• 中国精品科技期刊
  • 中国高校百佳科技期刊
  • 中国中文核心期刊
  • 中国科学引文数据库核心期刊
Advanced Search
WU Xuri, FAN Yu, CHEN Yijun. Chromatographic separation of aryl alcohol enantiomers by cellulose tris(3, 5-dimethylphenylcarbamate)-based column[J]. Journal of China Pharmaceutical University, 2014, 45(2): 213-220. DOI: 10.11665/j.issn.1000-5048.20140215
Citation: WU Xuri, FAN Yu, CHEN Yijun. Chromatographic separation of aryl alcohol enantiomers by cellulose tris(3, 5-dimethylphenylcarbamate)-based column[J]. Journal of China Pharmaceutical University, 2014, 45(2): 213-220. DOI: 10.11665/j.issn.1000-5048.20140215

Chromatographic separation of aryl alcohol enantiomers by cellulose tris(3, 5-dimethylphenylcarbamate)-based column

More Information
  • The determination of absolute configuration of chiral compounds is typically a prerequisite for various investigations. In the present study, a Chiralcel OD-RH column coated with cellulose tris(3, 5-dimethylphenylcarbamate)(CDMPC)was used to evaluate the capability of enantiomeric separation of chiral aryl alcohols with a reversed phase HPLC. Results showed that the chromatographic behaviors, in terms of elution order, were closely correlated with absolute configurations of the chiral aryl alcohols. Therefore, this simple HPLC method can serve as an alternative approach to facilitate the determination of absolute configurations of chiral aryl alcohols according to their elution orders. To rule out the possibility of false assignments, the underlying mechanism of this chromatographic behavior was further studied by IR and NMR. Hydrogen bondings between C=O, NH in the chiral cavity of CDMPC and different enantiomers were the key factor for the respective recognition and elution orders.
  • [1]
    Shimazawa R,Nagai N,Toyoshima S,et al.Present state of new chiral drug developmentandreview in Japan[J].J Health Sci,2008,54(1):23-29.
    [2]
    Agranat I,Caner H,Caldwell J.Putting chirality to work:the strategy of chiral switches[J].Nat Rev Drug Disc,2002,1(10):753-768.
    [3]
    Okamoto Y.Yashima E.Polysaccharide derivatives for chromatographic separation of enantiomers[J].Angew Chem Int Ed,1998,37(8):1 020-1 043.
    [4]
    Yashima E,Yamamoto C,Okamoto Y.Polysaccharide-based chiral LC columns[J].Synlett,1998,(4):344-360.
    [5]
    Yashima E. Polysaccharide-based chiral stationary phases for high-performance liquid chromatographic enantioseparation[J].J Chromatogr A,2001,906(1/2):105-125.
    [6]
    Okamoto Y,Ikai T.Chiral HPLC for efficient resolution of enantiomers[J].Chem Soc Rev,2008,37(12):2 593-2 608.
    [7]
    Kasat RB,Linda Wang NH,Franses EI.Experimental probing and modeling of key sorbent-solute interactions of norephedrine enantiomers with polysaccharide-based chiral stationary phases[J].J Chromatogr A,2008,1 190(1/2):110-119.
    [8]
    Younes AA,Mangelings D,Vander Heyden Y.Chiral separations in reversed-phase liquid chromatography:evaluation of several polysaccharide- based chiral stationary phases for a separation strategy update[J].J Chromatogr A,2012,1 269:154-167.
    [9]
    Lv CG,Zhou ZQ.Chiral HPLC separation and absolute configuration assignment of a series of new triazole compounds[J].J Sep Sci,2011,34(4):363-370.
    [10]
    Lämmerhofer M,Pell R,Mahut M,et al.Enantiomer separation and indirect chromatographic absolute configuration prediction of chiral pirinixic acid derivatives:limitations of polysaccharide-type chiral stationary phases in comparison to chiral anion-exchangers[J].J Chromatogr A,2010,1 217(7):1 033-1 040.
    [11]
    Zhan FP,Yu GY,Yao BX,et al.Solvent effect in the chromatographic enantioseparation of 1,1′-bi-2-naphthol on a polysaccharide-based chiral stationary phase[J].J Chromatogr A,2010,1 217(26):4 278-4 284.
    [12]
    Yao BX,Zhan FP,Yu GY,et al.Temperature-induced inversion of elution order in the chromatographic enantioseparation of 1,1′-bi-2-naphthol on an immobilized polysaccharide-based chiral stationary phase[J].J Chromatogr A,2009,1 216(28):5 429-5 435.
    [13]
    Wu XR,Wang YC,Ju JM,et al.Enantioselective synthesis of ethyl(S)-2-hydroxy-4-phenylbutyrate by recombinant diketoreductase[J].Tetrahedron:Asymmetry,2009,20(21):2 504-2 509.
    [14]
    Stringham RW,Blackwell JA.“Entropically driven” chiral separations in supercritical fluid chromatography.Confirmation of isoelution temperature and reversal of elution order[J].Anal Chem,1996,68(13):2 179-2 185.
    [15]
    Okamoto Y,Kawashima M,Hatada K.Controlled chiral recognition of cellulose triphenylcarbamate derivatives as stationary phases for HPLC[J].J Chromatogr A,1986,363(2):173-186.
    [16]
    Yamamoto C,Yashima E,Okamoto Y.Computational studies on chiral discrimination mechanism of phenylcarbamate derivatives of cellulose[J].Bull Chem Soc Jpn,1999,72(8):1 815-1 825.
    [17]
    Thunberg L,Hashemi J,Andersson S.Comparative study of coated and immobilized polysaccharide-based chiral stationary phases and their applicability in the resolution of enantiomers[J].J Chromatogr B,2008,875(1):72-80.
    [18]
    Ilisz I,Pataj Z,Berkecz R,et al.High-performance liquid chromatographic enantioseparation of aminonaphthol analogs on polysaccharide-based chiral stationary phases[J].J Chromatogr A,2010,1 217(17):2 980-2 985.
    [19]
    Zhang T,Nguyen D,Franco P.Reversed-phase screening strategies for liquid chromatography on polysaccharide-derived chiral stationary phases[J].J Chromatogr A,2010,1 217(7):1 048-1 055.
    [20]
    Gebreyohannes KG,McGuffin VL.Thermodynamic and kinetic study of chiral separations of coumarin-based anticoagulants on derivatized amylose stationary phase[J].J Chromatogr A,2010,1 217(38):5 901-5 912.
    [21]
    Kasat RB,Wee SY,Loh JX,et al.Effect of the solute molecular structure on its enantioresolution on cellulose tris(3,5- dimethylphenylcarbamate)[J].J Chromatogr B,2008,875(1):81-92.
    [22]
    Yamamoto C,Yashima E,Okamoto Y.Structural analysis of amylose tris(3,5-dimethylphenylcarbamate)by NMR relevant to its chiral recognition mechanism in HPLC[J].J Am Chem Soc,2002,124(42):12 583-12 589.
  • Related Articles

    [1]SHI Min, YONG Qin, HE Yingna, HUANG Shiqin, ZHAO Xuan, YU Xian. Construction and in vivo evaluation of a thermosensitive hydrogel system loading with Pseudomonas aeruginosa DNA vaccine[J]. Journal of China Pharmaceutical University, 2021, 52(2): 186-194. DOI: 10.11665/j.issn.1000-5048.20210207
    [2]CHEN Ye, YIN Jun, YAO Wenbing, GAO Xiangdong. Advances of DNA-based nanomaterials in tumor therapy[J]. Journal of China Pharmaceutical University, 2020, 51(4): 406-417. DOI: 10.11665/j.issn.1000-5048.20200404
    [3]WANG Rui, WANG Yongmei, CAI Mingjun, KE Xuejia, WU Yue, CHONG Jun, CAO Rongyue. Pharmacological effects of anti-melanoma DC vaccine sensitized by fusion proteins of G3G6 and HST1[J]. Journal of China Pharmaceutical University, 2019, 50(2): 238-245. DOI: 10.11665/j.issn.1000-5048.20190216
    [4]HAN Xiu, QI Xiaole, WU Zhenghong. Advances in self-assemblied DNA nanocages as drug delivery systems[J]. Journal of China Pharmaceutical University, 2017, 48(6): 663-669. DOI: 10.11665/j.issn.1000-5048.20170605
    [5]ZHANG Zhiqing, WANG Fang, ZHOU Ting, ZHANG Guodong, WANG Xiufeng, LI Yunze. A DNA polyaptamer system as a targeted antitumor drug delivery[J]. Journal of China Pharmaceutical University, 2015, 46(4). DOI: 10.11665/j.issn.1000-5048.20150408
    [6]Formula optimization and transfection efficiency of polyethyleneimine/DNA complexes[J]. Journal of China Pharmaceutical University, 2010, 41(1): 40-44.
    [7]Study on the Flavonoids from Lonicera confusa DC.[J]. Journal of China Pharmaceutical University, 2004, (4): 9-12.
    [8]Applications of Au Nanoparticles Labeling Method in DNA-detection and the Technology of Genechip[J]. Journal of China Pharmaceutical University, 2003, (2): 88-93.
    [9]The Isoquinolones from Menispermum dauricum DC.[J]. Journal of China Pharmaceutical University, 2001, (2): 16-17.
    [10]Ptotoplast Transformation of Staphylococcal DNA[J]. Journal of China Pharmaceutical University, 1992, (4): 239-242.

Catalog

    Article views (1212) PDF downloads (1676) Cited by()

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return