Use of electrostatic interaction for chiral recognition. Enantioselective complexation of anionic binaphthyls with protonated amino-beta-cyclodextrin

被引:20
作者
Kano, K
Kitae, T
Takashima, H
机构
[1] Dept. of Molec. Sci. and Technology, Faculty of Engineering, Doshisha University, Tanabe
来源
JOURNAL OF INCLUSION PHENOMENA AND MOLECULAR RECOGNITION IN CHEMISTRY | 1996年 / 25卷 / 1-3期
关键词
D O I
10.1007/BF01041578
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The studies using NMR and capillary zone electrophoresis clearly reveal that protonated 6(A)-amino-6(A)-deoxy-beta-cyclodextrin recognizes the chirality of anionic binaphthyl derivatives such as 1,1'-binaphthyl-2,2'-diyl phosphate and 1,1'-binaphthyl-2,2'-dicarboxylate through electrostatic interaction between the host and the guest and simultaneous inclusion.
引用
收藏
页码:243 / 248
页数:6
相关论文
共 11 条
  • [1] THEORETICAL CONSIDERATIONS CONCERNING THE SEPARATION OF ENANTIOMERIC SOLUTES BY LIQUID-CHROMATOGRAPHY
    BOEHM, RE
    MARTIRE, DE
    ARMSTRONG, DW
    [J]. ANALYTICAL CHEMISTRY, 1988, 60 (06) : 522 - 528
  • [2] SUBSTITUENT EFFECTS AND CHIRAL DISCRIMINATION IN THE COMPLEXATION OF BENZOIC, 4-METHYLBENZOIC AND (RS)-2-PHENYLPROPANOIC ACIDS AND THEIR CONJUGATE BASES BY BETA-CYCLODEXTRIN AND 6(A)-AMINO-6(A)-DEOXY-BETA-CYCLODEXTRIN IN AQUEOUS-SOLUTION - POTENTIOMETRIC TITRATION AND H-1 NUCLEAR-MAGNETIC-RESONANCE SPECTROSCOPIC STUDY
    BROWN, SE
    COATES, JH
    DUCKWORTH, PA
    LINCOLN, SF
    EASTON, CJ
    MAY, BL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1993, 89 (07): : 1035 - 1040
  • [3] CYCLODEXTRIN-CATALYZED HYDROLYSIS OF OXAZOL-5(4H)-ONES - ENANTIOSELECTIVITY OF THE ACID-BASE AND RING-OPENING REACTIONS
    DAFFE, V
    FASTREZ, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1983, (06): : 789 - 796
  • [4] CONFORMATIONAL ENANTIOMERISM OF BILIRUBIN AND PAMOIC ACID-INDUCED BY PROTONATED AMINOCYCLODEXTRINS
    KANO, K
    ARIMOTO, S
    ISHIMURA, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1995, (08): : 1661 - 1666
  • [5] ABILITY OF NONCYCLIC OLIGOSACCHARIDES TO FORM MOLECULAR-COMPLEXES AND ITS USE FOR CHIRAL SEPARATION BY CAPILLARY ZONE ELECTROPHORESIS
    KANO, K
    MINAMI, K
    HORIGUCHI, K
    ISHIMURA, T
    KODERA, M
    [J]. JOURNAL OF CHROMATOGRAPHY A, 1995, 694 (01) : 307 - 313
  • [6] Kano K., 1993, BIOORGANIC CHEM FRON, V3, P1
  • [7] KANO K, 1993, SUPRAMOL CHEM, V2, P137
  • [8] Li S.F. Y., 1992, Capillary Electrophoresis
  • [9] SYNTHESIS OF MONOSUBSTITUTED CYCLOHEXAAMYLOSES
    MELTON, LD
    SLESSOR, KN
    [J]. CARBOHYDRATE RESEARCH, 1971, 18 (01) : 29 - +
  • [10] USE OF CHARGED AND NEUTRAL CYCLODEXTRINS IN CAPILLARY ZONE ELECTROPHORESIS - ENANTIOMERIC RESOLUTION OF SOME 2-HYDROXY ACIDS
    NARDI, A
    ELISEEV, A
    BOCEK, P
    FANALI, S
    [J]. JOURNAL OF CHROMATOGRAPHY, 1993, 638 (02): : 247 - 253