifically those acting on ether bonds (ether hydrolases). The systematic name of this enzyme class is cis-stilbene-oxide hydrolase. Other names in common use include epoxide hydratase (ambiguous), microsomal epoxide hydratase (ambiguous), epoxide hydrase, microsomal epoxide hydrase, arene-oxide hydratase (ambiguous), benzo[a]pyrene-4,5-oxide hydratase, benzo(a)pyrene-4,5-epoxide hydratase, aryl epoxide hydrase (ambiguous), cis-epoxide hydrolase, and mEH. This enzyme participates in metabolism of xenobiotics by cytochrome p450.
This class of enzymes plays a role in the uptake of bile salts within the large intestine. It functions as a Na+ dependent transporter.
References
- Boyer, P.D. (Ed.), The Enzymes, 3rd ed., vol. 7, Academic Press, New York, 1972, p. 199-212.
- Lu AY, Ryan D, Jerina DM, Daly JW, Levin W (1975). "Liver microsomal expoxide hydrase. Solubilization, purification, and characterization". J. Biol. Chem. 250 (20): 8283–8. PMID 240858.
- Oesch F (1974). "Purification and specificity of a human microsomal epoxide hydratase". Biochem. J. 139 (1): 77–88. doi:10.1042/bj1390077. PMC 1166253
. PMID 4463951. - Oesch F, Daly J (1971). "Solubilization, purification, and properties of a hepatic epoxide hydrase". Biochim. Biophys. Acta. 227 (3): 692–7. doi:10.1016/0005-2744(71)90018-0. PMID 4998715.
- Bellucci G, Chiappe C, Ingrosso G (1994). "Kinetics and stereochemistry of the microsomal epoxide hydrolase-catalyzed hydrolysis of cis-stilbene oxides". Chirality. 6 (7): 577–82. doi:10.1002/chir.530060711. PMID 7986671.
- Morisseau C, Hammock BD (2005). "Epoxide hydrolases: mechanisms, inhibitor designs, and biological roles". Annu. Rev. Pharmacol. Toxicol. 45: 311–33. doi:10.1146/annurev.pharmtox.45.120403.095920. PMID 15822179.
- Fretland AJ, Omiecinski CJ (2000). "Epoxide hydrolases: biochemistry and molecular biology". Chem. Biol. Interact. 129 (1–2): 41–59. doi:10.1016/S0009-2797(00)00197-6. PMID 11154734.
- Oesch F (1973). "Mammalian epoxide hydrases: inducible enzymes catalysing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds". Xenobiotica. 3 (5): 305–40. doi:10.3109/00498257309151525. PMID 4584115.
- Lacourciere GM, Armstrong RN (1994). "Microsomal and soluble epoxide hydrolases are members of the same family of C-X bond hydrolase enzymes". Chem. Res. Toxicol. 7 (2): 121–4. doi:10.1021/tx00038a001. PMID 8199297.
- Newman JW, Morisseau C, Hammock BD (2005). "Epoxide hydrolases: their roles and interactions with lipid metabolism". Prog. Lipid. Res. 44 (1): 1–51. doi:10.1016/j.plipres.2004.10.001. PMID 15748653.