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发泄壶Preparation of Polysaccharide-coating Type Chiral Stationary Phases
Since 1980s, chiral high-performance liquid chromatography(HPLC) for separating the enantiomers of racemates has attracted increasing attention (Petersen 2015, Lorenz, Seidel‐Morgenstern 2014, Martens, Bhushan 2014, Shen, Okamoto 2015, Kong, Zhang et al. 2015, Kuang, Ma et al. 2014, Zhang, Zhang et al. 2014). This technique is usually employed to determine enantiomer contents, or to prepare pure enantiomers (Gallinella, Ferretti et al. 2016, Woods, Patel et al. 2014, Zhang, Gil et al. 2015). Chiral stationary phases(CSPs) play an essential role for the enantioseparation by HPLC (Lorenz, Seidel‐Morgenstern 2014, Martens, Bhushan 2014). In this field, the major works are concerning the development of various types of CSPs, which are desired to separate the enantiomers of a wide range of chiral compounds (Guntari, Nam et al. 2014, Kreituss, Bode 2016, Płotka, Biziuk et al. 2014, Poiger, Müller et al. 2015, Suliman, Elbashir et al. 2015, Suzuki, Han et al. 2015). Generally the well-known CSPs are prepared by coating polysaccharide derivatives on solid supports(mostly 3-aminopropyl silica gel), or by covalently immobilizing low-molecular-weight chiral molecules, synthetic chiral polymers,
or polysaccharide derivatives on functionalized silica gel (Chen, Duan et al. 2014, Guesdon, Avrameas 2014, Junter, Thébault et al. 2016, Mohan, Rathner et al. 2015). From the point of practicable application view, the methods to prepare CSPs by coating polysaccharide derivatives on supports are more preferable, because polysaccharides, such as cellulose, amylose and chitosan, etc. are readily available (Lorenz, Seidel‐Morgenstern 2014, Kuang, Ma 2014, Chen, Duan 2014).
Moreover, the CSPs can be easily prepared in bulk. Meanwhile polysaccharide type CSPs possess higher loading for enantiomers than other type CSPs (Shen, Ikai et al. 2014). Accordingly, the chiral columns, which are packed with the CSPs derived from polysaccharide derivatives, are applied worldwide in pharmaceutical industry and in research (Płotka, Biziuk 2014). Okamoto et al. have published many works in this area, and recently they still developed various methods to immobilize polysaccharide derivatives on silica gel in order to improve the CSPs stability (Shen, Okamoto 2016, Zhang, Ma et al. 2015, Zhang, Wang et al. 2015). Among polysaccharides, cellulose was mostly employed to prepare CSPs. In early stage, Okamoto and coworkers prepared cell
ulose tribenzoate and its derivatives with different substituents on the phenyl groups. Afterwards, the columns packed with the CSPs that were prepared by coating cellulose tribenzoate and tris(4-methylbenzoate) on silica gel were commercialized as CHIRALCEL OB and CHIRALCEL OJ (Hu, Huang et al. 2016, Li, Jiang et al. 2016). However, they found that cellulose tris(3,5-dimethylbenzoate) was insoluble in common organic solvents (Okada, Yamamoto et al. 2016). Therefore, it could not be dissolved and coated on the silica gel. Methyl is an electron-donating group, and 3,5-dimethylphenyl is a π-base, which tends to interact with π-acid of chiral compounds(Tan, Fan et al. 2014). In addition, appropriate steric hindrance is necessary for chiral recognition (Mu, Wang et al. 2015, Wang, Chai et al. 2014, Wencel-DelordColobert 2015, Wencel-Delord, Panossian et al. 2015, Yu, Pu 2015). 3,5-Dimethylbenzoyl can appropriately enlarge the steric hindrance for the interaction between the chiral selector and analytes (Peluso, Mamane et al. 2014, Sanganyado, Lu et al. 2014, Zhang, Holder et al. 2014, Zhou, Tang et al. 2015). This view is evidenced by cellulose tris(3,5-dimethylphenylcarbamate), which has been commercialized and became a widely applied chiral selector (Kharaishvili, Jibuti et al. 201
6). Thus, cellulose tris(3,5-dimethylbenzoate) may be a satisfactory chiral selector for enantioseparation (Fanali, Fanali et al. 2016, Gegenava, Chankvetadze et al. 2014, KhaterWest 2014, Liu, Zhang et al. 2014, Wang, Xi et al. 2017, Weng, Bao et al. 2015). The difficulties in coating cellulose tris(3,5-dimethylbenzoate) on silica gel addressed our investigations to alternative procedures, i.e. a polysaccharide was矫姿带 coated on silica gel, and then derivatized (Gegenava, Chankvetadze 2014, Wang, Xi 2017, Weng, Bao 2015).
The silanols on silica gel were end-capped to afford a polysaccharide type CSP (Daghir-Wojtkowiak, Studzińska et al. 2014). As a typical model, cellulose was dissolved in a solution of LiCl in N,N-dimethylacetamide (DMAc), and was then coated on silica gel (Zhang, Liu et al. 2014, Ono, Ishida et al. 2015). The coating cellulose was modified with 3,5-dimethylbenzoyl chloride, followed by end-capping the silanols on the silica gel with various groups to afford new CSPs (Ha, Han et al. 2014). The enantioseparation ability of these CSPs was preliminarily evaluated (AhnHyun 2015). The enantioseparation properties of the different CSPs were compared (Shimomura, Ikai et al. 2014).
References
Lorenz H., and Seidel‐Morgenstern A. "Processes to separate enantiomers." Angew Chem Int Ed 1区 (11.709), 2014, 53(5): 1218-50. (Times Cited: 104)
Martens J., and Bhushan R. "Purification of enantiomeric mixtures in enantioselective synthesis: overlooked errors and scientific basis of separation in achiral environment." Helvetica Chimica Acta 4区 (1.087), 2014, 97(2): 161-87. (Times Cited: 22)
Shen J., and Okamoto Y. "Efficient separation of enantiomers using stereoregular chiral polymers." Chem Rev 1区 (37.369), 2015, 116(3): 1094-138. (Times Cited: 45)
Kong J., Zhang M., Duan A. H., Zhang J. H., Yang R., and Yuan L. M. "Homochiral metal–organic framework used as a stationary phase for high‐performance liquid chromatography." J Sep Sci 3区 (2.741), 兑换券制作2015, 38(4): 556-61. (Times Cited: 13)
Kuang X., Ma Y., Su H., Zhang J., Dong Y.B., and Tang B. "High-performance liquid chromatographic enantioseparation of racemic drugs based on homochiral metal–organic framework." Anal Chem 1区 (5.886), 2014, 86(2): 1277-81. (Times Cited: 51)
Zhang M., Zhang J. H., Zhang Y., Wang B. J., Xie S. M., and Yuan L. M. "Chromatographic study on the high performance separation ability of a homochiral [Cu2(d-Cam)2(4,4‘-bpy)]η based-column by using racemates and positional isomers as test probes." J Chromatogr A 2区 (3.926), 2014, 1325: 163-70. (Times Cited: 25)
Gallinella B., Ferretti R., Zanitti L., Sestili I., Mosca A., and Cirilli R. "Comparison of reversed-phase enantioselective HPLC methods for determining the enantiomeric purity of (S)-omeprazole in the presence of its related substances." J Pharm Anal 3区 (2.641), 2016, 6(2): 132-6. (Times Cited: 0)化石工艺品
Woods R. M., Patel D. C., Lim Y., Breitbach Z. S., Gao H., Keene C., Li G., Kürti L., and Armstrong D. W. "Enantiomeric separation of biaryl atropisomers using cyclofructan based chiral stationary phases." J Chromatogr A 2区 (3.926), 2014, 1357: 172-81. (Times Cited: 27)
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