Rapid screening of enzymes for the enzymatic hydrolysis of chiral esters in drug discovery

Chirality

Volumn 19, Issue 9, 2007, Pages 701-705

  Petucci, Chris ^a   Di, Li ^a   Mcconnell, Oliver ^a  

^a PFIZER INC   (United States)

Author keywords

Asymmetric enzyme transformations; Automated enzymatic screening; Chiral separations; Enantiomeric excess; Kinetic resolution

Indexed keywords

CARBOXYLIC ACID; ESTER;

ANALYTIC METHOD; ARTICLE; CHIRALITY; ENANTIOMER; ENZYME ANALYSIS; ENZYME MECHANISM; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; MASS SPECTROMETRY; PRIORITY JOURNAL; ULTRAVIOLET RADIATION;

ANIMALS; CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYDROLYSIS; KINETICS; MASS SPECTROMETRY; MODELS, CHEMICAL; REPRODUCIBILITY OF RESULTS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM; SWINE; TECHNOLOGY, PHARMACEUTICAL; TIME FACTORS;

EID: 34748865087     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20432     Document Type: Article

References (15)

1. Aboul-Enein HY, Wainer IW. The impact of stereochemistry on drug development and use. New York: Wiley; 1997.
2. Koeller KM, Wong CH. Enzymes for chemical synthesis. Nature 2001;409:232-240.
3. Klibanov AM. Improving enzymes by using them in organic solvents. Nature 2001;409:241-246.
4. Stinson SC. Chiral drug interactions. Chem Eng News 2001;77:101-120.
5. Beesley TE, Scott RPW. Chiral chromatography. New York: Wiley; 1998.
6. Chiou TW, Chang CC, Lai CT, Tai DF, Kinetic resolution of propranolol by a lipase catalyzed N-acetylation. Bioorg Med Chem Lett 1997;7:433-436.
7. Tang Y, Zukowski J, Armstrong DW. Investigations of enantiomeric separations of fluorenylmethoxycarbonyl amino acids and peptides by HPLC using native cyclodextrins as chiral stationary phases. J Chromatogr 1996;743:261-271.
8. Hattori T, Minato Y, Yao S, Finn MG, Miyano S. Use of racemic derivatizing agent for measurement of enantiomeric excess by circular dichroism spectroscopy. Tetrahedron Lett 2001;42:8015-8018.
9. Wu L, Meurer EC, Cooks RG. Chiral morphing and enantiomeric quantification in mixtures by mass spectrometry. Anal Chem 2004;76:663-671.
10. Guo J, Wu J, Siuzdak G, Finn MG. Measurement of enantiomeric excess by kinetic resolution and mass spectrometry. Angew Chem Int Ed 1999;38:1755-1758.
11. Evans MA, Morken JP. Isotopically chiral probes for in-situ high-throughput asymmetric reaction analysis. J Am Chem Soc 2002;124:9020-9021.
12. Zhu X, Lin B, Jakob A, Wuerthner S, Koppenhoefer B. Separation of drug by capillary electrophoresis, Part 10: permethyl-alpha-cyclodextrin as chiral solvating agent. Electrophoresis 1999;20:1878-1889.
13. Cardillo G, Tolomelli A, Tomasini C. Enzymatic resolution of α-alkyl and β-amino acids using immobilized penicillin G acylase. J Org Chem 1996;61:8651-8654.
14. Reetz MT, Kuhling KM, Wilensek S, Husmann H, Hausig UW, Hermes M. A GC-based method for high-throughput screening of enantioselective catalysts. Catal Today 2001;67:389-396.
15. Di L, McConnell OJ, Kerns EH, Sutherland AG. Rapid, automated screening method for enzymatic transformations using a robotic system and supercritical fluid chromatography. J Chromatogr B 2004;809:231-235.