High-performance liquid chromatographic enantioseparation of (R,S)-fluoxetine using Marfey's reagent and (S)-N-(4-nitrophenoxycarbonyl) phenylalanine methoxyethyl ester as chiral derivatizing reagents along with direct thin-layer chromatographic resolution and isolation of enantiomers using L-tartaric acid as mobile phase additive.
Chiral assay of enantiomers of fluoxetine was achieved in pharmaceutical formulations using direct and indirect methods. L-tartaric acid was used as a mobile phase additive in thin-layer chromatography; the enantiomers were separated and isolated and were used to determine the elution order in HPLC. (R,S)-flouxetine was derivatized with (S)-N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester [(S)-NIFE], Marfey's reagent and 1-fluoro-2,4-dinitrophenyl-L-methionine amide (FDNP-L-Met-NH₂. The diastereomers were separated using RP-HPLC. The effect of flow rate and TFA concentration on resolution was studied. The diastereomers obtained by derivatization with FDNP-L-Met-NH₂ were also separated by RP-TLC.
Bhushan
Ravi
R
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee-247667, India. rbushfcy@iitr.ernet.in
Agarwal
Charu
C
D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D002855:Chromatography, Thin Layer / Q000295:instrumentation / Q000379:methods*; D005473:Fluoxetine / Q000737:chemistry* / Q000302:isolation & purification*; D009574:Nitro Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry
C467080:N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester; D009574:Nitro Compounds; D013644:Tartrates; D005473:Fluoxetine; C029768:tartaric acid