New C2-symmetric 2,2′-bipyridine crown macrocycles for enantioselective recognition of amino acid derivatives

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review

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Author(s)

  • Chi-Sing Lee
  • Pang-Fei Teng
  • Wing-Leung Wong
  • Hoi-Lun Kwong
  • Albert S. C. Chan

Detail(s)

Original languageEnglish
Pages (from-to)7924-7930
Journal / PublicationTetrahedron
Volume61
Issue number33
Publication statusPublished - 15 Aug 2005

Abstract

A series of new C2-symmetric 2,2′-bipyridine-contaning crown macrocycles 1-4 has been developed for enantiomeric recognition of amino acid derivatives. These new macrocycles have been showed to be strong complexing agents for primary organic ammonium salts (with K up to 4.83×10 5 M-1 and -ΔG0 up to 32.4 kJ mol -1) and also useful chromophores for UV-vis titration studies. These macrocyclic hosts exhibited enantioselective binding towards the (S)-enantiomer of phenylglycine methyl ester hydrochloride (Am1) with K(S)/K (R) up to 2.10 (ΔΔG0=-1.84 kJ mol -1) in CH2Cl2 with 0.25% CH3OH. The structure-binding relationship studies showed that the aromatic subunit and the ester group of the ammonium guests are both important for good enantioselectivity. In addition, the host-guest complexes have been studied using various NMR experiments. © 2005 Elsevier Ltd. All rights reserved.

Research Area(s)

  • Amino acid derivatives, Enantioselectivity, Macrocyclic hosts

Citation Format(s)

New C2-symmetric 2,2′-bipyridine crown macrocycles for enantioselective recognition of amino acid derivatives. / Lee, Chi-Sing; Teng, Pang-Fei; Wong, Wing-Leung et al.
In: Tetrahedron, Vol. 61, No. 33, 15.08.2005, p. 7924-7930.

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review