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Volumn , Issue , 2010, Pages 33-52

Preparation and chiral recognition of polysaccharide-based selectors

Author keywords

Amylose; Cellulose; Chiral stationary phase; Enantioseparation; High performance liquid chromatography

Indexed keywords


EID: 84895236541     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-3-642-12445-7_2     Document Type: Chapter
Times cited : (12)

References (48)
  • 1
    • 37049126956 scopus 로고
    • Ligand chromatography on asymmetric complex-forming sorbents as a new method for resolution of racemates
    • Rogozhin SV, Davankov VA (1971) Ligand chromatography on asymmetric complex-forming sorbents as a new method for resolution of racemates. J Chem Soc Chem Commun 490-493
    • (1971) J Chem Soc Chem Commun , pp. 490-493
    • Rogozhin, S.V.1    Davankov, V.A.2
  • 2
    • 56549116899 scopus 로고    scopus 로고
    • Chiral HPLC for efficient resolution of enantiomers
    • Okamoto Y, Ikai T (2008) Chiral HPLC for efficient resolution of enantiomers. Chem Soc Rev 37:2593-2608
    • (2008) Chem Soc Rev , vol.37 , pp. 2593-2608
    • Okamoto, Y.1    Ikai, T.2
  • 3
    • 84895213888 scopus 로고    scopus 로고
    • Chiral separation techniques: A practical approach, 3rd completely revised and updated edn
    • Subramanian G (ed) (2007) Chiral separation techniques: a practical approach, 3rd completely revised and updated edn. Wiley-VCH, Weinheim
    • (2007) Wiley-VCH, Weinheim
    • Subramanian, G.1
  • 4
    • 0026834334 scopus 로고
    • Chiral separations by high-performance liquid chromatography
    • Taylor DR, Maher K (1992) Chiral separations by high-performance liquid chromatography. J Chromatogr Sci 30:67-85
    • (1992) J Chromatogr Sci , vol.30 , pp. 67-85
    • Taylor, D.R.1    Maher, K.2
  • 5
    • 11744286228 scopus 로고
    • Considerations of chiral recognition relevant to the liquidchromatographic separation of enantiomers
    • Pirkle WH, Pochapsky TC (1989) Considerations of chiral recognition relevant to the liquidchromatographic separation of enantiomers. Chem Rev 89:347-362
    • (1989) Chem Rev , vol.89 , pp. 347-362
    • Pirkle, W.H.1    Pochapsky, T.C.2
  • 6
    • 0023653722 scopus 로고
    • Optical isomer separation by liquid-chromatography
    • Armstrong DW (1987) Optical isomer separation by liquid-chromatography. Anal Chem 59:84A-91A
    • (1987) Anal Chem , vol.59
    • Armstrong, D.W.1
  • 7
    • 1542350269 scopus 로고    scopus 로고
    • Optically active polymers for chiral separation
    • Yamamoto C, Okamoto Y (2004) Optically active polymers for chiral separation. Bull Chem Soc Jpn 77:227-257
    • (2004) Bull Chem Soc Jpn , vol.77 , pp. 227-257
    • Yamamoto, C.1    Okamoto, Y.2
  • 8
    • 0035847276 scopus 로고    scopus 로고
    • Optically active synthetic polymers as chiral stationary phases in HPLC
    • Nakano T (2001) Optically active synthetic polymers as chiral stationary phases in HPLC. J Chromatogr A 906:205-225
    • (2001) J Chromatogr A , vol.906 , pp. 205-225
    • Nakano, T.1
  • 9
    • 36649036013 scopus 로고    scopus 로고
    • Polysaccharide derivatives as useful chiral stationary phases in high-performance liquid chromatography
    • Chen XM, Yamamoto C, Okamoto Y (2007) Polysaccharide derivatives as useful chiral stationary phases in high-performance liquid chromatography. Pure Appl Chem 79:1561-1573
    • (2007) Pure Appl Chem , vol.79 , pp. 1561-1573
    • Chen, X.M.1    Yamamoto, C.2    Okamoto, Y.3
  • 10
    • 0000936090 scopus 로고
    • Resolution into optical isomers of some amino acids by paper chromatography
    • Kotake M, Sakan T, Nakamura N, Senoh S (1951) Resolution into optical isomers of some amino acids by paper chromatography. J Am Chem Soc 73:2973-2974
    • (1951) J Am Chem Soc , vol.73 , pp. 2973-2974
    • Kotake, M.1    Sakan, T.2    Nakamura, N.3    Senoh, S.4
  • 11
    • 0001911122 scopus 로고
    • The optical resolution of aromatic amino-acids on paper chromatograms
    • Dalgliesh C (1952) The optical resolution of aromatic amino-acids on paper chromatograms. J Chem Soc 3940-3942
    • (1952) J Chem Soc , pp. 3940-3942
    • Dalgliesh, C.1
  • 12
    • 84985566376 scopus 로고
    • Complete enantiomer separation by chromatography on potato starch
    • Hess H, Burger G, Musso H (1978) Complete enantiomer separation by chromatography on potato starch. Angew Chem Int Ed 17:612-614
    • (1978) Angew Chem Int Ed , vol.17 , pp. 612-614
    • Hess, H.1    Burger, G.2    Musso, H.3
  • 13
    • 0015800169 scopus 로고
    • A complete separation of a racemic mixture by elution chromatography on cellulose triacetate
    • Hesse G, Hagel R (1973) A complete separation of a racemic mixture by elution chromatography on cellulose triacetate. Chromatographia 6:277-280
    • (1973) Chromatographia , vol.6 , pp. 277-280
    • Hesse, G.1    Hagel, R.2
  • 14
    • 0000915204 scopus 로고
    • Useful chiral packing materials for high-performance liquid chromatographic resolution cellulose triacetate and tribenzoate coated on macroporous silica gel
    • Okamoto Y, Kawashima M, Yamamoto K, Hatada K (1984) Useful chiral packing materials for high-performance liquid chromatographic resolution cellulose triacetate and tribenzoate coated on macroporous silica gel. Chem Lett 13:739-742
    • (1984) Chem Lett , vol.13 , pp. 739-742
    • Okamoto, Y.1    Kawashima, M.2    Yamamoto, K.3    Hatada, K.4
  • 16
    • 0006598577 scopus 로고
    • Chromatographic chiral resolution XIV-cellulose tribenzoate derivatives as chiral stationary phases for high-performance liquid chromatography
    • Okamoto Y, Aburatani R, Hatada K (1987) Chromatographic chiral resolution XIV-cellulose tribenzoate derivatives as chiral stationary phases for high-performance liquid chromatography. J Chromatogr 389:95-102
    • (1987) J Chromatogr , vol.389 , pp. 95-102
    • Okamoto, Y.1    Aburatani, R.2    Hatada, K.3
  • 17
    • 0028331505 scopus 로고
    • Resolution by high-performance liquid chromatography using polysaccharide carbamates and benzoates as chiral stationary phases
    • Okamoto Y, Kaida Y (1994) Resolution by high-performance liquid chromatography using polysaccharide carbamates and benzoates as chiral stationary phases. J Chromatogr A 666:403-419
    • (1994) J Chromatogr A , vol.666 , pp. 403-419
    • Okamoto, Y.1    Kaida, Y.2
  • 18
    • 26844485913 scopus 로고    scopus 로고
    • Polysaccharide-based chiral LC columns
    • Yashima E, Yamamoto C, Okamoto Y (1998) Polysaccharide-based chiral LC columns. Synlett 344-360
    • (1998) Synlett , pp. 344-360
    • Yashima, E.1    Yamamoto, C.2    Okamoto, Y.3
  • 19
    • 0012003562 scopus 로고
    • Useful chiral packing materials for highperformance liquid chromatographic resolution of enantiomers: Phenylcarbamates of polysaccharides coated on silica gel
    • Okamoto Y, Kawashima M, Hatada K (1984) Useful chiral packing materials for highperformance liquid chromatographic resolution of enantiomers: phenylcarbamates of polysaccharides coated on silica gel. J Am Chem Soc 106:5357-5359
    • (1984) J Am Chem Soc , vol.106 , pp. 5357-5359
    • Okamoto, Y.1    Kawashima, M.2    Hatada, K.3
  • 20
    • 0002642210 scopus 로고
    • Controlled chiral recognition of cellulose triphenylcarbamate derivatives supported on silica gel
    • Okamoto Y, Kawashima M, Hatada K (1986) Controlled chiral recognition of cellulose triphenylcarbamate derivatives supported on silica gel. J Chromatogr 363:173-186
    • (1986) J Chromatogr , vol.363 , pp. 173-186
    • Okamoto, Y.1    Kawashima, M.2    Hatada, K.3
  • 21
    • 0027137495 scopus 로고
    • Resolution of enantiomers by HPLC on tris(4-alkoxyphenylcarbamate)s of cellulose and amylase
    • Okamoto Y, Ohashi T, Kaida Y, Yashima E (1993) Resolution of enantiomers by HPLC on tris(4-alkoxyphenylcarbamate)s of cellulose and amylase. Chirality 5:616-621
    • (1993) Chirality , vol.5 , pp. 616-621
    • Okamoto, Y.1    Ohashi, T.2    Kaida, Y.3    Yashima, E.4
  • 22
    • 0028340483 scopus 로고
    • Chloromethylphenylcarbamate derivatives of cellulose as chiral stationary phases for high-performance liquid chromatography
    • Chankvetadze B, Yashima E, Okamoto Y (1994) Chloromethylphenylcarbamate derivatives of cellulose as chiral stationary phases for high-performance liquid chromatography. J Chromatogr A 670:39-49
    • (1994) J Chromatogr A , vol.670 , pp. 39-49
    • Chankvetadze, B.1    Yashima, E.2    Okamoto, Y.3
  • 23
    • 0002640343 scopus 로고
    • Useful chiral stationary phases for HPLC amylose tris(3, 5-dimethylphenylcarbamate) and tris(3, 5-dichlorophenylcarbamate) supported on silica gel
    • Okamoto Y, Aburatani R, Fukumoto T, Hatada K (1987) Useful chiral stationary phases for HPLC amylose tris(3, 5-dimethylphenylcarbamate) and tris(3, 5-dichlorophenylcarbamate) supported on silica gel. Chem Lett 16:1857-1860
    • (1987) Chem Lett , vol.16 , pp. 1857-1860
    • Okamoto, Y.1    Aburatani, R.2    Fukumoto, T.3    Hatada, K.4
  • 24
    • 0028935002 scopus 로고
    • Dimethyl-, dichloro-and chloromethylphenylcarbamates of amylose as chiral stationary phases for HPLC
    • Chankvetadze B, Yashima E, Okamoto Y (1995) Dimethyl-, dichloro-and chloromethylphenylcarbamates of amylose as chiral stationary phases for HPLC. J Chromatogr A 694:101-109
    • (1995) J Chromatogr A , vol.694 , pp. 101-109
    • Chankvetadze, B.1    Yashima, E.2    Okamoto, Y.3
  • 25
    • 84966145738 scopus 로고
    • Enantioseparation on fluoro-methylphenylcarbamates of cellulose and amylose as chiral stationary phases for HPLC
    • Yashima E, Yamamoto C, Okamoto Y (1995) Enantioseparation on fluoro-methylphenylcarbamates of cellulose and amylose as chiral stationary phases for HPLC. Polym J 27: 856-861
    • (1995) Polym J , vol.27 , pp. 856-861
    • Yashima, E.1    Yamamoto, C.2    Okamoto, Y.3
  • 26
    • 0032767528 scopus 로고    scopus 로고
    • Computational studies on chiral discrimination mechanism of phenylcarbamate derivatives of cellulose
    • Yamamoto C, Yashima E, Okamoto Y (1999) Computational studies on chiral discrimination mechanism of phenylcarbamate derivatives of cellulose. Bull Chem Soc Jpn 72:1815-1825
    • (1999) Bull Chem Soc Jpn , vol.72 , pp. 1815-1825
    • Yamamoto, C.1    Yashima, E.2    Okamoto, Y.3
  • 27
    • 0035449458 scopus 로고    scopus 로고
    • Solid-state NMR characterization of amylose tris (3, 5- dimethylphenylcarbamate) chiral stationary-phase structure as a function of mobilephase composition
    • Wenslow RM, Wang T (2001) Solid-state NMR characterization of amylose tris (3, 5-dimethylphenylcarbamate) chiral stationary-phase structure as a function of mobilephase composition. Anal Chem 73:4190-4195
    • (2001) Anal Chem , vol.73 , pp. 4190-4195
    • Wenslow, R.M.1    Wang, T.2
  • 28
    • 0037164072 scopus 로고    scopus 로고
    • Structural analysis of amylose tris (3, 5-dimethylphenylcarbamate) by NMR relevant to its chiral recognition mechanism in HPLC
    • Yamamoto C, Yashima E, Okamoto Y (2002) Structural analysis of amylose tris (3, 5-dimethylphenylcarbamate) by NMR relevant to its chiral recognition mechanism in HPLC. J Am Chem Soc 124:12583-12589
    • (2002) J Am Chem Soc , vol.124 , pp. 12583-12589
    • Yamamoto, C.1    Yashima, E.2    Okamoto, Y.3
  • 29
    • 0001854516 scopus 로고
    • An NMR study of chiral recognition relevant to the liquid chromatographic separation of enantiomers by a cellulose derivative
    • Yashima E, Yamada M, Okamoto Y (1994) An NMR study of chiral recognition relevant to the liquid chromatographic separation of enantiomers by a cellulose derivative. Chem Lett 23:579-582
    • (1994) Chem Lett , vol.23 , pp. 579-582
    • Yashima, E.1    Yamada, M.2    Okamoto, Y.3
  • 30
    • 0030878392 scopus 로고    scopus 로고
    • Chromatographic enantioseparation and chiral discrimination in NMR by trisphenylcarbamate derivatives of cellulose, amylose, oligosaccharides, and cyclodextrins
    • Yashima E, Yamada M, Yamamoto C, Nakashima M, Okamoto Y (1997) Chromatographic enantioseparation and chiral discrimination in NMR by trisphenylcarbamate derivatives of cellulose, amylose, oligosaccharides, and cyclodextrins. Enantiomer 2:225-240
    • (1997) Enantiomer , vol.2 , pp. 225-240
    • Yashima, E.1    Yamada, M.2    Yamamoto, C.3    Nakashima, M.4    Okamoto, Y.5
  • 31
    • 0031534390 scopus 로고    scopus 로고
    • NMR studies of chiral discrimination by phenylcarbamate derivatives of cellulose
    • Okamoto Y, Yashima E, Yamamoto C (1997) NMR studies of chiral discrimination by phenylcarbamate derivatives of cellulose. Macromol Symp 120:127-137
    • (1997) Macromol Symp , vol.120 , pp. 127-137
    • Okamoto, Y.1    Yashima, E.2    Yamamoto, C.3
  • 32
    • 0029949417 scopus 로고    scopus 로고
    • NMR studies of chiral discrimination relevant to the liquid chromatographic enantioseparation by a cellulose phenylcarbamate derivative
    • Yashima E, Yamamoto C, Okamoto Y (1996) NMR studies of chiral discrimination relevant to the liquid chromatographic enantioseparation by a cellulose phenylcarbamate derivative. J Am Chem Soc 118:4036-4048
    • (1996) J Am Chem Soc , vol.118 , pp. 4036-4048
    • Yashima, E.1    Yamamoto, C.2    Okamoto, Y.3
  • 33
    • 0036249964 scopus 로고    scopus 로고
    • Chromatographic enantioseparation by cycloalkylcarbamate derivatives of cellulose and amylase
    • Kubota T, Yamamoto C, Okamoto Y (2002) Chromatographic enantioseparation by cycloalkylcarbamate derivatives of cellulose and amylase. Chirality 14:372-376
    • (2002) Chirality , vol.14 , pp. 372-376
    • Kubota, T.1    Yamamoto, C.2    Okamoto, Y.3
  • 34
    • 33847068319 scopus 로고    scopus 로고
    • NMR and computational studies of chiral discrimination by amylose tris(3, 5-dimethylphenylcarbamate)
    • Ye YK, Bai S, Vyas S, Wirth MJ (2007) NMR and computational studies of chiral discrimination by amylose tris(3, 5-dimethylphenylcarbamate). J Phys Chem B 111:1189-1198
    • (2007) J Phys Chem B , vol.111 , pp. 1189-1198
    • Ye, Y.K.1    Bai, S.2    Vyas, S.3    Wirth, M.J.4
  • 36
    • 0028901707 scopus 로고
    • Theoretical studies of type II-V chiral stationary phases
    • Lipkowitz KB (1995) Theoretical studies of type II-V chiral stationary phases. J Chromatogr A 694:15-37
    • (1995) J Chromatogr A , vol.694 , pp. 15-37
    • Lipkowitz, K.B.1
  • 37
    • 0035847244 scopus 로고    scopus 로고
    • Atomistic modeling of enantioselection in chromatography
    • Lipkowitz KB (2001) Atomistic modeling of enantioselection in chromatography. J Chromatogr A 906:417-442
    • (2001) J Chromatogr A , vol.906 , pp. 417-442
    • Lipkowitz, K.B.1
  • 38
    • 0028947992 scopus 로고
    • Computational studies on chiral discrimination mechanism of cellulose trisphenylcarbamate
    • Yashima E, Yamada M, Kaida Y, Okamoto Y (1995) Computational studies on chiral discrimination mechanism of cellulose trisphenylcarbamate. J Chromatogr A 694:347-354
    • (1995) J Chromatogr A , vol.694 , pp. 347-354
    • Yashima, E.1    Yamada, M.2    Kaida, Y.3    Okamoto, Y.4
  • 39
    • 0000821714 scopus 로고
    • Detailed molecular structure of a vinyl polymer glass
    • Theodorou DN, Suter UW (1985) Detailed molecular structure of a vinyl polymer glass. Macromolecules 18:1467-1478
    • (1985) Macromolecules , vol.18 , pp. 1467-1478
    • Theodorou, D.N.1    Suter, U.W.2
  • 40
    • 0036405383 scopus 로고    scopus 로고
    • Molecularmodeling of enantiomeric resolution of methylphenidate on cellulose tris benzoate chiral stationary phase
    • Aboul-Enein HY, Ali I, Laguerre M, Felix G (2002) Molecularmodeling of enantiomeric resolution of methylphenidate on cellulose tris benzoate chiral stationary phase. J Liq Chromatogr Relat Technol 25:2739-2748
    • (2002) J Liq Chromatogr Relat Technol , vol.25 , pp. 2739-2748
    • Aboul-Enein, H.Y.1    Ali, I.2    Laguerre, M.3    Felix, G.4
  • 42
    • 34249887364 scopus 로고    scopus 로고
    • Effects of backbone and side chain on the molecular environments of chiral cavities in polysaccharide-based biopolymers
    • Kasat RB, Wang NHL, Franses EI (2007) Effects of backbone and side chain on the molecular environments of chiral cavities in polysaccharide-based biopolymers. Biomacromolecules 8:1676-1685
    • (2007) Biomacromolecules , vol.8 , pp. 1676-1685
    • Kasat, R.B.1    Wang, N.H.L.2    Franses, E.I.3
  • 43
    • 33746906277 scopus 로고    scopus 로고
    • Direct probing of sorbent-solvent interactions for amylose tris(3, 5-dimethylphenylcarbamate) using infrared spectroscopy, X-ray diffraction, solid-state NMR, and DFT modeling
    • Kasat RB, Zvinevich Y, Hillhouse HW, Thomson KT, Wang NHL, Franses EI (2006) Direct probing of sorbent-solvent interactions for amylose tris(3, 5-dimethylphenylcarbamate) using infrared spectroscopy, X-ray diffraction, solid-state NMR, and DFT modeling. J Phys Chem B 110:14114-14122
    • (2006) J Phys Chem B , vol.110 , pp. 14114-14122
    • Kasat, R.B.1    Zvinevich, Y.2    Hillhouse, H.W.3    Thomson, K.T.4    Wang, N.H.L.5    Franses, E.I.6
  • 44
    • 33845383783 scopus 로고    scopus 로고
    • Interpretation of chromatographic retentions of simple solutes with an amylose-based sorbent using infrared spectroscopy and DFT modeling
    • Kasat RB, Chin CY, Thomson KT, Franses EI, Wang NHL (2006) Interpretation of chromatographic retentions of simple solutes with an amylose-based sorbent using infrared spectroscopy and DFT modeling. Adsorption 12:405-416
    • (2006) Adsorption , vol.12 , pp. 405-416
    • Kasat, R.B.1    Chin, C.Y.2    Thomson, K.T.3    Franses, E.I.4    Nhl, W.5
  • 45
    • 42149186311 scopus 로고    scopus 로고
    • Experimental probing and modeling of key sorbentsolute interactions of norephedrine enantiomers with polysaccharide-based chiral stationary phases
    • Kasat RB, Wang NHL, Franses EI (2008) Experimental probing and modeling of key sorbentsolute interactions of norephedrine enantiomers with polysaccharide-based chiral stationary phases. J Chromatogr A 1190:110-119
    • (2008) J Chromatogr A , vol.1190 , pp. 110-119
    • Kasat, R.B.1    Wang, N.H.L.2    Franses, E.I.3
  • 46
    • 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 RM (2003) Effects of alcohol mobile-phase modifiers on the structure and chiral selectivity of amylose tris(3, 5- dimethylphenylcarbamate) chiral stationary phase. J Chromatogr A 1015:99-110
    • (2003) J Chromatogr A , vol.1015 , pp. 99-110
    • Wang, T.1    Wenslow, R.M.2
  • 47
    • 14944373055 scopus 로고    scopus 로고
    • Selectivity of amylose tris(3, 5-dimethylphenylcarbamate) chiral stationary phase as a function of its structure altered by changing concentration of ethanol or 2-propanol mobile-phase modifier
    • Helmy R, Wang T (2005) Selectivity of amylose tris(3, 5-dimethylphenylcarbamate) chiral stationary phase as a function of its structure altered by changing concentration of ethanol or 2-propanol mobile-phase modifier. J Sep Sci 28:189-192
    • (2005) J Sep Sci , vol.28 , pp. 189-192
    • Helmy, R.1    Wang, T.2
  • 48
    • 53649085863 scopus 로고    scopus 로고
    • Vibrational circular dichroism of amylose carbamate: Structure and solvent-induced conformational changes
    • Ma SL, Shen S, Lee H, Yee N, Senanayake C, Nafie LA, Grinberg N (2008) Vibrational circular dichroism of amylose carbamate: structure and solvent-induced conformational changes. Tetrahedron Asymmetry 19:2111-2114
    • (2008) Tetrahedron Asymmetry , vol.19 , pp. 2111-2114
    • Ma, S.L.1    Shen, S.2    Lee, H.3    Yee, N.4    Senanayake, C.5    Nafie, L.A.6    Grinberg, N.7


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