메뉴 건너뛰기




Volumn 76, Issue , 2013, Pages 183-191

Development of the high-performance liquid chromatographic method for the enantioseparation of unusual glycine ester analogs on polysaccharide-based chiral stationary phases

Author keywords

Column liquid chromatography; Enantiomer separation; Gly analogs; Lux Amylose 2 column; Lux Cellulose columns

Indexed keywords

2 PROPYL 2 AMINO 2 (1 HYDROXYNAPHTHALEN 2 YL)ACETATE; 2 PROPYL 2 AMINO 2 (2 HYDROXYNAPHTHALEN 1 YL)ACETATE; ALCOHOL; AMYLOSE TRIS(5 CHLORO 2 METHYLPHENYLCARBAMATE); CARBAMIC ACID DERIVATIVE; CELLULOSE TRIS(3 CHLORO 4 METHYLPHENYLCARBAMATE); CELLULOSE TRIS(3,5 DIMETHYLPHENYLCARBAMATE); CELLULOSE TRIS(4 CHLORO 3 METHYLPHENYLCARBAMATE); CELLULOSE TRIS(4 METHYLBENZOATE); DIETHYLAMINE; ESTER DERIVATIVE; GLYCINE DERIVATIVE; HEPTANE; POLYSACCHARIDE; PROPYL 2 AMINO 2 (1 HYDROXYNAPHTHALEN 2 YL)ACETATE; PROPYL 2 AMINO 2 (2 HYDROXYNAPHTHALEN 1 YL)ACETATE; UNCLASSIFIED DRUG;

EID: 84872460722     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2012.12.030     Document Type: Article
Times cited : (4)

References (39)
  • 1
    • 0035897085 scopus 로고    scopus 로고
    • Vinylogous Mannich reactions: selectivity and synthetic utility
    • Bur S.K., Martin S.F. Vinylogous Mannich reactions: selectivity and synthetic utility. Tetrahedron 2001, 57:3221-3242.
    • (2001) Tetrahedron , vol.57 , pp. 3221-3242
    • Bur, S.K.1    Martin, S.F.2
  • 2
    • 0034835317 scopus 로고    scopus 로고
    • Biogenetically inspired approach to the strychnos alkaloids. Concise syntheses of (±)-akuammicine and (±)-strychnine
    • Ito M., Clark C.W., Mortimore M., Goh J.B., Martin S.F. Biogenetically inspired approach to the strychnos alkaloids. Concise syntheses of (±)-akuammicine and (±)-strychnine. J. Am. Chem. Soc. 2001, 123:8003-8010.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 8003-8010
    • Ito, M.1    Clark, C.W.2    Mortimore, M.3    Goh, J.B.4    Martin, S.F.5
  • 3
    • 30344438091 scopus 로고    scopus 로고
    • Syntheses and transformations of 1-(α-aminobenzyl)-2-naphthol derivatives
    • Szatmári I., Fülöp F. Syntheses and transformations of 1-(α-aminobenzyl)-2-naphthol derivatives. Curr. Org. Synth. 2004, 1:155-165.
    • (2004) Curr. Org. Synth. , vol.1 , pp. 155-165
    • Szatmári, I.1    Fülöp, F.2
  • 4
    • 33745645832 scopus 로고    scopus 로고
    • Discovery of a nanomolar inhibitor of the human murine double minute 2 (MDM2)-p53 interaction through an integrated, virtual database screening strategy
    • Lu Y., Nikolovska-Coleska Z., Fang X., Gao W., Shangary S., Qiu S., Qin D., Wang S. Discovery of a nanomolar inhibitor of the human murine double minute 2 (MDM2)-p53 interaction through an integrated, virtual database screening strategy. J. Med. Chem. 2006, 49:3759-3762.
    • (2006) J. Med. Chem. , vol.49 , pp. 3759-3762
    • Lu, Y.1    Nikolovska-Coleska, Z.2    Fang, X.3    Gao, W.4    Shangary, S.5    Qiu, S.6    Qin, D.7    Wang, S.8
  • 6
    • 60549083542 scopus 로고    scopus 로고
    • Discovery of human macrophage migration inhibitory factor (MIF)-CD74 antagonists via virtual screening
    • Cournia Z., Leng L., Gandavadi S., Du X., Bucala R., Jorgensen W.L. Discovery of human macrophage migration inhibitory factor (MIF)-CD74 antagonists via virtual screening. J. Med. Chem. 2009, 52:416-424.
    • (2009) J. Med. Chem. , vol.52 , pp. 416-424
    • Cournia, Z.1    Leng, L.2    Gandavadi, S.3    Du, X.4    Bucala, R.5    Jorgensen, W.L.6
  • 7
    • 0021686550 scopus 로고
    • Antibacterial studies of 7-(α-substituted sulphonamide)methyl- and 7-(α-substituted sulphonamide)phenyl-8-hydroxyquinolines
    • Chaturvedi K.K., Goyal M. Antibacterial studies of 7-(α-substituted sulphonamide)methyl- and 7-(α-substituted sulphonamide)phenyl-8-hydroxyquinolines. J. Indian Chem. Soc. 1984, 61:175-176.
    • (1984) J. Indian Chem. Soc. , vol.61 , pp. 175-176
    • Chaturvedi, K.K.1    Goyal, M.2
  • 10
    • 0033571566 scopus 로고    scopus 로고
    • Synthesis and evaluation of benzoxazinones as HIV-1 reverse transcriptase inhibitors. Analogs of efavirenz
    • Patel M., McHugh R.J., Beverly J. Synthesis and evaluation of benzoxazinones as HIV-1 reverse transcriptase inhibitors. Analogs of efavirenz. Bioorg. Med. Chem. Lett. 1999, 9:3221-3224.
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 3221-3224
    • Patel, M.1    McHugh, R.J.2    Beverly, J.3
  • 11
    • 0033972803 scopus 로고    scopus 로고
    • The herpesvirus proteases as targets for antiviral chemotherapy
    • Waxman L., Darke P.L. The herpesvirus proteases as targets for antiviral chemotherapy. Antiviral Chem. Chemother. 2000, 11:1-22.
    • (2000) Antiviral Chem. Chemother. , vol.11 , pp. 1-22
    • Waxman, L.1    Darke, P.L.2
  • 12
    • 0034126518 scopus 로고    scopus 로고
    • New 1,3-benzoxazin-2-ones or thiones of molluscacidal activity
    • Girgis A.S. New 1,3-benzoxazin-2-ones or thiones of molluscacidal activity. Pharmazie 2000, 55:426-428.
    • (2000) Pharmazie , vol.55 , pp. 426-428
    • Girgis, A.S.1
  • 13
    • 0019997677 scopus 로고
    • Carbonyl and thiocarbonyl compounds. XIX. Intramolecular cyclization of (2-nitroethanyl)aryl N-arylcarbamates: synthesis of newer series of 3,4-dihydro-2H-1,3-oxazin-2-ones and their antimicrobial activities
    • Latif N., Mishriky N., Assad F.M. Carbonyl and thiocarbonyl compounds. XIX. Intramolecular cyclization of (2-nitroethanyl)aryl N-arylcarbamates: synthesis of newer series of 3,4-dihydro-2H-1,3-oxazin-2-ones and their antimicrobial activities. Aust. J. Chem. 1982, 35:1037-1043.
    • (1982) Aust. J. Chem. , vol.35 , pp. 1037-1043
    • Latif, N.1    Mishriky, N.2    Assad, F.M.3
  • 15
    • 84862771544 scopus 로고    scopus 로고
    • Preparative scale isolation, purification and derivatization of mimosine, a non-proteinogenic amino acid
    • Nokihara K., Hirata A., Sogon T., Ohyama T. Preparative scale isolation, purification and derivatization of mimosine, a non-proteinogenic amino acid. Amino Acids 2012, 43:475-482.
    • (2012) Amino Acids , vol.43 , pp. 475-482
    • Nokihara, K.1    Hirata, A.2    Sogon, T.3    Ohyama, T.4
  • 16
    • 79961126927 scopus 로고    scopus 로고
    • Synthesis of hydroxynaphthyl-substituted alpha-amino acid derivatives via a modified Mannich reaction
    • Csütörtöki R., Szatmári I., Mándi A., Kurtán T., Fülöp F. Synthesis of hydroxynaphthyl-substituted alpha-amino acid derivatives via a modified Mannich reaction. Synlett 2011, 13:1940-1946.
    • (2011) Synlett , vol.13 , pp. 1940-1946
    • Csütörtöki, R.1    Szatmári, I.2    Mándi, A.3    Kurtán, T.4    Fülöp, F.5
  • 17
    • 30344459117 scopus 로고    scopus 로고
    • Structural and temperature effects in the high-performance liquid chromatographic enantioseparation of 1-(α-aminobenzyl)-2 naphthol and 2-(α-aminobenzyl)-1-naphthol analogs
    • Sztojkov-Ivanov A., Szatmári I., Péter A., Fülöp F. Structural and temperature effects in the high-performance liquid chromatographic enantioseparation of 1-(α-aminobenzyl)-2 naphthol and 2-(α-aminobenzyl)-1-naphthol analogs. J. Sep. Sci. 2005, 28:2505-2510.
    • (2005) J. Sep. Sci. , vol.28 , pp. 2505-2510
    • Sztojkov-Ivanov, A.1    Szatmári, I.2    Péter, A.3    Fülöp, F.4
  • 18
    • 34247643109 scopus 로고    scopus 로고
    • High-performance liquid chromatographic enantioseparation of 1-(aminoalkyl)-2-naphthol analogs on polysaccharide based chiral stationary phases
    • Sztojkov-Ivanov A., Tóth D., Szatmári I., Fülöp F., Péter A. High-performance liquid chromatographic enantioseparation of 1-(aminoalkyl)-2-naphthol analogs on polysaccharide based chiral stationary phases. Chirality 2007, 19:374-379.
    • (2007) Chirality , vol.19 , pp. 374-379
    • Sztojkov-Ivanov, A.1    Tóth, D.2    Szatmári, I.3    Fülöp, F.4    Péter, A.5
  • 19
    • 77953715121 scopus 로고    scopus 로고
    • High-performance liquid chromatographic enantioseparation of aminonaphthol analogs on polysaccharide-based chiral stationary phases
    • Ilisz I., Pataj Z., Berkecz R., Szatmári I., Fülöp F., Péter A. High-performance liquid chromatographic enantioseparation of aminonaphthol analogs on polysaccharide-based chiral stationary phases. J. Chromatogr. A 2010, 1217:2980-2985.
    • (2010) J. Chromatogr. A , vol.1217 , pp. 2980-2985
    • Ilisz, I.1    Pataj, Z.2    Berkecz, R.3    Szatmári, I.4    Fülöp, F.5    Péter, A.6
  • 20
    • 70349303201 scopus 로고    scopus 로고
    • Comparison of separation performances of cellulose-based chiral stationary phases in LC enantioseparation of aminonaphthol analogues
    • Ilisz I., Pataj Z., Berkecz R., Szatmári I., Fülöp F., Péter A. Comparison of separation performances of cellulose-based chiral stationary phases in LC enantioseparation of aminonaphthol analogues. Chromatographia 2009, 70:723-729.
    • (2009) Chromatographia , vol.70 , pp. 723-729
    • Ilisz, I.1    Pataj, Z.2    Berkecz, R.3    Szatmári, I.4    Fülöp, F.5    Péter, A.6
  • 21
    • 33847613572 scopus 로고    scopus 로고
    • HPLC enantioseparation of 1-(α-aminobenzyl)-2-naphthol an 2-(α-aminobenzyl)-1-naphthol analogs on a β-cyclodextrin-based chiral stationary phase
    • Berkecz R., Ilisz I., Sztojkov-Ivanov A., Szatmári I., Fülöp F., Armstrong D.W., Péter A. HPLC enantioseparation of 1-(α-aminobenzyl)-2-naphthol an 2-(α-aminobenzyl)-1-naphthol analogs on a β-cyclodextrin-based chiral stationary phase. Chromatographia 2007, 65:337-341.
    • (2007) Chromatographia , vol.65 , pp. 337-341
    • Berkecz, R.1    Ilisz, I.2    Sztojkov-Ivanov, A.3    Szatmári, I.4    Fülöp, F.5    Armstrong, D.W.6    Péter, A.7
  • 23
    • 0028340483 scopus 로고
    • Chloro-methylphenylcarbamate derivatives of cellulose as chiral stationary phases for high performance liquid chromatography
    • Chankvetadze B., Yashima E., Okamoto J.Y. Chloro-methylphenylcarbamate derivatives of cellulose as chiral stationary phases for high performance liquid chromatography. J. Chromatogr. A 1994, 670:39-49.
    • (1994) J. Chromatogr. A , vol.670 , pp. 39-49
    • Chankvetadze, B.1    Yashima, E.2    Okamoto, J.Y.3
  • 24
    • 0028935002 scopus 로고
    • Dimethyl-, dichloro- and chloromethylphenylcarbamates of amylose as chiral stationary phases for high-performance liquid chromatography
    • Chankvetadze B., Yashima E., Okamoto J.Y. Dimethyl-, dichloro- and chloromethylphenylcarbamates of amylose as chiral stationary phases for high-performance liquid chromatography. J. Chromatogr. A 1995, 694:101-109.
    • (1995) J. Chromatogr. A , vol.694 , pp. 101-109
    • Chankvetadze, B.1    Yashima, E.2    Okamoto, J.Y.3
  • 25
    • 0030731814 scopus 로고    scopus 로고
    • 3-Fluoro-, 3-chloro- and 3-bromo-5-methylphenylcarbamates of cellulose and amylose as chiral stationary phases for high-performance liquid chromatographic enantioseparation
    • Chankvetadze B., Chankvetadze L., Sidamonidze Sh., Kasashima E., Yashima E., Okamoto Y. 3-Fluoro-, 3-chloro- and 3-bromo-5-methylphenylcarbamates of cellulose and amylose as chiral stationary phases for high-performance liquid chromatographic enantioseparation. J. Chromatogr. A 1997, 787:67-77.
    • (1997) J. Chromatogr. A , vol.787 , pp. 67-77
    • Chankvetadze, B.1    Chankvetadze, L.2    Sidamonidze, S.3    Kasashima, E.4    Yashima, E.5    Okamoto, Y.6
  • 27
    • 0030176327 scopus 로고    scopus 로고
    • High performance liquid chromatography enantioseparation of chiral pharmaceuticals using tris(chloro-methylphenylcarbamate)s of cellulose
    • Chankvetadze B., Chankvetadze L., Sidamonidze Sh., Yashima E., Okamoto J.Y. High performance liquid chromatography enantioseparation of chiral pharmaceuticals using tris(chloro-methylphenylcarbamate)s of cellulose. J. Pharm. Biomed. Anal. 1996, 14:1295-1303.
    • (1996) J. Pharm. Biomed. Anal. , vol.14 , pp. 1295-1303
    • Chankvetadze, B.1    Chankvetadze, L.2    Sidamonidze, S.3    Yashima, E.4    Okamoto, J.Y.5
  • 28
    • 77953558794 scopus 로고    scopus 로고
    • Optimization of the LC enantioseparation of chiral pharmaceuticals using cellulose tris(4 chloro-3-methylphenylcarbamate) as chiral selector and polar non-aqueous mobile phases
    • Dossou K.S.S., Chiap P., Chankvetadze B., Servais A.C., Fillet M., Crommen J. Optimization of the LC enantioseparation of chiral pharmaceuticals using cellulose tris(4 chloro-3-methylphenylcarbamate) as chiral selector and polar non-aqueous mobile phases. J. Sep. Sci. 2010, 33:1699-1707.
    • (2010) J. Sep. Sci. , vol.33 , pp. 1699-1707
    • Dossou, K.S.S.1    Chiap, P.2    Chankvetadze, B.3    Servais, A.C.4    Fillet, M.5    Crommen, J.6
  • 29
    • 79959206419 scopus 로고    scopus 로고
    • Comparative enantioseparation of pharmaceuticals in capillary electrochomatography on polysaccharide based chiral stationary phases containing selectors with or without chlorinated derivatives
    • Hendrickx A., Mangelings D., Chankvetadze B., Heyden Y.V. Comparative enantioseparation of pharmaceuticals in capillary electrochomatography on polysaccharide based chiral stationary phases containing selectors with or without chlorinated derivatives. Electrophoresis 2010, 31:3207-3216.
    • (2010) Electrophoresis , vol.31 , pp. 3207-3216
    • Hendrickx, A.1    Mangelings, D.2    Chankvetadze, B.3    Heyden, Y.V.4
  • 30
    • 70349768267 scopus 로고    scopus 로고
    • Enantioresolution of basic pharmaceuticals using cellulose tris(4-chloro-3 methylphenylcarbamate) as chiral stationary phase and polar organic mobile phases
    • Dossou K.S.S., Chiap P., Chankvetadze B., Servais A.C., Fillet M., Crommen J. Enantioresolution of basic pharmaceuticals using cellulose tris(4-chloro-3 methylphenylcarbamate) as chiral stationary phase and polar organic mobile phases. J. Chromatogr. A 2009, 1216:7450-7455.
    • (2009) J. Chromatogr. A , vol.1216 , pp. 7450-7455
    • Dossou, K.S.S.1    Chiap, P.2    Chankvetadze, B.3    Servais, A.C.4    Fillet, M.5    Crommen, J.6
  • 31
    • 0030901324 scopus 로고    scopus 로고
    • Thermodynamic study of an unusual chiral separation. Propanolol enantiomers on an immobilized cellulose
    • Fornstedt T., Sajonz P., Guichon G. Thermodynamic study of an unusual chiral separation. Propanolol enantiomers on an immobilized cellulose. J. Am. Chem. Soc. 1997, 119:1254-1264.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 1254-1264
    • Fornstedt, T.1    Sajonz, P.2    Guichon, G.3
  • 32
    • 0000383098 scopus 로고
    • Chiral recognition in the resolution of enantiomers by GLC
    • Koppenhoefer B., Bayer E. Chiral recognition in the resolution of enantiomers by GLC. Chromatographia 1984, 19:123-130.
    • (1984) Chromatographia , vol.19 , pp. 123-130
    • Koppenhoefer, B.1    Bayer, E.2
  • 33
    • 0002910705 scopus 로고
    • Evidence for a temperature dependent reversal of enantioselectivity in complexation gas chromatography on chiral phases
    • Schurig V., Ossig J., Link R. Evidence for a temperature dependent reversal of enantioselectivity in complexation gas chromatography on chiral phases. Angew. Chem. 1989, 101:197-200.
    • (1989) Angew. Chem. , vol.101 , pp. 197-200
    • Schurig, V.1    Ossig, J.2    Link, R.3
  • 34
    • 0000352907 scopus 로고    scopus 로고
    • Chromatography on chiral carriers
    • Allenmark S., Schurig V. Chromatography on chiral carriers. J. Mater. Chem. 1997, 7:1955-1963.
    • (1997) J. Mater. Chem. , vol.7 , pp. 1955-1963
    • Allenmark, S.1    Schurig, V.2
  • 35
    • 0037506742 scopus 로고    scopus 로고
    • Comparison of two methods for the gas chromatographic determination of thermodynamic parameters of enantioselectivity
    • Spanik I., Krupcik J., Schurig V. Comparison of two methods for the gas chromatographic determination of thermodynamic parameters of enantioselectivity. J. Chromatogr. A 1999, 843:123-128.
    • (1999) J. Chromatogr. A , vol.843 , pp. 123-128
    • Spanik, I.1    Krupcik, J.2    Schurig, V.3
  • 36
    • 0039178096 scopus 로고    scopus 로고
    • Retention mechanism of β-blockers on an immobilized cellulase. Relative importance of the hydrophobic and ionic contributions to their enantioselective and nonselective interactions
    • Gotmar G., Fornstedt T., Guiochon G. Retention mechanism of β-blockers on an immobilized cellulase. Relative importance of the hydrophobic and ionic contributions to their enantioselective and nonselective interactions. Anal. Chem. 2000, 72:3908-3915.
    • (2000) Anal. Chem. , vol.72 , pp. 3908-3915
    • Gotmar, G.1    Fornstedt, T.2    Guiochon, G.3
  • 37
    • 1342286885 scopus 로고    scopus 로고
    • Study of mechanisms of chiral discrimination of amino acids and their derivatives on a teicoplanin based chiral stationary phase
    • Cavazzini A., Nadalini G., Dondi F., Gasparrini F., Ciogli A., Villani C. Study of mechanisms of chiral discrimination of amino acids and their derivatives on a teicoplanin based chiral stationary phase. J. Chromatogr. A 2004, 1031:143-158.
    • (2004) J. Chromatogr. A , vol.1031 , pp. 143-158
    • Cavazzini, A.1    Nadalini, G.2    Dondi, F.3    Gasparrini, F.4    Ciogli, A.5    Villani, C.6
  • 38
    • 0141569489 scopus 로고    scopus 로고
    • Effects of alcohol mobile-phase modifiers on the structure and chiral selectivity of amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase
    • Wang T., Wenslow R.M. Effects of alcohol mobile-phase modifiers on the structure and chiral selectivity of amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase. J. Chromatogr. A 2003, 1015:99-110.
    • (2003) J. Chromatogr. A , vol.1015 , pp. 99-110
    • Wang, T.1    Wenslow, R.M.2
  • 39
    • 37049081687 scopus 로고
    • Molecular mechanics and molecular shape. Part 4. Size, shape, and steric parameters
    • Meyer A.Z. Molecular mechanics and molecular shape. Part 4. Size, shape, and steric parameters. J. Chem. Soc. Perkin Trans. 1986, 2:1567-1572.
    • (1986) J. Chem. Soc. Perkin Trans. , vol.2 , pp. 1567-1572
    • Meyer, A.Z.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.