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Hydrocarbon constrained peptides - understanding preorganisation and binding affinity. | LitMetric

AI Article Synopsis

Article Abstract

The development of constrained peptides represents an emerging strategy to generate peptide based probes and hits for drug-discovery that address challenging protein-protein interactions (PPIs). In this manuscript we report on the use of a novel α-alkenylglycine derived amino acid to synthesise hydrocarbon constrained BH3-family sequences (BIM and BID). Our biophysical and structural analyses illustrate that whilst the introduction of the constraint increases the population of the bioactive α-helical conformation of the peptide in solution, it does not enhance the inhibitory potency against pro-apoptotic Bcl-x and Mcl-1 PPIs. SPR analyses indicate binding occurs an induced fit mechanism whilst X-ray analyses illustrate none of the key interactions between the helix and protein are disturbed. The behaviour derives from enthalpy-entropy compensation which may be considered in terms of the ground state energies of the unbound constrained and unconstrained peptides; this has implications for the design of preorganised peptides to target protein-protein interactions.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5618334PMC
http://dx.doi.org/10.1039/c5sc04048eDOI Listing

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