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1、武汉工程大学(硕士)研究生试卷(第 页)武 汉 工 程 大 学(硕士)研究生试卷本考试课程名称考 试考 查学 科 专 业学 号姓 名题 题目序号12345678910总 总计评卷 评卷教师各题分数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

18、rencesLorenz H., and SeidelMorgenstern 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

19、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., Ya

20、ng R., and Yuan L. M. Homochiral metalorganic framework used as a stationary phase for highperformance liquid chromatography. J Sep Sci 3区 (2.741), 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

21、 of racemic drugs based on homochiral metalorganic 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) base

22、d-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

23、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)Woods R. M., Patel D. C., Lim Y., Breitbach Z. S., Gao H., Keene C., Li G., Krti L., and Armstrong D. W. Enantiomeric separation of biaryl atropisomers using cyclofructan b

24、ased chiral stationary phases. J Chromatogr A 2区 (3.926), 2014, 1357: 172-81. (Times Cited: 27)Zhang Q., Gil V., Snchez-Lpez E., Garca M. ., Jiang Z., and Marina M. L. Evaluation of the potential of a quinidine-based monolithic column on the enantiomeric separation of herbicides by nano-liquid chrom

25、atography. Microchem J 3区 (2.893), 2015, 123: 15-21. (Times Cited: 2)Guntari S. N., Nam E., Pranata N. N., Chia K., Wong E. H., Blencowe A., Goh T. K., Caruso F., and Qiao G. G. Fabrication of Chiral Stationary Phases via Continuous Assembly of Polymers for Resolution of Enantiomers by Liquid Chroma

26、tography. Macromol Mater Eng 2区 (2.834), 2014, 299(11): 1285-91. (Times Cited: 2)Kreituss I., and Bode J. W. Catalytic Kinetic Resolution of Saturated N-Heterocycles by Enantioselective Amidation with Chiral Hydroxamic Acids. Acc Chem Res 1区 (22.003), 2016. (Times Cited: 0)Potka J. M., Biziuk M., Mo

27、rrison C., and Namienik J. Pharmaceutical and forensic drug applications of chiral supercritical fluid chromatography. TrAC Trends Anal Chem. 2区 (7.487), 2014, 56: 74-89. (Times Cited: 39)Poiger T., Muller M. D., Buser H. R., and Buerge I. J. Environmental behavior of the chiral herbicide haloxyfop.

28、 1. Rapid and preferential interconversion of the enantiomers in soil. J Agric Food Chem 1区 (2.857), 2015, 63(10): 2583-90. (Times Cited: 10)Suliman F. O., Elbashir A. A., and Schmitz O. J. Study on the separation of ofloxacin enantiomers by hydroxyl-propyl-cyclodextrin as a chiral selector in capil

29、lary electrophoresis: a computational approach. J Inclusion Phenom Macrocyclic Chem. 4区 (1.253), 2015, 83(1-2): 119-29. (Times Cited: 5)Suzuki Y., Han J., Kitagawa O., Acea J. L., Klika K. D., and Soloshonok V. A. A comprehensive examination of the self-disproportionation of enantiomers (SDE) of chi

30、ral amides via achiral, laboratory-routine, gravity-driven column chromatography. RSC Adv 2区 (3.286), 2015, 5(4): 2988-93. (Times Cited: 10)Chen W., Duan R., and Fan Q. C. Preparation and enantioseparation property of chiral stationary phases based on cellulose tris (3, 5-dimethylbenzoate)-A new way

31、 to prepare polysaccharide-coating type chiral stationary phases. Chin J Polym Sci 4区 (1.811), 2014, 32(4): 458-66. (Times Cited: 4)Mizuno K., and Kataoka H. Analysis of urinary 8-isoprostane as an oxidative stress biomarker by stable isotope dilution using automated online in-tube solid-phase micro

32、extraction coupled with liquid chromatographytandem mass spectrometry. J Pharm Biomed Anal 3区 (3.169), 2015, 112: 36-42. (Times Cited: 6)Junter G. A., Thbault P., and Lebrun L. Polysaccharide-based antibiofilm surfaces. Acta Biomater 1区 (6.008), 2016, 30: 13-25. (Times Cited: 10)Mohan T., Rathner R.

33、, Reishofer D., Koller M., Elschner T., Spirk S., Heinze T., Stana-Kleinschek K., and Kargl R. Designing hydrophobically modified polysaccharide derivatives for highly efficient enzyme immobilization. Biomacromolecules 2区 (5.583), 2015, 16(8): 2403-11. (Times Cited: 4)Shen J., Ikai T., and Okamoto Y

34、. Synthesis and application of immobilized polysaccharide-based chiral stationary phases for enantioseparation by high-performance liquid chromatography. J Chromatogr A 2区 (3.926), 2014, 1363: 51-61. (Times Cited: 9)Shen J., and Okamoto Y. Efficient Separation of Enantiomers Using Stereoregular Chir

35、al Polymers. Chem Rev 1区 (37.369), 2016, 116(3): 1094-138. (Times Cited: 45)Zhang C., Ma R., Wang H., Sakai R., Satoh T., Kakuchi T., Liu L., and Okamoto Y. Influence of Helical Structure on Chiral Recognition of Poly(phenylacetylene)s Bearing Phenylcarbamate Residues of L-Phenylglycinol and Amide L

36、inage as Pendants. Chirality 4区 (2.025), 2015, 27(8): 500-6. (Times Cited: 6)Zhang C., Wang H., Yang T., Ma R., Liu L., Sakai R., Satoh T., Kakuchi T., and Okamoto Y. Synthesis and chiral recognition of helical poly(phenylacetylene)s bearingl-phenylglycinol and its phenylcarbamates as pendants. J Po

37、lym Sci Part A: Polym Chem 3区 (3.114), 2015, 53(6): 809-21. (Times Cited: 6)Hu G., Huang M., Luo C., Wang Q., and Zou J. W. Interactions between pyrazole derived enantiomers and Chiralcel OJ: Prediction of enantiomer absolute configurations and elution order by molecular dynamics simulations. J Mol

38、Graphics Modell 4区 (1.674), 2016, 66: 123-32. (Times Cited: 0)Li H., Jiang X., Xu W., Chen Y., Yu W., and Xu J. Numerical determination of non-Langmuirian adsorption isotherms of ibuprofen enantiomers on Chiralcel OD column using ultravioletcircular dichroism dual detector. J Chromatogr A 2区 (3.926)

39、, 2016, 1435: 92-9. (Times Cited: 1)Okada Y., Yamamoto C., Kamigaito M., Gao Y., Shen J., and Okamoto Y. Enantioseparation Using Cellulose Tris (3, 5-dimethylphenylcarbamate) as Chiral Stationary Phase for HPLC: Influence of Molecular Weight of Cellulose. Molecules 3区 (2.465), 2016, 21(11): 1484. (T

40、imes Cited: 0)Tan Y., Fan J., Lin C., Tu H., Zheng S., and Zhang W. Synthesis and enantioseparation behaviors of novel immobilized 3, 5dimethylphenylcarbamoylated polysaccharide chiral stationary phases. J Sep Sci 3区 (2.741), 2014, 37(5): 488-94. (Times Cited: 9)Mu H., Wang B., Xu Z., Sun Y., Huang

41、X., Shen Y., Eremin S. A., Zherdev A. V., Dzantiev B. B., and Lei H. Stereospecific recognition and quantitative structureactivity relationship between antibodies and enantiomers: ofloxacin as a model hapten. Analyst 2区 (4.033), 2015, 140(4): 1037-45. (Times Cited: 2)Wang L., Chai Y., Ni Z., Wang L.

42、, Hu R., Pan Y., and Sun C. Qualitative and quantitative analysis of enantiomers by mass spectrometry: Application of a simple chiral chloride probe via rapid in-situ reaction. Anal Chim Acta 2区 (4.712), 2014, 809: 104-8. (Times Cited: 6)Wencel-Delord J., and Colobert F. Diastereoselective Substrate

43、-Controlled Transition-Metal-Catalyzed CH Activation: An Old Solution to a Modern Synthetic Challenge. Synlett 3区 (2.323), 2015, 26(19): 2644-58. (Times Cited: 7)Wencel-Delord J., Panossian A., Leroux F., and Colobert F. Recent advances and new concepts for the synthesis of axially stereoenriched bi

44、aryls. Chem Soc Rev 1区 (34.090), 2015, 44(11): 3418-30. (Times Cited: 16)Yu S., and Pu L. Recent progress on using BINOLs in enantioselective molecular recognition. Tetrahedron 3区 (2.645), 2015, 71(5): 745-72. (Times Cited: 45)Peluso P., Mamane V., Aubert E., and Cossu S. Insights into the impact of

45、 shape and electronic properties on the enantioseparation of polyhalogenated 4, 4-bipyridines on polysaccharide-type selectors. Evidence of stereoselective halogen bonding interactions. J Chromatogr A 2区 (3.926), 2014, 1345: 182-92. (Times Cited: 7)Sanganyado E., Lu Z., and Gan J. Mechanistic insigh

46、ts on chaotropic interactions of liophilic ions with basic pharmaceuticals in polar ionic mode liquid chromatography. J Chromatogr A 2区 (3.926), 2014, 1368: 82-8. (Times Cited: 4)Zhang T., Holder E., Franco P., and Lindner W. Zwitterionic chiral stationary phases based on cinchona and chiral sulfoni

47、c acids for the direct stereoselective separation of amino acids and other amphoteric compounds. J Sep Sci 3区 (2.741), 2014, 37(11): 1237-47. (Times Cited: 20)Zhou J., Tang J., and Tang W. Recent development of cationic cyclodextrins for chiral separation. TrAC Trends Anal Chem 2区 (7.487), 2015, 65:

48、 22-9. (Times Cited: 21)Kharaishvili Q., Jibuti G., Farkas T., and Chankvetadze B. Further proof to the utility of polysaccharide-based chiral selectors in combination with superficially porous silica particles as effective chiral stationary phases for separation of enantiomers in high-performance l

49、iquid chromatography. J Chromatogr A 2区 (3.926), 2016, 1467: 163-8. (Times Cited: 2)Fanali C., Fanali S., and Chankvetadze B. HPLC Separation of Enantiomers of Some Flavanone Derivatives Using Polysaccharide-Based Chiral Selectors Covalently Immobilized on Silica. Chromatographia 4区 (1.332), 2016, 7

50、9(3-4): 119-24. (Times Cited: 2)Gegenava M., Chankvetadze L., Farkas T., and Chankvetadze B. Enantioseparation of selected chiral sulfoxides in highperformance liquid chromatography with polysaccharidebased chiral selectors in polar organic mobile phases with emphasis on enantiomer elution order. J

51、Sep Sci 3区 (2.741), 2014, 37(9-10): 1083-8. (Times Cited: 11)Khater S., and West C. Insights into chiral recognition mechanisms in supercritical fluid chromatography V. Effect of the nature and proportion of alcohol mobile phase modifier with amylose and cellulose tris-(3, 5-dimethylphenylcarbamate)

52、 stationary phases. J Chromatogr A 2区 (3.926), 2014, 1373: 197-210. (Times Cited: 11)Liu R., Zhang Y., Bai L., Huang M., Chen J., and Zhang Y. Synthesis of cellulose-2, 3-bis (3, 5-dimethylphenylcarbamate) in an ionic liquid and its chiral separation efficiency as stationary phase. Int J Mol Sci 3区 (3.257), 2014, 15(4): 6161-8. (Times Cited: 4)Wang J., Xi J. B., Chen W., Huang S. H., and Bai Z. W. High performance chiral separation materials based on chitosan bis (3, 5-dimethylphenylcarbamate)-(alkyl urea) s. Carbohydr Polym 2区 (4.219), 2017, 156: 481-9. (Times Ci

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