Journal
CHROMATOGRAPHIA
Volume 81, Issue 12, Pages 1613-1621Publisher
SPRINGER HEIDELBERG
DOI: 10.1007/s10337-018-3546-9
Keywords
Chiral liquid chromatography; Polar organic mode; Thermodynamic study; Van't Hoff analysis; U-shaped retention curve; Otezla
Funding
- New National Excellence Program of The Ministry of Human Capacities [UNKP-17-4]
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Enantioseparation of an anti-psoriatic agent, apremilast(APR), was performed by HPLC using polysaccharide-type chiral stationary phases in polar organic mode for the first time. The separation capability of six different chiral columns (Chiralpak AD, Chiralpak IA, Chiralpak AS, Lux Amylose-2, Chiralcel OD and Chiralcel OJ-H) was investigated using neat MeOH and ACN. During the preliminary experiments the best results were obtained on Chiralpak IA column with ACN (R-s=5.4). The effects of binary mobile phases on the resolutions and retention factors were also investigated containing different percentages of MeOH:ACN. U-shaped retention pattern was obtained when plotting the retention factors of the APR enantiomers versus the MeOH content of the binary mobile phases on Chiralpak IA column. For further method optimizations an L25 orthogonal array table was employed altering the concentration of MeOH in ACN, column temperature, and flow rate. The best result was achieved on Chiralpak IA column with 80/20 (v/v%) MeOH/ACN with 0.7mL min(-1) flow rate at 25 degrees C (R-s=5.4, t(2)=7.45min). Thermodynamic analysis revealed an enthalpy-driven enantioseparation. The developed HPLC method was validated according to the ICH guideline Q2(R1) and proved to be reliable, linear, precise and accurate for the determination of 0.1% R-enantiomer as chiral impurity in S-APR as well as quantification of the S-enantiomer. [GRAPHICS] .
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