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

Author:

Chui Tin-Ki1,Chow Hak-Fun1ORCID

Affiliation:

1. Department of Chemistry and Institute of Molecular Functional Materials, The Chinese University of Hong Kong

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.

Funder

University Grants Committee

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

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