Chiral Discrimination by 4-Chloro- and 4-Bromophenylcarbamates of Maltooligosaccharides in HPLC, NMR, and CD

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Abstract

4-Chloro- and 4-bromophenylcarbamates of maltooligosaccharides (<i>n</i> = 5, 6, and 7) were prepared and their chiral recognition abilities as a chiral stationary phase for HPLC were evaluated. The maltooligosaccharides carbamates exhibited a characteristic chiral recognition depending on the racemates and resolved several racemates in HPLC. The enantioselectivity as well as elution order of enantiomers on the maltooligosaccharide derivatives were similar to those on the corresponding amylose phenylcarbamte derivatives. The maltooligosaccharides also showed chiral discrimination for some racemates in NMR; the proton resonances of racemates, such as <i>trans</i>-stilbene oxide, benzoin, and 1,2,2,2-tetraphenylethanol were split into a pair of peaks due to the enantiomers. A good correlation between the NMR results and the chromatographic elution order was observed for most racemates. An enantiomeric guest, bilirubin, was also chirally discriminated by the maltooligosaccharides in chloroform to show an induced CD. The structures of the maltohexaose derivatives were examined by molecular mechanics and molecular dynamics simulations.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 70(8), 1977-1984, 1997-08-15

    The Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008922207
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • NDL Article ID
    4277782
  • NDL Source Classification
    ZP1(科学技術--化学・化学工業)
  • NDL Call No.
    Z53-B35
  • Data Source
    CJP  NDL  J-STAGE 
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