• Title/Summary/Keyword: Enantiomer separation

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Indirect chiral separation of $\alpha$-arylmethylpropionic acids by liquid chromatography

  • Min, Chung-Sik;Jang, Seung-Jae;Choi, Bo-Kyung;Kim, Young-Lim;Jung, Hae-Yun;Bak, Kyung-Min;Lee, Kyung-Hee;Jo, Keang-In;Gu, You-Ni
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.215.1-215.1
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    • 2003
  • A various ${\alpha}$-arylmethylpropionic acids(profen) have been widely used as non-steroidal anti-inflammatory drugs for the relief of acute and chronic rheumatoid arthritis and osteoarthritis, as well as for other connective tissue disorders and pains. Example is fenoprofen, ibuprofen, ketoprofen, and naproxen. All are chiral and, except for naproxen and ibuprofen, are marketed in racemic form. Enantioseparations of profens have been of considerable interest becaus their anti-inflammatory and analgesic effects have been attirbuted almost exclusively to their (S)-enantiomer. (omitted)

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Analysis of Volatile Compounds and Enantiomeric Separation of Chiral Compounds of Dried Sancho (Zanthoxylum schinifolium Siebold & Zucc)

  • Seo, Hye-Young;Shim, Sung-Lye;Ryu, Keun-Young;Jung, Min-Seok;Hwang, In-Min;Shin, Dong-Bin;Kwon, Joong-Ho;Schreier, Peter;Kim, Kyong-Su
    • Food Science and Biotechnology
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    • v.18 no.1
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    • pp.18-24
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    • 2009
  • The volatile compounds of dried sancho (Zanthoxylum schinifolium), an aromatic plant were extracted by simultaneous distillation and extraction (SDE) method and identified by gas chromatograph-mass spectrometry (GC-MS). Selected chiral constituents of sancho oil were characterized by enantiodifferentiation using multidimensional gas chromatograph (MDGC)-MS. A total of 57 compounds were identified and quantified, and the major compounds were identified estragole, nonanoic acid, octanoic acid, $\beta$-phellandrenene, and limonene. Among them, estragol (63.9%) was found as the predominantly abundant component of sancho. $\alpha$-pinene and nerolidol, and $\beta$-pinene and linalool were determined to be enantiomerically pure (100%) for their (S)-form and (R)-form, respectively. The enantiomeric composition of limonene in sancho revealed 83.9% purity for the (S)-enantiomer, whereas (E)- and (Z)-rose oxides showed mixtures of both enantiomers. The enantiomeric excess (%) for citronellal was 22.6% with the (R)-enantiomer as major enantiomer. The enantiomeric composition of these compounds can be used as parameter for authenticity control of sancho.

Monitoring of the Optical Purity for Levothyroxine Sodium in Pharmaceuticals Using Crown Ether Derived Chiral Columns (크라운 에테르에서 유도된 키랄 컬럼을 사용한 레보티록신 나트륨 의약품의 광학순도 모니터링)

  • Jeon, So-Hee;Lee, Won-Jae
    • KSBB Journal
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    • v.25 no.5
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    • pp.449-452
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    • 2010
  • L-Thyroxine possessing a chiral center, the naturally occurring thyroid hormone has been used for the treatment of thyroid dysfunctions and marketed as levothyroxine (L-thyroxine) sodium salt. In this study, after extraction of levothyroxine tablet as a pre-treatment process, direct enantiomer separation of thyroxine on crown ether derived chiral columns for determination of optical purity was performed using reversed mobile phase with acid additive. The chromatographic method developed in this study was applied in the determination of optical purity of several current domestic and foreign commercialized levothyroxine tablets. Optical purity values of these commercialized L-thyroxine sodium tablets except one were higher than 99 percents.

Enantioselective electrophoretic behavior of lipoic acid in single and dual cyclodextrin systems

  • Le, Thi-Anh-Tuyet;Nguyen, Bao-Tan;Phan, Thanh Dung;Kang, Jong-Seong;Kim, Kyeong Ho
    • Analytical Science and Technology
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    • v.34 no.4
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    • pp.143-152
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    • 2021
  • Capillary electrophoresis (CE) is an effective technique to study chiral recognition because it offers flexibility in adjusting vital factors. Currently, various available cyclodextrins (CDs) can be employed for the chiral separation of numerous analytes. Herein, we investigate the enantioseparation behavior of lipoic acid enantiomers in various types of single and dual CD systems through CE. Additionally, several impacted CE parameters were optimized through the systematic investigation based on the design of experiment (DoE) concept for a single system comprising a heptakis (2,3,6-tri-O-methyl)-β-CD and a dual system containing the combination of the single CD with a sulfated-β-CD. Consequently, absolute enantioresolution was obtained within 15 min on a common standard bare fused-silica capillary (64.5/56 cm in total/effective length, 50/365 ㎛ inner/outer diameter), maintained at 15 ℃ and at an applied voltage of 24 kV. The optimal background electrolyte consisted of 6 mM heptakis (2,3,6-tri-O-methyl)-β-CD dissolved in the solution of 58 mM borate buffer at pH 10. Furthermore, the results of apparent binding constant experiments indicated that the S-enantiomer-heptakis (2,3,6-tri-O-methyl)-β-CD complex exhibited a stronger affinity than its R-enantiomer counterpart. The obtained electrophoretic mobility values could be utilized to interpret the resolution achieved at various CD concentrations and the mobility behavior of the complexes elucidated the migration order of the enantiomers in an electropherogram.

Coupled Column Chromatography in Chiral Separation of Salmeterol

  • Kim, Kyeong-Ho;Yun, Hyeong-Won;Kim, Hyun-Ju;Park, Hyun-Ji;Choi, Pok-Wha
    • Archives of Pharmacal Research
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    • v.21 no.2
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    • pp.212-216
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    • 1998
  • A coupled achiral-chiral high-performance liquid chromatographic system has been developed for the determination of the enantiomers of salmeterol, S-(+)-salmeterol and R-(-)-salmeterol in urine. THe salmeterol was separated from the interfering components in urine and quantified on the silica column, and the enantiomeric composition was determined on a Sumichiral OA-4700 chiral stationary phase. The two columns were connected by a switching valve equipped with a silica precolumn. The two columns wer connected by a switching valve equipped with a silica precolumn. The precolumn was used to concentrate the salmeterol in the eluent from the achiral column before backflushing onto the chiral phase. The coupled system was validated.

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Recemization of L-Lysine for Pharmaceutical Synthesis and its Chiral Separation by GC-MS Spectroscopy

  • Cheong, Jae-Yeon;Choi, Su-Hang;Nam, Tae-Woo;Shin, Jae-Young;Kim, Su-Woong;Jung, Won-Tae
    • Archives of Pharmacal Research
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    • v.18 no.2
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    • pp.69-74
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    • 1995
  • In order to improve physico-chemical properties and to enhance stability of drugs, amino acid salt has been widely adoptd in pharmaceutical synthesis. Acetylsalicylic acid lysinate is one of the widely used analgesics and it is a good example of t5his synthesis. In the case of bacetylsalicylic acid lysinate synthesis, racemization of natrually occurred lysine is esential because the racemic lysine salt of the drug shows better yield, crystallinity and dryness than that of the L-lysine salt. To esatablish a simple, practical and economical process for L-lysine racemization, L-lysine treatments with phosphoric acid and with acetic acid were compared and the optimum conditions for its process and derivatization were investigated by chiral separation methods using GC_MS spectroscopy.

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