• 제목/요약/키워드: chiral separation

검색결과 195건 처리시간 0.027초

Preparation of Bonded Cellulose Tris(3,5-dimethylphenylcarbamate) Chiral Stationary Phases by Using Three Bifunctional Reagents

  • Zhang, Yi Jun;Huang, Mingxian;Zhang, Yuping;Ryoo, Jae Jeong
    • Bulletin of the Korean Chemical Society
    • /
    • 제34권9호
    • /
    • pp.2623-2628
    • /
    • 2013
  • Three di-acyl chlolide reagents, adipoyl chloride, terephthaloyl chloride and isophthaloyl chloride, were used as spacer reagents to prepare bonded type of three cellulose (3,5-dimethylphenyl)carbamate (CDMPC) chiral stationary phases (CSPs). The CDMPC CSPs were prepared using these three acid chlorides as spacer agents at the 6-position of the primary hydroxyl group on the glucose unit of cellulose regioselectively. The chiral recognition ability of the prepared CSPs for five racemates was evaluated by normal-phase high-performance liquid chromatography (HPLC) with the following mobile phases: hexane/isopropanol (IPA), hexane/IPA/tetrahydrofuran (THF) and hexane/IPA/chloroform. The result showed that these prepared CSPs can be used in THF and chloroform solutions and the chiral recognition abilities of the CSPs were improved depending on the eluents and chiral samples.

Chiral Purity Test of Metoprolol Enantiomer After Derivatization with (-)-Menthyl Chloroformate by Reversed-Phase High Performance Liquid Chromatography

  • Kim, Kyeong-Ho;Choi, Pok-Wha;Hong, Seon-Pyo;Kim, Hyun-Ju
    • Archives of Pharmacal Research
    • /
    • 제22권6호
    • /
    • pp.614-618
    • /
    • 1999
  • A reversed-phase high-performace liquid chromatographic method was developed to determine the optical purity of metoprolol enantiomers. The enantiomers were converted to diastereomeric derivatives using (-)-menthyl chloroformate reagent. Separation of the enantiomers as diastereomers was achieved by reversed-phase HPLC within 30 min using Inertsil C8 column. This method allowed determination of 0.05% of either enantiomer in the presence of its stereoisomer and method validation showed adequate linearity over the required range. Owing to the reaction condition during the derivatization with (-)-menthyl chloroformate, the possibility of racemization had to be established. Different ratios of (S)-(-)-metoprolol and (R)-(+)-metoprolol were prepared. Enantiomeric separation of these mixtures took place on a chiralcel OD column or, after derivatization with (-)-menthyl chloroformate, on a C8 column. The results form the these two independent separation systems were compared with trace racemization and were in very good agreement. No racemization was found during the experiment.

  • PDF

PREPARATION AND CHARACTERIZATION OF THE CHIRAL STATIONARY PHASE BASED ON THE CHITOSAN

  • Son, Seung-Hee;Jonggeon Jegal;Lee, Kew-Ho
    • 한국막학회:학술대회논문집
    • /
    • 한국막학회 2003년도 The 4th Korea-Italy Workshop
    • /
    • pp.103-105
    • /
    • 2003
  • A chiral stationary phase (CSP) was synthesized by the modification of the chitosan using N-nicotinoyl phenylalanine and 3, 5-dimethylphenylisocyanate . The CSP based on the chitosan was then characterized in terms of their chemical structure and physical properties. To test its performance as a CSP, the silica powder with 5 ${\mu}{\textrm}{m}$ of diameter were coated with the CSP to pack a column for High Performance Liquid Chromatograph (HPLC). Using the packed column, several racemates were tried to separate under various separation conditions with different compositions of eluents.

  • PDF

Capillary Electrophoresis에 의한 carvedilol 및 그 대사체의 거울상이성질체 분리 (Separation of racemic enantiomer carvedilol and its metabolites using capillary electrophoresis)

  • 조천호;구소현;명승운
    • 분석과학
    • /
    • 제19권4호
    • /
    • pp.275-279
    • /
    • 2006
  • A capillary electrophoresis method for the separation of carvedilol and its metabolites enantiomers using cyclodextrins as the chiral selectors was developed. The effect of several types of cyclodextrins, concentration and capillary temperature for enantiomer resolution were investigated. Best results were obtained by 15 mM carboxymethyl-${\beta}$-cyclodextrin in the run buffer. Also the effect of capillary temperature on efficiency was assessed. The optimized method was applied for separation of chiral carvedilol and its three metabolites.

SMB 크로마토그래피에서 키랄정지상 [Chiral Stationary Phase, CSP]의 사용 (CSP [Chiral Stationary phase] for SMB Chromatography)

  • 김병립;김인호
    • KSBB Journal
    • /
    • 제20권3호
    • /
    • pp.177-182
    • /
    • 2005
  • Simulated moving bed (SMB) chromatography was used in the petrochemical industry in the 1960s and its use has been widened to separate chiral compounds in the 1990s. Chiral stationary phase (CSP) is the key component in SMB for the separation of the chiral compounds. CSP has been developed for the analytical use in HPLC, however, its development successfully adapted for the preparative use in SMB chromatography. This review covers the present state-art technology of CSP for SMB chromatography in terms of selectivity, stability, and capacity.

아미노산 Phenylthiohydantoin 유도체를 키랄 고정상으로 한 GC에 의한 아미노산 광학 이성질체의 상호분리 (Separation of Amino Acid Enantiomers by Gas Chromatogaphy on Phenylthiohydantoin Derivatives as Chiral Stationary Phases)

  • 박만기;양정선;고창범;이미영
    • 약학회지
    • /
    • 제32권3호
    • /
    • pp.170-176
    • /
    • 1988
  • The resolution of five amino acids derivatives by gas chromatography on phenylthiohydantoin derivatives as chiral stastionary phase was investigated. (S)-5-isopropyl, isobutyl, (sec)-butyl and benzoyl derivatives of $N^3-phenyl-2-thiohydantoin$ were synthesized from L-valine, L-leucine, L-isoleucine and L-phenylalanine, respectively. The phases were employed at several column temperatures ($140^{\circ}C{\sim}210^{\circ}C$). The separation factors were compared with each stationary phase with varying R groups. The possible mechanism of chiral recognition was investigated by NMR technique.

  • PDF

선택적 분리를 위한 분자 각인 고분자의 설계 및 응용 (Design and Applications of Molecularly Imprinted Polymers for Selective Separations)

  • 정수환;오창엽;서정일;박중곤
    • KSBB Journal
    • /
    • 제16권2호
    • /
    • pp.115-122
    • /
    • 2001
  • Molecular imprinting has now been established as a technique which allows the creation of tailor-made binding sites for many classes of compounds. MIPs were prepared by covalent and non-covalent chemical bonding systems, by interactions between functional monomer and template. The shape of MIP is divided to particle and membrane. MIP membranes can be prepared by surface imprinting, in-situ polymerization, wet phase inversion and the dry phase inversion method. MIPs have been mainly used for analytical separation and biosensor systems to separate and detect chiral compounds and materials with similar structures. However the application of MIP by the chemical industries is still in its infancy stages. This review summarizes the preparative characteristics and applications of MIP with respect to chiral separations and biosensors.

  • PDF

Optical Resolution of Dansyl Amino Acids with Addition of Benzyl-L-Hydroxyproline Copper(II) Chelate by High Performance Liquid Chromatography

  • Sun Haing Lee;Tae Sub Oh;Sang Hyun Bak
    • Bulletin of the Korean Chemical Society
    • /
    • 제10권6호
    • /
    • pp.491-495
    • /
    • 1989
  • Resolution of enantiomers of DNS-amino acids has been achieved by a reversed phase liquid chromatography with an addition of a copper(Ⅱ) complex of N-benzyl-L-hydroxyproline to the mobile phase. N-Benzyl-L-hydroxyproline was prepared and used as a chiral ligand of copper(Ⅱ) chelate for the optical resolution. The pH and the concentration of copper(Ⅱ) chelate, organic solvent, and buffer agent in the mobile phase all affect the optical resolutions of dansyl amino acids. The elution orders between D and L-DNS-amino acids were different depending on the structure of the side chain of the amino acids. The retention mechanism for the chiral separation of the dansyl amino acids can be illustrated by the equilibrium of ligand exchange and by hydrophobic interaction with $C_{18}$ stationary phase. The chiral separation can be illustrated with cis and trans effect of the ligand exchange reaction.