武漢工程大學研究生試卷本

1、武漢工程大學（碩士）研究生試卷（第 頁）武 漢 工 程 大 學（碩士）研究生試卷本考試課程名稱考 試考 查學 科 專 業(yè)學 號姓 名題 題目序號12345678910總 總計評卷 評卷教師各題分數(shù)Preparation of Polysaccharide-coating Type Chiral Stationary PhasesSince 1980s, chiral high-performance liquid chromatography(HPLC) for separating the enantiomers of racemates has attracted increasing a

2、ttention (Petersen 2015, Lorenz, SeidelMorgenstern 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

3、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, SeidelMorgenstern 2014, Martens, Bhushan 2014). In this field, the major works are concerning the development of various types of CSPs, which

4、are desired to separate the enantiomers of a wide range of chiral compounds (Guntari, Nam et al. 2014, Kreituss, Bode 2016, Potka, Biziuk et al. 2014, Poiger, Muller et al. 2015, Suliman, Elbashir et al. 2015, Suzuki, Han et al. 2015). Generally the well-known CSPs are prepared by coating polysaccha

5、ride 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, Thbault et al. 2016

6、, 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, SeidelMorgenstern 20

7、14, 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 polysaccharid

8、e derivatives, are applied worldwide in pharmaceutical industry and in research (Potka, 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

9、 (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 cellulose tribenzoate and its derivatives with different substituents on the phenyl groups. Afterwards, the colu

10、mns 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 co

11、mmon 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 -base, which tends to interact with -acid of chiral compounds(Tan, Fan et al. 2014). In addition, appropriate ster

12、ic 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 analy

13、tes (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. 2016). Thus,

14、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-dime

15、thylbenzoate) on silica gel addressed our investigations to alternative procedures, i.e. a polysaccharide was 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 (Daghi

16、r-Wojtkowiak, Studziska 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

17、 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).Refe

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