The title compound, C14H17NO4, features an epoxide-O atom fused to a pyrrolidyl ring, the latter having an envelope conformation with the N atom being the flap. The 4-meth-oxy-phenyl group is orthogonal to [dihedral angle = 85.02 (6)°] and lies to the opposite side of the five-membered ring to the epoxide O atom, while the N-bound ethyl ester group (r.m.s. deviation of the five fitted atoms = 0...

Epoxide hydrolases catalyze hydrolytic epoxide ring-opening, most often via formation of a covalent hydroxyalkyl-enzyme intermediate. A mutant of Agrobacterium radiobacter epoxide hydrolase, in which the phenylalanine residue that flanks the invariant catalytic aspartate nucleophile is replaced by a threonine, exhibited inactivation during conversion when the (R)-enantiomer of para-nitrostyrene...

Benzo[a]pyrene 7,8-diol 9,10-epoxide adducts in DNA are implicated in mutagenesis, and their formation from the diol epoxides and subsequent incorrect replication by human DNA polymerases provide an attractive mechanism for the induction of cancer by this highly carcinogenic hydrocarbon and its diol epoxide metabolites. Here, we describe the crystal structure of such an adduct at the exocyclic ...

s for posters:Experimental Biology 2008, San Diego, April 2008IDENTIFICATION OF A NEW POTENTIAL HUMAN EPOXIDE HYDROLASE(NEH2)Martina Decker, Magdalena Adamska, Michael Arand. Leopoldina Symposium of Lipid Signaling, Frankfurt, September 2008CHARACTERIZATION OF A NOVEL HUMAN EPOXIDE HYDROLASE (EH3)CAPABLE OF CONVERTING EPOXYEICOSATRIENOIC ACIDS (EETS)Martina Decker, M...

Epoxide hydrolases catalyze hydrolytic epoxide ringopening, most often via formation of a covalent hydroxyalkyl-enzyme intermediate. A mutant of Agrobacterium radiobacter epoxide hydrolase, in which the phenylalanine residue that flanks the invariant catalytic aspartate nucleophile is replaced by a threonine, exhibited inactivation during conversion when the (R)-enantiomer of para-nitrostyrene ...

Coumarin is used widely as a fragrance constituent and is administered clinically in the treatment of certain lymphedemas and malignancies. Although toxicity occurs only rarely in humans treated clinically with high-dose coumarin, it is well established that coumarin is hepatotoxic in the rat. This species difference in susceptibility to toxicity reflects the disparate metabolic processes occur...

Four glutathione transferases (EC 2.5.1.18), glutathione transferases A, B, and C and a hitherto unknown form, termed X, were purified to apparent homogeneity from rat liver cytosol. They were investigated for their abilities to inactivate two mutagenic epoxides derived from the polycyclic aromatic hydrocarbon benz(a)anthracene, the K-region epoxide benz(a)anthracene 5,6-oxide and the diol-epox...

Metabolism of the (+)-(3S,4S)and (-)-(3R,4R)-enantiomers of trnns-3,4-dihydroxy-3,4-dihydrobenz[a]anthracene has been examined with liver microsomes from control rats, as well as rats treated with 3-methylcholanthrene or phenobarbital and by a highly purified and reconstituted system containing cytochrome P-450, and epoxide hydrolase. In contrast to the metabolism of the related (-)-benzo[a]pyr...

Epoxyeicosatrienoic acids are cytochrome P-450 metabolites of arachidonic acid with multiple biological functions, including the regulation of vascular tone, renal tubular transport, cellular proliferation, and inflammation. Epoxyeicosatrienoic acids are converted by soluble epoxide hydrolase into the corresponding dihydroxyeicosatrienoic acids, and epoxyeicosatrienoic acid hydration is regarde...

Two substrates, 1-(4’-ethylphenoxy)-3,7-dimethyl-6,7-epoxy-trans-2-octene and cis-epoxymethyl stearate were used to determine the distribution of epoxide hydrase activity in mammals. The highest epoxide hydrase activity in liver subcellular fractions was found in the 100,000 g supernatant and the mitochondrial fraction, while activity in washed microsomes is lower. The 100,000 g supernatant epo...