Synlett
DOI: 10.1055/s-0036-1590884
letter
© Georg Thieme Verlag Stuttgart · New York

New Triazole-Containing Branched Bis(dipeptidomimetic) – Switching from Self-Dimerization to Anion-Binding Properties

Tin-Ki Chui, Hak-Fun Chow*
  • Department of Chemistry and Institute of Molecular Functional Materials, The Chinese University of Hong Kong, Shatin, NT, Hong Kong SAR   Email: hfchow@cuhk.edu.hk
This work is supported by the UGC of HK (project no: AoE/P-03/08). The 700 MHz NMR spectrometer was funded by the UGC of HKSAR (SEG/CUHK09).
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Publication History

Received: 30 June 2017

Accepted after revision: 28 July 2017

Publication Date:
25 August 2017 (eFirst)

Dedicated to Professor Victor Snieckus on the occasion of his 80th birthday

Abstract

A triazole-containing branched bis(dipeptidomimetic) 2 using l-lysine as a flexible branching unit was synthesized and characterized. The compound was found to form weak dimers (K dim = 19 M–1) in chloroform as shown by vapor pressure osmometry (VPO) and concentration-dependent 1H NMR studies. On the other hand, the compound was capable of binding chloride and monobasic diethyl phosphate (DEP) in chloroform. Job plot analysis, MALDI-TOF mass spectrometry, and NMR titration studies revealed a 1:1 binding stoichiometry with good binding affinities (K a ≈ 640–780 M–1). Structural studies using ­ROESY NMR spectroscopy and molecular modelling on the 2–DEP complex indicated the adoption of a helix-like conformation by the host with the guest situated near the branching juncture.

Supporting Information