Photocontrolled chignolin-derived β-hairpin peptidomimetics

Podewin, Tom; Rampp, Michael S.; Turkanovic, I.; Karaghiosoff, Konstantin; Hoffmann‐Röder, Anja

doi:10.1039/c4cc10304a

Cited by 18 publications

(25 citation statements)

References 32 publications

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“…An azobenzene was chosen for incorporation into the peptide backbone of gramicidin S as it is known to give rise to a significant geometric change, high photoisomerization yield and fast isomerization, while being relatively easy to synthesise . In addition, an azobenzene in its cis conformation is known to mimic the β‐turn in β‐hairpin structures . We anticipated that a suitable azobenzene in its cis conformation would mimic the β‐turn of native gramicidin S, allowing the new peptide to adopt a β‐sheet structure.…”

Section: Introductionsupporting

confidence: 92%

Photopharmacological Control of Cyclic Antimicrobial Peptides

Yeoh

Polyak

et al. 2018

ChemBioChem

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Gramicidin S is a naturally occurring antimicrobial cyclic peptide. Herein, we present a series of cyclic peptides based on gramicidin S that contain an azobenzene photoswitch to reversibly control secondary structure and, hence, antimicrobial activity. 1H NMR spectroscopy and density functional theory calculations revealed a β‐sheet/β‐turn secondary structure for the cis configuration of each peptide, and an ill‐defined conformation for all associated trans structures. The cis‐enriched and trans‐enriched photostationary states (PSSs) for peptides 1–3 were assayed against Staphylococcus aureus to reveal a clear relationship between well‐defined secondary structure, amphiphilicity and optimal antimicrobial activity. Most notably, peptides 2 a and 2 b exhibited a fourfold difference in antimicrobial activity in the cis‐enriched PSS over the trans‐enriched equivalent. This photopharmacological approach allows antimicrobial activity to be regulated through photochemical control of the azobenzene photoswitch, thereby opening new avenues in the design and synthesis of future antibiotics.

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Section: Introductionsupporting

confidence: 92%

Photopharmacological Control of Cyclic Antimicrobial Peptides

Yeoh

Polyak

et al. 2018

ChemBioChem

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“…As previously observed in helices, the introduction of an azo group can modify specific peptide properties (section 4.3). Thus, the turn of the β-hairpin decapeptide known as chignolin [32,76,201] has been replaced by an azo group to achieve a photo-switchable peptide, which forms a β-hairpin when the azo group is cis conformation and is disordered if the azo is trans [298].…”

Section: Applicability Of β-Hairpin Peptidesmentioning

confidence: 99%

Design and structural characterisation of monomeric water-soluble α-helix and β-hairpin peptides: State-of-the-art

Morales

Jiménez

2019

Archives of Biochemistry and Biophysics

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Highlights α-helix and β-hairpin peptides are models for protein folding and stability Guidelines to design stable α-helical and β-hairpin-forming peptides are available Peptide structures are characterised by spectroscopic techniques, mainly CD and NMR Peptide structures are modulated and even modified by the environment Current peptide design aims to get improved bioactivity or novel biomaterials

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“…Although many examples of controlling the structure of b-hairpins [79][80][81][82][83][84][85][86] and cyclic peptides [87][88][89][90][91][92][93][94] are known, light is most frequently used to control protein-protein interactions by influencing the conformation of tethering loops or a-helices or by influencing the interactions of subunits (Fig. 24).…”

Section: Control Of Protein-protein Interactionsmentioning

confidence: 99%

Azobenzene photocontrol of peptides and proteins

2016

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The last few years have witnessed significant advances in the use of light as a stimulus to control biomolecular interactions. Great efforts have been devoted to the development of genetically encoded optobiological and small photochromic switches. Newly discovered small molecules now allow researchers to build molecular systems that are sensitive to a wider range of wavelengths of light than ever before with improved switching fidelities and increased lifetimes of the photoactivated states. Because these molecules are relatively small and adopt predictable conformations they are well suited as tools to interrogate cellular function in a spatially and temporally contolled fashion and for applications in photopharmacology.

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Photocontrolled chignolin-derived β-hairpin peptidomimetics

Cited by 18 publications

References 32 publications

Photopharmacological Control of Cyclic Antimicrobial Peptides

Photopharmacological Control of Cyclic Antimicrobial Peptides

Design and structural characterisation of monomeric water-soluble α-helix and β-hairpin peptides: State-of-the-art

Azobenzene photocontrol of peptides and proteins

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