Enantiomeric Recognition of d- and l-Amino Acid Methyl Ester Hydrochlorides by New Chiral Bis-pyridino-18-crown-6 Substituted with Urea, and Diphenyl Groups

  • Jae-Kon Kim
  • Jaehong Kim
  • Suhee Song
  • Ok-Sang Jung
  • Hongsuk Suh


The article reports the synthesis and chiral recognition properties of a new chiral bis-pyridino-18-crown-6 (7), having urea, diphenyl, and allyloxy groups. The chiral bis-pyridino-18-crown-6 was prepared by a thirteen-steps procedure from the commercially available (S)-(+)-mandelic acid and chelidamic acid. The association constants (K a) (1.33 × 103–3.20 × 103) for enantiomeric recognition of d- and l-amino acid methyl ester hydrochlorides using the chiral bis-pyridino-18-crown-6 have been examined by 1H-NMR titration method in CDCl3 at 25 °C. The chiral bis-pyridino-18-crown-6 showed higher association constants for the d-series amino acid methyl ester (d-AlaOMe, d-LeuOMe, d-MetOMe) hydrochlorides as compared to the corresponding l-series (l-AlaOMe, l-LeuOMe, l-MetOMe) hydrochlorides.


chiral crown ether chiral molecular recognition enantiomeric recognition host-guest hydrogen bonding 


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This work was supported by the Ministry of Information & Communications, Korea, under the Information Technology Research Center (ITRC) Support Program.


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Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • Jae-Kon Kim
    • 1
  • Jaehong Kim
    • 1
  • Suhee Song
    • 1
  • Ok-Sang Jung
    • 1
  • Hongsuk Suh
    • 1
  1. 1.Department of Chemistry and Center for Plastic Information SystemPusan National UniversityGeumjeong-Gu, BusanKorea

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