エポキシドヒドロラーゼ
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/10/06 16:12:47」(JST)
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| microsomal epoxide hydrolase |
| Identifiers |
| EC number |
3.3.2.9 |
| CAS number |
9048-63-9 |
| Databases |
| IntEnz |
IntEnz view |
| BRENDA |
BRENDA entry |
| ExPASy |
NiceZyme view |
| KEGG |
KEGG entry |
| MetaCyc |
metabolic pathway |
| PRIAM |
profile |
| PDB structures |
RCSB PDB PDBe PDBsum |
| Gene Ontology |
AmiGO / EGO |
| Search |
| PMC |
articles |
| PubMed |
articles |
| NCBI |
proteins |
|
| soluble epoxide hydrolase |
|
Epoxide hydrolase from Mycobacterium tuberculosis.[1]
|
| Identifiers |
| EC number |
3.3.2.10 |
| CAS number |
9048-63-9 |
| Databases |
| IntEnz |
IntEnz view |
| BRENDA |
BRENDA entry |
| ExPASy |
NiceZyme view |
| KEGG |
KEGG entry |
| MetaCyc |
metabolic pathway |
| PRIAM |
profile |
| PDB structures |
RCSB PDB PDBe PDBsum |
| Gene Ontology |
AmiGO / EGO |
| Search |
| PMC |
articles |
| PubMed |
articles |
| NCBI |
proteins |
|
Epoxide hydrolase (also known as epoxide hydratase) functions in detoxification during drug metabolism. It converts epoxides to trans-dihydrodiols, which can be conjugated and excreted from the body. Epoxides result from the degradation of aromatic compounds. Deficiency in this enzyme in patients receiving aromatic-type anti-epileptic drugs such as phenytoin is reported to lead to DRESS syndrome.
Epoxides are significant as cytochrome P450 oxidase metabolites of unsaturated carbon-carbon bonds, but are also mutagenic. Epoxide hydrolase is present in large quantity on endoplasmic reticulum.
Contents
- 1 Drug target
- 2 Isozymes
- 3 References
- 4 External links
Drug target
Mycobacterium tuberculosis, the major causative agent of tuberculosis, expresses at least six different forms of epoxide hydrolase (forms A-F). The structure of epoxide hydrolase B reveals that the enzyme is a monomer and contains an alpha/beta hydrolase fold. In addition to providing insights into the enzyme mechanism, this hydrolase currently serves as a platform for rational drug design of potent inhibitors. In particular, urea based inhibitors have been developed. These inhibitors directly target the catalytic cavity. It is hypothesized that the structure of epoxide hydrolase B may allow for drug design to inhibit all other Mycobacterium tuberculosis hydrolases as long as they contain similar alpha/beta folds.
The structure of hydrolase B contains a cap domain, which is hypothesized to regulate the active site of the hydrolase.[1] Furthermore, Asp104, His333, and Asp302 form the catalytic triad of the protein and is critical to function of the protein.
At present, other structures of Mycobacterium tuberculosis hydrolase have not been solved.
Isozymes
Humans express the following four isozymes of epoxide hydrolase:
| epoxide hydrolase 1, microsomal |
| Identifiers |
| Symbol |
EPHX1 |
| Entrez |
2052 |
| HUGO |
3401 |
| OMIM |
132810 |
| RefSeq |
NM_000120 |
| UniProt |
Q9NQV0 |
| Other data |
| Locus |
Chr. 1 q42.1 |
|
| epoxide hydrolase 2, cytoplasmic |
| Identifiers |
| Symbol |
EPHX2 |
| Entrez |
2053 |
| HUGO |
3402 |
| OMIM |
132811 |
| RefSeq |
NM_001979 |
| UniProt |
P34913 |
| Other data |
| Locus |
Chr. 8 p21 |
|
| epoxide hydrolase 3 |
| Identifiers |
| Symbol |
EPHX3 |
| Alt. symbols |
ABHD9 |
| Entrez |
79852 |
| HUGO |
23760 |
| RefSeq |
NM_024794 |
| UniProt |
Q9H6B9 |
| Other data |
| Locus |
Chr. 19 p13.13 |
|
| epoxide hydrolase 4 |
| Identifiers |
| Symbol |
EPHX4 |
| Alt. symbols |
ABHD7 |
| Entrez |
253152 |
| HUGO |
23758 |
| RefSeq |
NM_173567 |
| UniProt |
Q8IUS5 |
| Other data |
| Locus |
Chr. 1 p22.1 |
|
References
- ^ a b PDB 2E3J; Biswal BK, Morisseau C, Garen G, Cherney MM, Garen C, Niu C, Hammock BD, James MN. (September 2008). "The molecular structure of epoxide hydrolase B from Mycobacterium tuberculosis and its complex with a urea-based inhibitor.". J. Mol. Bio. 381 (4): 897–912. doi:10.1016/j.jmb.2008.06.030. PMC 2866126. PMID 18585390. ; rendered via PyMOL
External links
- Epoxide hydrolases at the US National Library of Medicine Medical Subject Headings (MeSH)
- Epoxide hydrolase characterization and purification
|
Hydrolases: ether bond (EC 3.3)
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|
| 3.3.1 |
|
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| 3.3.2 |
- Epoxide hydrolase
- Leukotriene-A4 hydrolase
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- B
- enzm
- 1.1
- 2
- 3
- 4
- 5
- 6
- 7
- 8
- 10
- 11
- 13
- 14
- 15-18
- 2.1
- 3.1
- 4.1
- 5.1
- 6.1-3
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UpToDate Contents
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English Journal
- A sensitive LC-MS/MS method for the quantification of regioisomers of epoxyeicosatrienoic and dihydroxyeicosatrienoic acids in human plasma during endothelial stimulation.
- Duflot T1,2,3, Pereira T1, Roche C2,3, Iacob M1, Cardinael P4, Hamza NE4, Thuillez C1,2,3, Compagnon P1, Joannidès R1,2,3, Lamoureux F1,2,3, Bellien J5,6,7.
- Analytical and bioanalytical chemistry.Anal Bioanal Chem.2017 Mar;409(7):1845-1855. doi: 10.1007/s00216-016-0129-1. Epub 2016 Dec 15.
- Epoxyeicosatrienoic acids (EETs) are vasodilating lipid mediators metabolized into dihydroxyeicosatrienoic acids (DHETs) by soluble epoxide hydrolase. We aimed to develop a LC-MS/MS method to quantify EETs and DHETs in human plasma and monitored their levels during vascular endothelial stimulation.
- PMID 27981341
- Enhancing productivity for cascade biotransformation of styrene to (S)-vicinal diol with biphasic system in hollow fiber membrane bioreactor.
- Gao P1,2, Wu S1,2, Praveen P1, Loh KC1, Li Z3,4.
- Applied microbiology and biotechnology.Appl Microbiol Biotechnol.2017 Mar;101(5):1857-1868. doi: 10.1007/s00253-016-7954-1. Epub 2016 Nov 9.
- Biotransformation is a green and useful tool for sustainable and selective chemical synthesis. However, it often suffers from the toxicity and inhibition from organic substrates or products. Here, we established a hollow fiber membrane bioreactor (HFMB)-based aqueous/organic biphasic system, for the
- PMID 27830295
- Hybrid Receptor-Bound/MM-GBSA-Per-residue Energy-Based Pharmacophore Modelling: Enhanced Approach for Identification of Selective LTA4H Inhibitors as Potential Anti-inflammatory Drugs.
- Appiah-Kubi P1, Soliman M2.
- Cell biochemistry and biophysics.Cell Biochem Biophys.2017 Mar;75(1):35-48. doi: 10.1007/s12013-016-0772-3. Epub 2016 Dec 2.
- Leukotriene A4 hydrolase has been identified as an enzyme with dual anti- and pro-inflammatory role, thus, the conversion of leukotriene to leukotriene B4 in the initiation stage of inflammation and the removal of the chemotactic Pro-Gly-Pro tripeptide. These findings make leukotriene A4 hydrolase a
- PMID 27914004
Japanese Journal
- Enantioselective hydrolysis of racemic epichlorohydrin using an epoxide hydrolase from Novosphingobium aromaticivorans(ENZYMOLOGY, PROTEIN ENGINEERING, AND ENZYME TECHNOLOGY)
- Woo Jung-Hee,Hwang Young-Ok,Kang Ji-Hyun,Lee Hyun Sook,Kim Sang-Jin,Kang Sung Gyun
- Journal of bioscience and bioengineering 110(3), 295-297, 2010-09
- … Previously we reported that an epoxide hydrolase (EHase) from Novosphingobium aromaticivorans could preferentially hydrolyze (R)-styrene oxide. …
- NAID 110007730018
Related Links
- Epoxide hydrolase (also known as epoxide hydratase) functions in detoxication during drug metabolism. It converts epoxides to trans-dihydrodiols, which can be conjugated and excreted from the body. Epoxides result from the degradation of ...
- Soluble epoxide hydrolase (sEH) is a bifunctional enzyme that in humans is encoded by the EPHX2 gene. sEH us a member of the epoxide hydrolase family. This enzyme, found in both the cytosol and peroxisomes, binds to specific epoxides ...
★リンクテーブル★
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- 英
- epoxide hydrolase EH, epoxide hydrolases EHs
- 同
- エポキシド加水分解酵素
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エポキシドヒドロラーゼ epoxide hydrolase EH
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エポキシドヒドロラーゼ
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