Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and Anion Binding Affinities of Novel Molecular Tweezers Based on Chenodeoxycholic Acid Bearing Different Lengths of Arm

  • Kim, Ki-Soo (Department of Applied Chemistry, Kyungpook National University) ;
  • Jang, Hyun-Seok (Department of Applied Chemistry, Kyungpook National University) ;
  • Kim, Hong-Seok (Department of Applied Chemistry, Kyungpook National University)
  • Published : 2006.09.20
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Abstract

Molecular tweezers based on chenodeoxycholic acid bearing different lengths of arm were synthesized andtheir anion binding affinities were evaluated by $^1H$ NMR, isothermal calorimetric titration, and ESI mass spectrometry. Molecular tweezer 6 showed a high selectivity toward $H_2PO_4\;^-$ over $Cl^-,\;Br^-,\;I^-, $ and $CH_3CO_2\;^-$ by $^1H$ NMR titration, whereas the association constant for $F^-$ revealed the largest value as determined by ITC. The selectivity of 6 towards $F^-$ was about 103 times higher than that of $Cl^-,\;H_2PO_4\;^- $, and $CH_3CO_2\;^-$. ITCexperiment of 6 with $F^-$ in a DMSO showed two binding modes; two sequential association constants $K_1\;=\;2.77\;{\times}\;10^5\;M^{-1}$ and $K_2\;=\;8.68\;{\times}\;10^6\;M^{-1}$ were found. These sequential bindings were confirmed by ESI massspectrometry. 1 : 1 and 1 : 2 complexes of 6 and $F^-$ were found at m/z 868.08 and 884.04.

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