Search results for "pseudopeptides"
showing 4 items of 4 documents
Oxoanion binding to a cyclic pseudopeptide containing 1,4-disubstituted 1,2,3-triazole moieties
2016
A macrocyclic pseudopeptide 3 is described featuring three amide groups and three 1,4-disubstituted 1,2,3-triazole units along the ring. This pseudopeptide was designed such that the amide NH groups and the triazole CH groups converge toward the cavity, thus creating an environment well suited for anion recognition. Conformational studies in solution combined with X-ray crystallography confirmed this preorganisation. Solubility of 3 restricted binding studies to organic media such as 5 vol% DMSO/acetone or DMSO/water mixtures with a water content up to 5 vol%. These binding studies demonstrated that 3 binds to a variety of inorganic anions in DMSO/acetone including chloride, nitrate, sulfat…
Bisferrocenyl-functionalized pseudopeptides: access to separated ionic and electronic contributions for electrochemical anion sensing
2016
Pseudopeptidic receptors containing ferrocene fragments have been prepared and their response to a series of anions was measured by a voltammetry of microparticles methodology. Such water-insoluble compounds yield anion-assisted reversible solid-state oxidations differing in their open-circuit potential and their midpeak potential recorded in cyclic voltammetric measurements. The difference between those potentials provides the individual thermodynamic contributions of electron and proton transfer, revealing that the mechanism of an ion-sensitive electrode can differ in potentiometry and voltammetry. The studied receptors are potentially interesting for potentiometric sensing, showing relat…
Efficient stabilisation of a dihydrogenphosphate tetramer and a dihydrogenpyrophosphate dimer by a cyclic pseudopeptide containing 1,4-disubstituted …
2017
A cyclic pseudooctapeptide 2 is described containing 1,4-disubstituted 1,2,3-triazole moieties. This compound features eight converging hydrogen bond donors along the ring, namely four amide NH and four triazole CH groups, which enable 2 to engage in interactions with anions. While fully deprotonated sulfate anions exhibit only moderate affinity for 2, protonated anions such as dihydrogenpyrophosphate and dihydrogenphosphate anions are strongly bound. Complexation of the phosphate-derived anions involves sandwiching of a dihydrogenpyrophosphate dimer or a dihydrogenphosphate tetramer between two pseudopeptide rings. X-ray crystallography provided structural information, while 1H NMR spectro…
Efficient stabilisation of a dihydrogenphosphate tetramer and a dihydrogenpyrophosphate dimer by a cyclic pseudopeptide containing 1,4-disubstituted …
2017
A cyclic pseudooctapeptide 2 is described containing 1,4-disubstituted 1,2,3-triazole moieties. This compound features eight converging hydrogen bond donors along the ring, namely four amide NH and four triazole CH groups, which enable 2 to engage in interactions with anions. While fully deprotonated sulfate anions exhibit only moderate affinity for 2, protonated anions such as dihydrogenpyrophosphate and dihydrogenphosphate anions are strongly bound. Complexation of the phosphate-derived anions involves sandwiching of a dihydrogenpyrophosphate dimer or a dihydrogenphosphate tetramer between two pseudopeptide rings. X-ray crystallography provided structural information, while 1 H NMR spectr…