Direct enantioselective HPLC monitoring of lipase-catalyzed kinetic resolution of tiaprofenic acid in nonstandard HPLC organic solvents.
The first straightforward lipase-catalyzed enantioselective access to enantiomerically enriched tiaprofenic acid as a versatile method in chiral separation of racemates is demonstrated. The latter was directly monitored by enantioselective HPLC using a 3,5-dimethylphenylcarbamate derivative of cellulose-based chiral stationary phase namely Chiralpak IB (the immobilized version of Chiralcel OD). Non-standard HPLC organic solvents were used as diluent to dissolve the "difficult to dissolve" enzyme substrate (the acid) and as eluent for the simultaneous enantioselective HPLC baseline separation of both substrate and product in one run without any further derivatization. The existence of a non-standard HPLC organic solvent (e.g., methyl tert-butyl ether) in the mobile phase composition is mandatory to accomplish the simultaneous enantioselective HPLC baseline separation of both substrate and product.
Ghanem
Ashraf
A
Biomedicinal Chemistry Unit, Biological and Medical Research Department, King Faisal Specialist Hospital and Research Centre, Riyadh, Saudi Arabia. ghanem@kfshrc.edu.sa
Aboul-Enein
Mohammed Nabil
MN
El-Azzouny
Aida
A
El-Behairy
Mohammed F
MF
Al-Humaidi
Ebtessam
E
Alaidan
Alwaleed A
AA
Amin
Kamilia
K
Al-Ahdal
Mohammed N
MN
D002384:Catalysis; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D009930:Organic Chemicals / Q000737:chemistry*; D011422:Propionates / Q000302:isolation & purification / Q000378:metabolism*; D012997:Solvents / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D009930:Organic Chemicals; D011422:Propionates; D012997:Solvents; C021270:tiaprofenic acid; D008049:Lipase