constructing-thioethervinyl-sulfide-tethered-helical-peptides-via

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Here, we describe a detailed protocol for the preparation of thioether-tethered peptides using on-resin intramolecular/intermolecular thiol-ene ...

Peking University Shenzhen Graduate School

Different substitution groups on the in-tether chiral centre of chirality-induced helical peptides (CIH peptides) showed distinguishable effects on the peptides' cellular uptakes and binding affinities with the estrogen receptor α(ER-α). This study proves that in-tether chiral centres are a valuable modification site for constructing peptide ligands with preferable biophysical properties.

Switching substitution groups on the in-tether chiral centre influences backbone peptides' permeability and target binding affinity.

We have developed a general peptide macrocyclization strategy that involves a facile and chemoselective methionine bis-alkylation/dealkylation process. This method provides a straightforward and easy approach to generate cyclic peptides with tolerances of all amino acids (including Cys), variable loop sizes, and different linkers. The Met bis-alkylation we apply in this strategy yields two additional on-tether positive charges that could assist in the cellular uptake of the peptides. Notably, the bis-alkylated peptide could be reduced to release the original peptide both  and within cellular environments. This strategy provides an intriguing and facile traceless post-peptide-synthesis modification with enhanced cellular uptakes. Peptides constructed with this method could be utilized to zero in on various protein targets or to achieve other goals, such as drug delivery.

Article	Year
Switching substitution groups on the in-tether chiral centre influences backbone peptides' permeability and target binding affinity. Organic & biomolecular chemistry\| PubMed ID: 27929189	2017
Reversible stapling of unprotected peptides chemoselective methionine bis-alkylation/dealkylation. Chemical science\| PubMed ID: 29844896	2018

Xiaodong Shi

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