β-Hairpin Stabilization Through an Interstrand Triazole Bridge

Overview

Journal Chem Commun (Camb)

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2011 Dec 3

PMID 22134485

Citations 6

Authors

Veronica Celentano

Donatella Diana

Lucia De Rosa

Alessandra Romanelli

Roberto Fattorusso

Luca Domenico DAndrea

Affiliations

Soon will be listed here.

Abstract

β-Hairpin peptides were conformationally stabilized through a 1,4 disubstituted 1,2,3-triazole interstrand linkage. A NMR conformational analysis revealed that the β-hairpin content depends on the number and position of substituent methylene units of the 1,2,3-triazole ring. These results will allow the design of metabolically stable peptidomimetic analogs of bioactive β-hairpin peptides.

Citing Articles

Structure-Based Design of Peptides Targeting VEGF/VEGFRs.

Di Stasi R, De Rosa L, DAndrea L Pharmaceuticals (Basel). 2023; 16(6).

PMID: 37375798 PMC: 10302803. DOI: 10.3390/ph16060851.

Bent Into Shape: Folded Peptides to Mimic Protein Structure and Modulate Protein Function.

Merritt H, Sawyer N, Arora P Pept Sci (Hoboken). 2021; 112(1).

PMID: 33575525 PMC: 7875438. DOI: 10.1002/pep2.24145.

Hydrogen Bond Surrogate Stabilization of β-Hairpins.

Sawyer N, Arora P ACS Chem Biol. 2018; 13(8):2027-2032.

PMID: 30005156 PMC: 7187762. DOI: 10.1021/acschembio.8b00641.

1,2,3-Triazole Rings as a Disulfide Bond Mimetic in Chimeric AGRP-Melanocortin Peptides: Design, Synthesis, and Functional Characterization.

Tala S, Singh A, Lensing C, Schnell S, Freeman K, Rocca J ACS Chem Neurosci. 2017; 9(5):1001-1013.

PMID: 29257879 PMC: 5955799. DOI: 10.1021/acschemneuro.7b00422.

Structure-Based Design of Inhibitors of Protein-Protein Interactions: Mimicking Peptide Binding Epitopes.

Pelay-Gimeno M, Glas A, Koch O, Grossmann T Angew Chem Int Ed Engl. 2015; 54(31):8896-927.

PMID: 26119925 PMC: 4557054. DOI: 10.1002/anie.201412070.