Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Special issue | Vol 97, No. 1, 2018, pp.273-282
Published online, 26th February, 2018
DOI: 10.3987/COM-18-S(T)17
Derivatization of Secondary Aliphatic Alcohols to Picolinates – A New Option for HPLC Analysis with Chiral Stationary Phase

Keita Nishimura, Shuhei Tanabe, Riku Shinohara, and Yuichi Kobayashi*

*Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, Box B52, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan


Derivatization of secondary alcohols (R1R2CHOH) to benzoates has frequently employed to determine enantiomer ratios using HPLC with chiral stationary phase (CSP). However, a small difference in substituents (R1, R2) often results in insufficient separation. To find an alternative derivatization that detects such a small difference, picolinates (2-pyridyl-CO2CHR1R2) possessing Me/Et, Me/vinyl, Me/acetylenic, Et/n-Pr, and n-Pr/allyl substituents were prepared and separation efficiency was compared with that of benzoates (PhCO2CHR1R2). Eight commercially available CSPs containing carbamates or benzoates of cellulose and amylose were examined to find that retention factors (k'1 and k'2) and resolution (Rs) of picolinates were greater than those of the corresponding benzoates and that good to excellent Rs values (≥1.25) were recorded over a wide range of CSPs.