Solid-phase peptide synthesis on disulfide-linker resin followed by reductive release affords pure thiol-functionalized peptides

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Hypervalent Iodine-Mediated Late-Stage Peptide and Protein Functionalization

Jérôme Waser, Elija Grinhagena, Emmanuelle Madeline Dominique Allouche

Hypervalent iodine compounds are powerful reagents for the development of novel transformations. As they exhibit low toxicity, high functional group tolerance, and stability in biocompatible media, they have been used for the functionalization of biomolecu ...

Wiley-VCH Verlag GmbH2022

Small peptide diversification through photoredox-catalyzed oxidative C-terminal modification

Jérôme Waser, Eliott Hugo Joran Le Du, Marion Marie-Agnès Garreau

A photoredox-catalyzed oxidative decarboxylative coupling of small peptides is reported, giving access to a variety of N,O-acetals. They were used as intermediates for the addition of phenols and indoles, leading to novel peptide scaffolds and bioconjugate ...

2021

Amphiphilic Iodine(III) Reagents for the Lipophilization of Peptides in Water

Jérôme Waser, Durga Prasada Rao Hari, Romain Gaëtan Tessier, Abhaya Kumar Mishra

We report the functionalization of cysteine residues with lipophilic alkynes bearing a silyl group or an alkyl chain using amphiphilic ethynylbenziodoxolone reagents (EBXs). The reactions were carried out in buffer (pH 6 to 9), without organic co-solvent o ...

Wiley-VCH Verlag GmbH2021

A minimalistic cyclic ice-binding peptide from phage display

Harm-Anton Klok, Luciano Andres Abriata, Matthew Gibson, Xudong Kong, Corey Alfred Stevens

Developing molecules that emulate the properties of naturally occurring ice-binding proteins (IBPs) is a daunting challenge. Rather than relying on the (limited) existing structure–property relationships that have been established for IBPs, here we report ...

Nature Research2021

Reversibly Cross-Linking Polymer Brushes Using Interchain Disulfide Bonds

Harm-Anton Klok, Piotr Mocny

The introduction of interchain cross-links in surface-grafted polymer brushes increases the robustness and mechanical properties of these thin polymer films. In most cases, cross-linked polymer brushes contain permanent interchain cross-links. The use of r ...

American Chemical Society2020

Development of Photocatalysts towards the Visible-Light driven C-Terminal Bioconjugation of Peptides and Proteins

Marion Marie-Agnès Garreau

If small molecules have led to tremendous progress in curing diseases, new therapeutic agents such as peptides or antibody-drugs conjugates have emerged as a highly promising next generation of pharmaceuticals. As for small molecules, their derivatization ...

EPFL2020

De novo development of proteolytically resistant therapeutic peptides for oral administration

Christian Heinis, Luciano Andres Abriata, Florence Pojer, Xudong Kong, Vanessa Carle, Kaycie Marie Butler, Jun Moriya

The oral administration of peptide drugs is hampered by their metabolic instability and limited intestinal uptake. Here, we describe a method for the generation of small target-specific peptides (less than 1,600 Da in size) that resist gastrointestinal pro ...

2020

Synthesis of DNA‐encoded disulfide‐ and thioether‐cyclized peptides

Christian Heinis, Van Manh Pham, Milan Bergeron-Brlek

DNA-encoded chemical library technologies enable the screening of large combinatorial libraries of chemically and structurally diverse molecules, including short cyclic peptides. A challenge in the combinatorial synthesis of cyclic peptides is the final st ...

2020

Crosslinking Allosteric Sites on the Nucleosome Core Particle

Lucinda Kate Batchelor

Designing compounds that bind to the acidic patch of the nucleosome core particle (NCP) is an emerging therapeutic approach that can inhibit the binding of key chromatin factors. Pretreatment of human ovarian carcinoma, A2780, cells with RAPTA-T, an antime ...

EPFL2019

Thiol-to-amine cyclization reaction enables screening of large libraries of macrocyclic compounds and the generation of sub-kilodalton ligands

Christian Heinis, Gerardo Turcatti, Julien Bortoli Chapalay, Xudong Kong, Van Manh Pham, Patrick Andreas Gonschorek, Jonathan Patrice Vesin, Sangram Shivdas Kale, Milan Bergeron-Brlek, João Miguel Franco Machado

Macrocyclic compounds are an attractive modality for drug development, but the limited availability of large, structurally diverse macrocyclic libraries hampers the discovery of leads. Here, we describe the discovery of efficient macrocyclization reactions ...

2019

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Thiol-to-amine cyclization reaction enables screening of large libraries of macrocyclic compounds and the generation of sub-kilodalton ligands

2019