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Concept

Disulfure

Publications associées (30)

Methods for high-throughput synthesis and screening of peptide libraries

Zsolt Bognár

Macrocycles provide an attractive modality for drug development but the identification of ligands to targets of interest is hindered by the lack of large macrocyclic compound libraries for high-throughput screening. A strategy to efficiently synthesize lar ...

EPFL2024

Reactions of hypobromous acid with dimethyl selenide, dimethyl diselenide and other organic selenium compounds: kinetics and product formation

Urs von Gunten

Selenium (Se) is an essential micronutrient for many living organisms particularly due to its unique redox properties. We recently found that the sulfur (S) analog for dimethyl selenide (DMSe), i.e. dimethyl sulfide (DMS), reacts fast with the marine oxida ...

Royal Soc Chemistry2024

High-Density Immobilization of TCEP on Silica Beads for Efficient Disulfide Reduction and Thiol Alkylation in Peptides

Christian Heinis

Tris-(2-carboxyethyl)phosphine (TCEP) linked to agarose beads is widely used for reducing disulfide bridges in proteins and peptides. The immobilization of TCEP on beads allows efficient removal after reduction to prevent its reaction with alkylating reage ...

2023

Towards Uncovering the Mechanisms of Electrophile Sensing and Signaling

Chloé Rogg

Native reactive electrophile species (RES) such as 4-hydroxynonenal (HNE) act as cellular signals through covalent modification of kinetically-privileged electrophile sensor proteins. Research efforts in the field focus mainly on identifying these sensor p ...

EPFL2023

Development of methods for the synthesis of large combinatorial libraries of macrocyclic compounds

Mischa Schüttel

Macrocycles have raised much interest in the pharmaceutical industry due to their ability to bind challenging targets while often still being able to cross membranes to reach intracellular proteins. However, the development of macrocyclic ligands to new di ...

EPFL2023

Architecture-Controllable Single-Crystal Helical Self-assembly of Small-Molecule Disulfides with Dynamic Chirality

Lukas Pfeifer

Beyond the common supramolecular helical polymers in solutions, controlling single-crystal helical self-assembly with precisely defined chirality and architectures has been challenging. Here, we report that simply merging static homochiral amino acids with ...

AMER CHEMICAL SOC2023

A molecular device for the redox quality control of GroEL/ES substrates

Camille Véronique Bernadette Goemans

Hsp60 chaperonins and their Hsp10 cofactors assist protein folding in all living cells, constituting the paradigmatic example of molecular chaperones. Despite extensive investigations of their structure and mechanism, crucial questions regarding how these ...

2023

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

Christian Heinis, Alexander Lund Nielsen, Manuel Leonardo Merz, Ganesh Kumar Mothukuri, Zsolt Bognár, Peter Matei Frisius Pânzar

Thiol groups are suitable handles for site-selectively modifying, immobilizing or cyclizing individual peptides or entire peptide libraries. A limiting step in producing the thiol-functionalized peptides is the chromatographic purification, which is partic ...

2022

Taming the radical cation intermediate enabled one-step access to structurally diverse lignans

Jieping Zhu, Qiang Wang, Cédric Fung, Jia-Chen Xiang

Lignans, in spite of their structural diversity, are all biosynthetically derived from coniferyl alcohol. We report herein a divergent synthesis of lignans from biomass-derived monolignols in a short synthetic sequence. Blue LED irradiation of a dichlorome ...

Nature Research2022

Single-Chain Nanoparticles for Intracellular Drug Delivery

Suiyang Liao

Single-chain nanoparticles (SCNPs) are a type of polymeric nanoparticles formed by collapsing/folding individual polymer chains via intra-molecular interactions. Their emergence holds promise to construct sub-20 nm polymeric nanoparticles with defined stru ...

EPFL2022

Mechanical Reinforcement of Hydrogels through Physical Crosslinks and Double Network Granular Architecture

Alvaro Lino Boris Charlet

Throughout nature, organisms fabricate a myriad of materials to sustain their lifestyle. Many of the soft materials are composed of water-swollen networks of organic molecules, so-called hydrogels. They generally contribute to the mechanical integrity of t ...

EPFL2022

Methods for the generation of large combinatorial macrocycle libraries

Sevan Mleh Habeshian

Macrocycles are an attractive class of molecules due to their good binding properties and yet rather small size that allows, in many cases, crossing membranes to reach intracellular targets. In comparison to classical small molecule drugs, macrocycles are ...

EPFL2021

Cys-Cys and Cys-Lys Stapling of Unprotected Peptides Enabled by Hypervalent Iodine Reagents

Jérôme Waser, Christian Heinis, Elija Grinhagena, Gontran Sangouard, Javier De Ceballos Cerrajeria

Easy access to a wide range of structurally diverse stapled peptides is crucial for the development of inhibitors of protein-protein interactions. Herein, we report bis-functional hypervalent iodine reagents for two-component cysteine-cysteine and cysteine ...

Wiley-VCH Verlag GmbH2021

Bioluminescent compositions and uses thereof

Elena Goun, Pavlo Khodakivskyi, Aleksey Yevtodiyenko, Hacer Karatas, Manuel Simon Drefahl

Compositions and methods for non-invasively monitoring the intracellular processing of a biomolecule are provided. The compositions have a novel thio-luciferin moiety which can be conjugated to the biomolecule directly or via a linker such as disulfide bon ...

2021

Mechanical Activation of Chemical Bonds at Polymer Interfaces

Julian Nicolas Bleich

Polymer brushes are a specific class of polymer thin films in which each chain is tethered to the underlying substrate via one chain end. In sufficiently densely grafted assemblies, the individual polymer chains are forced into an extended chain conformati ...

EPFL2021

Interfacial Water Many-Body Effects Drive Structural Dynamics and Allosteric Interactions in SARS-CoV-2 Main Protease Dimerization Interface

Frédéric Célerse

Following our previous work (Chem. Sci. 2021, 12, 4889-4907), we study the structural dynamics of the SARS-CoV-2 Main Protease dimerization interface (apo dimer) by means of microsecond adaptive sampling molecular dynamics simulations (50 mu s) using the A ...

AMER CHEMICAL SOC2021

Method Development towards Orthogonal Electrophile Delivery

Lingxi Wang

Redox signaling events mediated by reactive electrophilic species (RES) are key players in several cellular processes. However, the studies on RES have been challenging due to their high reactivity towards numerous nucleophilic groups present in the cells ...

EPFL2021

Strain and filler ratio transitions from chains network to filler network damage in EPDM during single and cyclic loadings

Nicolas Candau, Oguzhan Oguz

Chains and filler network damage were investigated during single and multiple cycles on a series of vulcanized EPDM containing various filler contents. In both series of experiments, a strain and a filler ratio transitions for damage mechanisms were identi ...

2020

The Effect of Thiol Structure on Allyl Sulfide Photodegradable Hydrogels and their Application as a Degradable Scaffold for Organoid Passaging

Matthias Lütolf, Nikolche Gjorevski

Intestinal organoids are useful in vitro models for basic and translational studies aimed at understanding and treating disease. However, their routine culture relies on animal-derived matrices that limit translation to clinical applications. In fact, ther ...

Wiley-V C H Verlag Gmbh2020

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

Jérôme Waser, Marion Marie-Agnès Garreau, Stephanie Grace Elizabeth Amos, Luca Buzzetti

Organic dyes have emerged as a reliable class of photoredox catalysts. Their great structural variety combined with the easy finetuning of their electronic properties has unlocked new possibilities for the generation of reactive intermediates. In this revi ...

2020