Development of ultrathin chiral separation membranes made of homochiral lipids

이요한,최시영 한국공업화학회 2019 한국공업화학회 연구논문 초록집 Vol.2019 No.1

Different enantiomers result in different effects in various industries, which has required optically pure enantiomers and stimulated the development of new and effective chiral separation methods. In this research, a new technique for the separation of chiral molecules using homochiral lipid membranes is introduced, which is expected to achieve both high permeability and selectivity at the same time. The ultrathin freestanding separation membrane was created by a spontaneous self-assembly of lipid molecules. Then, membrane transport of each enantiomer was measured respectively. Once the chiral-selective transport is confirmed, a racemic compound was provided and the enantiomeric excess after membrane transport was identified via circular dichroism (CD) spectroscopy. Further modification of our lipid bilayer composition is expected to increase the separation efficiency and give information of key factors for this unconventional chiral separation method.

Chiral Drugs의 광학분할을 위한 HPLC Column의 응용

이원재,Lee, Won-Jae 대한약학회 2009 약학회지 Vol.53 No.2

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.

신약개발을 위한 정밀화학기술 Chiral Separation의 효율향상을 위한 Modified Biocatalyst

정찬성 ( Jeong Chan Seong ),이소하 ( Lee So Ha ) 한국공업화학회 2003 공업화학전망 Vol.6 No.4

Engineering Homochiral Metal-Organic Frameworks for Heterogeneous Asymmetric Catalysis and Enantioselective Separation

Liu, Yan,Xuan, Weimin,Cui, Yong WILEY-VCH Verlag 2010 ADVANCED MATERIALS Vol.22 No.37

<P>Owing to the potential applications in technological areas such as gas storage, catalysis, separation, sensing and nonlinear optics, tremendous efforts have been devoted to the development of porous metal-organic frameworks (MOFs) over the past ten years. Homochiral porous MOFs are particularly attractive candidates as heterogeneous asymmetric catalysts and enantioselective adsorbents and separators for production of optically active organic compounds due to the lack of homochiral inorganic porous materials such as zeolites. In this review, we summarize the recent research progress in homochiral MOF materials, including their synthetic strategy, distinctive structural features and latest advances in asymmetric heterogeneous catalysis and enantioselective separation.</P> <B>Graphic Abstract</B> <P>Homochiral porous metal-organic frameworks (MOFs) are particularly attractive candidates as heterogeneous asymmetric catalysts and enantioselective adsorbents and separators for production of optically active organic compounds. This review summarizes the recent research progress in homochiral MOF materials, including their synthetic strategy, distinctive structural features and applications in enantioselective catalysis and separation. <img src='wiley_img_2010/09359648-2010-22-37-ADMA201000197-content.gif' alt='wiley_img_2010/09359648-2010-22-37-ADMA201000197-content'> </P>

Methods for separation of organic and pharmaceutical compounds by different polymer materials

Pravin Ganeshrao Ingole,Neha Pravin Ingole 한국화학공학회 2014 Korean Journal of Chemical Engineering Vol.31 No.12

The discrimination of enantiomers is a challenging task in separation technology, and using a membraneis most promising for separating enantiomers from racemic mixture. The optical resolution of chiral compounds is ofinterest to researchers working in a variety of fields from analytical, organic and medicinal chemistry, to pharmaceu-tics and materials, to process engineering for fabricating pharmaceuticals, agrochemicals, fragrances and foods, and soon. There is considerable demand for separation techniques appropriate for the large-scale resolution of chiral molecules. The separation of chiral compounds using chiral or achiral/non-chiral polymeric membranes with or without chiralselector represents a promising system for future commercial applications. This review focuses on an active field ofchiral separation, membrane-based enantioseparation technique, which has potential for large-scale production of single-enantiomers. Enantiomeric separation by membrane processes has been studied using various configurations of liquidand solid polymer membranes. Selectivity and permeability of liquid-membranes is reasonably good because the rateof diffusion of solute molecules is high in liquids but has inferior durability and stability. Solid polymer membraneshave inferior permeability because diffusion of solute through solids is slow but quite stable and durable; however,commercial application of membrane technology for optical resolution is yet to be realized. Several chiral separationmembranes were prepared from chiral polymers where enantioselectivity was generated from chiral carbons in the mainchain. However, it is rather tricky to generate excellent chiral separation membranes from chiral polymers alone, becauseracemic penetrants mainly encounter the flexible side chains of the membrane polymers.

Chiral separation using chiral crown ethers as chiral selectors in chirotechnology

Suraj Adhikari,이원재 한국약제학회 2018 Journal of Pharmaceutical Investigation Vol.48 No.3

This article reviews the enantiomer separation using two typical chiral crown ethers as chiral selectors in chirotechnology. The coated chiral crown ether type chiral stationary phase (CSP) derived from bis-(1,1′-binaphthyl)- 22-crown-6 and the covalently bonded chiral crown ether type CSP derived from (18-crown-6)-2,3,11,12-tetracarboxylic acid (18-C-6-TA) in the term of their suitability and applicability are discussed and compared in chiral HPLC. It was shown that the covalently bonded type CSP using 18-C-6-TA as a chiral selector has been widely applied for resolving various chiral primary amines in chiral HPLC. Furthermore, this article focuses on the enantiomer separation and their applications using (+)- and/or (−)-18-C-6-TA as chiral selectors for capillary electrophoresis as well as a chiral solvating agent for nuclear magnetic resonance spectroscopy.

Open tubular layer of S-ofloxacin imprinted polymer fabricated in silica capillary for chiral CEC separation

Zaidi, Shabi Abbas,Han, Kyoung Moon,Kim, Sung Soon,Hwang, Dong Guk,Cheong, Won Jo WILEY-VCH Verlag 2009 Journal of Separation Science Vol.32 No.7

<P>An open tubular molecule imprinted polymer (OT-MIP) capillary column has been prepared for chiral separation of ofloxacin enantiomers in CEC. The S-ofloxacin imprinted OT column was fabricated by thermally initiated non-covalent polymerization procedure inside a pretreated and silanized fused silica capillary. The template molecule was incorporated with methacrylic acid (MAA), ethylene glycol dimethacrylate (EDMA) and 4-styrenesulfonic acid (4-SSA) and dissolved in a porogen mixture of ACN/2-propanol (9:1). The separation efficiency of the 4-SSA MIP column was found quite better than that of the MIP column without 4-SSA. It has been demonstrated that our OT-MIP column can separate ofloxacin enantiomers with excellent chiral separation efficiency after tuning the various chromatographic conditions. The optimized chromatographic eluent was 85:15, v/v%, ACN/60 mM sodium acetate at pH 7. The separation efficiency and selectivity of chiral separation of this study were far better than those obtained by previous methods for chiral separation of R- and S-ofloxacin.</P>

Enantiomer Separation of Chiral Amines and Amino Acid Esters on Polysaccharide Phenylcarbamates Derived Chiral Stationary Phases

Suraj Adhikari,Alisha Bhandari,Wonjae Lee 대한약학회 2021 약학회지 Vol.65 No.3

We have developed an efficient chiral HPLC method for enantiomeric resolution of some chiral amines and α- amino acid esters as nitrobenzoxadiazole (NBD) derivatives on amylose and cellulose phenylcarbamates derived chiral stationary phases (CSPs) under simultaneous ultraviolet (UV) and fluorescence (FL) detection. The observed enantioselectivities were affected by the type of the analyte (amines or α-amino acid esters), backbone structure (cellulose or amylose) of the CSP used, and substituents of phenyl moiety on the chiral selector of CSP. Further, for same chiral selectors, coated type CSPs showed better enantiomeric separation than those observed for the covalently bonded type CSPs. In general, for the enantiomeric resolution of chiral amines, Chiralpak IE and Chiralcel OD-H columns showed the highest enantioselectivities. However, for resolution of α-amino acid esters, the performances of Chiralpak IA and Chiralpak AD-H (or Lux Amylose-1) columns were superior to those of other CSPs used. In general, the degrees of enantioselectivity for α-amino acid ethyl esters are greater than those for chiral amines. The developed analytical method was applied to determine the enantiomeric purity of two commercially available chiral amine and α-amino acid ester; the enantiomeric impurities were observed to be 0.35 and 0.05% for (S)-α-methylbenzylamine and (S)-leucine ethyl ester, respectively. The validation data obtained from intra- and inter-day accuracy assays for (S)-3,3-dimethyl-2-butylamine and (S)-leucine ethyl ester were 99.92-101.46 and 100.61-101.78%; and 100.05-102.12 and 101.25-102.73%, respectively; the intra- and interday precision assays in terms of relative standard deviation (% RSD) were found to be 0.96-1.57 and 0.81- 1.91%; and 0.24-1.01% and 0.65-1.35%, respectively. Owing to the high accuracy and precision results, the developed analytical method can prove to be useful for the enantiomeric separation of various chiral amines and amino acid esters as NBD derivatives using polysaccharide derived CSPs.

CHIRAL CARBON NANOTUBES AND CARBON NANOTUBE CHIRAL COMPOSITES:PREPARATION AND APPLICATIONS

XIAOQING CHEN,XIAO-YUN LIAO,JIN-GANG YU,FEI-PENG JIAO,XINYU JIANG 성균관대학교(자연과학캠퍼스) 성균나노과학기술원 2013 NANO Vol.8 No.4

A review of preparation of chiral carbon nanotubes (CNTs) and carbon nanotube chiral composites is presented. Novel chiral separation science and technology based on CNTs is analyzed and discussed, with the emphasis in two topics. The first topic concerns the possibility of application of chiral CNTs in resolution and chiral sensing. The second topic centers on the subject of enantioseparation based on CNT chiral composites. Despite the crucial functionalization of CNTs using chiral selectors, better resolution could also be achieved by using a mixture of CNTs and optical pure substances as chiral selectors. Due to their ability of improving the degree of enantioseparation, CNTs could find their potential applications in the resolution in the future.

Liquid Chromatographic Chiral Separations by Crown Ether-Based Chiral Stationary Phases

Choi, Hee Jung,Hyun, Myung Ho Taylor Francis 2007 Journal of liquid chromatography & related technol Vol.30 No.5

<P> Liquid chromatographic chiral stationary phases (CSPs) based on chiral crown ethers have been successfully utilized in the separation of the enantiomers of various racemic compounds containing a primary amino group. Especially, CSPs based on chiral crown ethers incorporating chiral binaphthyl unit or tartaric acid unit have been most successful. In this review, the development of CSPs based on chiral crown ethers incorporating a chiral binaphthyl unit or a tartaric acid unit, their applications to the resolution of various primary and non-primary amino compounds with the variation of the type and the content of organic, acidic, and inorganic modifiers in an aqueous mobile phase or with a non-aqueous mobile phase and the efforts to improve the chiral recognition efficiency or the stability of the CSPs have been discussed.</P>