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Anion Binding Affinities of Linear Penta- homopeptides in Solution

In the recent past cyclic peptides have attracted an increasing interest due to their unique chemical and biological properties. These compounds generally exhibit improved metabolic stability and bioavailability as well as enhanced binding affinity and selectivity toward substrates compared to their more flexible linear analogs. In the synthesis of cyclic peptides, regardless of the macrocyclization strategy, the main factor that affects the success of a ring closure reaction is the conformational preorganization, that is the ability of a linear precursor to bring its reactive termini in the close spatial proximity. We have recently reported that not only cations but also chloride anion is able to act as directing agent for promoting the cyclization of linear peptides. In the scope of this work, we have tested the binding affinities of two linear peptides towards several anions in solution by means of microcalorimetric and 1H NMR titrations as well as classical molecular dynamics simulations. The results of these investigations could point to the new anion templating agents for the intramolecular head-tail linear peptide cyclization.

anion-binding ; homopeptides ; MD simulation ; NMR ; thermodynamics

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