• KSBB Journal
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• 제15권6호
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• pp.541-547
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• 2000

Simulated moving bed (SMB) chromatography has been investigated in order to separate chiral compounds for pharmaceutical use. SMB utilizes the principle of true moving bed (TMB) chromatography, and has the advantages of low solvent usage, flexible configuration of columns and hardwares, and high productivity of the chiral compounds over the TMB. Large scale separation of xylene isomers and saccharides has been conducted since 1960s. However, the application of SMB in the fine chemical industries is still in the infant stage. The study of SMB for the chiral compounds production was initiated in the mid 1990s and further researches are actively undergoing. This review summarizes the principle of SMB as well as the chemistry of chiral stationary phase and chiral compounds.

• KSBB Journal
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• 제20권3호
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• pp.177-182
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• 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.

• 통합자연과학논문집
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• 제9권1호
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• pp.28-34
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• 2016

A number of chiral selectors have been developed and applied for enantiomer separation of a variety of chiral compounds. Among these chiral selectors are chiral crown ethers, a class of synthetic host polyether molecules that bind protonated chiral primary amines with high selectivity and affinity. In this paper, two important chiral crown ethers as chiral selectors of bis-(1,1'-binaphthyl)-22-crown-6 and (18-crown-6)-2,3,11,12-tetracarboxylic acid (18-C-6-TA) are focused. They have been widely used to resolve the enantiomers of chiral compounds containing a primary amino moiety using chiral stationary phases (CSPs) or chiral selectors by high-performance liquid chromatography (HPLC), capillary electrophoresis (CE) and so on in chirotechnology. Also, it was described that the commercially available covalent type HPLC CSPs derived from (+)- and (-)-18-C-6-TA have been developed and successfully applied for the resolution of various primary amino compounds including amino acids.

• 약학회지
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• 제53권2호
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• pp.60-68
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• 2009

In terms of chiral issue, two enantiomers of chiral drugs often differ significantly in their pharmacological, toxicological and pharmacokinetic profile. Chiral switches of racemic drugs have been redeveloped as single enantiomers. Several chiral resolution techniques in chirotechnology are introduced and the most used chiral HPLC chromatographic method among several chiral analysis techniques is described with its several advantages. Several types of chiral HPLC columns derived from their chiral selectors are discussed with their property and applications for enantiomer separation.

• Archives of Pharmacal Research
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• 제24권5호
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• pp.402-406
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• 2001

Gas chromatographic method was investigated for the chiral separation of several $\beta$-blockeros(atenolol, betaxolol, bisoprolol, metoprolol and pindolol) using (-)-$\alpa$-methoxy-$\alpa$-(trifluoromethyl)phenylacetyl chloride as a chiral derivatizing agent for amino group. Prior to N-acylation, hydroxyl group was converted into O-silyl ethers by react with N-methyl-H-(taimethylsilyl)trifluoroacetamide. The reaction was selective and rapid and the diasteromeric derivatives were well separated by capillary gas chromatography. (R)-isomers were eluted faster than (S)-isomers when (-)-$\alpa$-methoxy-$\alpa$-(trifluoromethyl)phenylacetyl chloride was used as the chiral derivatizing agent. But in the opposite sequence when (+)-$\alpa$-methoxy-$\alpa$-(trifluoromethyl)phenylacetyl chloride was used. No racemization was found during the reaction.

• KSBB Journal
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• 제27권4호
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• pp.199-206
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• 2012

Chiral crown ethers are synthetic macrocyclic polyethers that bind protonated chiral primary amines with high selectivity and affinity. They have been widely used to separate or distinguish the enantiomers of chiral compounds containing a primary amino moiety by high-performance liquid chromatography, capillary electrophoresis, and NMR spectroscopy. In this paper, two important chiral crown ethers including chiral binaphthyl unit and (18-crown-6)-2,3,11,12-tetracarboxylic acid as chiral selectors are focused. And several chiral resolution techniques and their applications in chirotechnology using these chiral crown ethers with related chiral recognition mechanism studies are reviewed. Especially, it was shown that the commercially available HPLC columns based on (18-crown-6)-2,3,11,12-tetracarboxylic acid have been developed and successfully applied for the resolution of various primary amino compounds including amino acids.

• Bulletin of the Korean Chemical Society
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• 제34권9호
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• pp.2623-2628
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• 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.

• KSBB Journal
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• 제19권4호
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• pp.263-268
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• 2004

최근 생체 내에서 다른 약리활성을 보이는 키랄물질의 고순도 제조에 관심이 증가되고 있다. 현재 널리 사용되고 있는 것은 키랄고정상을 이용한 기존 분리방법에 비해서, 제조 후 안정성과 환경적인 측면을 고려한 초임계유체를 이용한 분리방을 시도하였다. 본 연구에서는 키랄물질인 ibuprofen의 최적의 분리 조건을 구하기 위해서 온도와 압력, 첨가되는 IPA의 양에 따른 체류인자와 분리도의 영향을 고찰하였다. 온도가 감소하고 압력이 증가할수록 체류인자는 감소하였다. IPA의 양에 따라 더 큰 영향을 받아서 IPA의 양이 많을수록 분리도는 감소하는 경향을 보였다. 실험으로부터 정한 최적의 분리조건은 130 bar, 311.15 K, 4% IPA (vol.)일 때이었다. 동일한 주입량에서 액체 크로마토그래피에서는 비선형의 용출곡선을 보였지만, 초임계유체 크로마토그래피에서는 선형의 용출곡선을 얻었다.

• Biotechnology and Bioprocess Engineering:BBE
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• 제5권1호
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• pp.17-22
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• 2000

The separation of tryptophan enantiomers was carried out with medium-pressure liquid chromatography using BSA (bovine serum albumin)-bonded silica as a chiral stationary phase. The influence of various experimental factors such as pH and ionic strength of mobile phase, separation temperature, and the presence of organic additives on the resolution was studied. In order to expand this system to preparative scale, the loadability of sample and the stability of stationary phase for repeated use were also examined. The separation of tryptophan enantiomers was successful with this system. The data indicated that a higher separation factor (a) was obtained at a higher pH and lower temperature and ionic strength in mobile phase. Addition of organic additives (acetonitrile and 2-propanol) in mobile phase contributed to reduce the retention time of L-tryptophan. About $30\%$ of the separation factor was reduced after 80 days of repeated use.

• Bulletin of the Korean Chemical Society
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• 제25권9호
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• pp.1336-1340
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• 2004

The same kind of chiral stationary phase with a commercialized chiral column was used to make preparative chiral columns and was applied to resolve racemic N-acetyl-1-naphthylethylamide (3) by preparative liquid chromatography. An improved chromatographic condition to resolve racemic 3 on the CSP was examined by changing flow rate and kind of the mobile phase and the sample injection volume. The optimized separation conditions were applied to resolve racemic 1,1'-Binaphthyl-2,2'-diamine(4).