Molecular cloning and expression of a 2-arylpropionyl-coenzyme A epimerase: a key enzyme in the inversion metabolism of ibuprofen.
@article{Reichel1997MolecularCA, title={Molecular cloning and expression of a 2-arylpropionyl-coenzyme A epimerase: a key enzyme in the inversion metabolism of ibuprofen.}, author={C. Reichel and R. Brugger and H. Bang and G. Geisslinger and K. Brune}, journal={Molecular pharmacology}, year={1997}, volume={51 4}, pages={ 576-82 } }
The 2-arylpropionic acid derivatives, including ibuprofen, are the most widely used anti-inflammatory analgesic cyclooxygenase inhibitors. The (-)-R-enantiomer, which is inactive in terms of cyclooxygenase inhibition, is epimerized in vivo via the 2-arylpropionyl-coenzyme A (CoA) epimerase to the cyclooxygenase-inhibiting (+)-S-enantiomer. The molecular biology of the epimerization pathway is largely unknown. To clarify this mechanism, the sequence of the 2-arylpropionyl-CoA epimerase was… CONTINUE READING
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References
SHOWING 1-10 OF 45 REFERENCES
2-Arylpropionyl-CoA epimerase: partial peptide sequences and tissue localization.
- Biology, Medicine
- Biochemical pharmacology
- 1995
- 26
Purification and characterization of novel "2-arylpropionyl-CoA epimerases" from rat liver cytosol and mitochondria.
- Biology, Medicine
- The Journal of biological chemistry
- 1993
- 73
- Highly Influential
- PDF
The role of coenzyme A in the biotransformation of 2-arylpropionic acids.
- Chemistry, Medicine
- Chemico-biological interactions
- 1994
- 39
Microbial metabolism of 2-arylpropionic acids: chiral inversion of ibuprofen and 2-phenylpropionic acid.
- Chemistry, Medicine
- Chirality
- 1993
- 24
Chiral inversion of 2-arylpropionic acid non-steroidal anti-inflammatory drugs--II. Racemization and hydrolysis of (R)- and (S)-ibuprofen-CoA thioesters.
- Chemistry, Medicine
- Biochemical pharmacology
- 1991
- 60
Metabolic inversion of (R)-ibuprofen. Epimerization and hydrolysis of ibuprofenyl-coenzyme A.
- Chemistry, Medicine
- Drug metabolism and disposition: the biological fate of chemicals
- 1992
- 55
Metabolic chiral inversion of 2-arylpropionates in rat H4IIE and human Hep G2 hepatoma cells. Relationship to in vivo metabolism.
- Biology, Chemistry
- Biochemical pharmacology
- 1992
- 15
Isolation and characterization of rat liver microsomal R-ibuprofenoyl-CoA synthetase.
- Chemistry, Medicine
- Biochemical pharmacology
- 1996
- 33
The metabolic chiral inversion and dispositional enantioselectivity of the 2-arylpropionic acids and their biological consequences.
- Chemistry, Medicine
- Biochemical pharmacology
- 1988
- 355
- Highly Influential