Publications associées à Cysteine-Cysteine Cross-Conjugation of both Peptides and Proteins with a Bifunctional Hypervalent Iodine-Electrophilic Reagent

Publications associées (17)

Engineering a synthetic signaling network in dendritic cells to improve anti-tumoral immunity

Effective induction of anti-tumor immunity requires dendritic cells (DCs) to internalize, process and present tumor antigens to T cells. However, the hostile tumor microenvironment (TME) impedes this process by suppressing DC maturation and antigen present ...

EPFL2024

Antibodies expand the scope of angiotensin receptor pharmacology

Shuhao Zhang, Patrick Daniel Barth

G-protein-coupled receptors (GPCRs) are key regulators of human physiology and are the targets of many small-molecule research compounds and therapeutic drugs. While most of these ligands bind to their target GPCR with high affinity, selectivity is often l ...

2024

Site-selective template-directed synthesis of antibody Fc conjugates with concomitant ligand release

Natalia Gasilova, Jean-Manuel Segura

Template-directed methods are emerging as some of the most effective means to conjugate payloads at selective sites of monoclonal antibodies (mAbs). We have previously reported a method based on an engineered Fc-III reactive peptide to conjugate a radionuc ...

Royal Soc Chemistry2023

High-affinity peptides developed against calprotectin and their application as synthetic ligands in diagnostic assays

Christian Heinis, Florence Pojer, Kelvin Ka Ching Lau, Cristina Diaz Perlas, Lluc Farrera Soler

A peptide was developed that binds to calprotectin, a marker of major inflammatory disorders, and found to be suited for diagnostic tests. The use of synthetic peptides in assays is of great interest due to their high precision, robustness and low price. ...

Nature Portfolio2023

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

Synthetic methodologies for C-C and C-N bond formation involving alkyl radicals

Guido Barzanò

C-C and C-N bonds are some of the most common structures in molecules ranging from drugs to catalysts and to food additives. Many coupling reactions were developed to form these types of bonds with excellent selectivity and good performance. Still, the syn ...

EPFL2020

"Doubly Orthogonal" Labeling of Peptides and Proteins

Jérôme Waser, Beat Fierz, Nora Guidotti, Raphaël Michel Henri Simonet-Davin, Romain Gaëtan Tessier, Javier De Ceballos Cerrajeria

Herein, we report a cysteine bioconjugation methodology for the introduction of hypervalent iodine compounds onto biomolecules. Ethynylbenziodoxolones (EBXs) engage thiols in small organic molecules and cysteine-containing peptides and proteins in a fast a ...

2019

Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers

Jérôme Waser, Matthew Wodrich, Paola Caramenti, Nina Declas, Romain Gaëtan Tessier

Enamides and enol ethers are valuable building blocks in synthetic chemistry, yet their stereoselective synthesis can be challenging. Herein, we report a new stereoselective synthesis of vinyl, aryl, alkynyl, alkyl and thio-substituted Z-enamides and enol ...

2019

Protein engineering approaches for direct antigen targeting in CD8+ T cell inducing vaccines

Vasiliki Panagiotou

Effective vaccine design and public vaccination programs have led to the eradication of several diseases and protected millions of people from deadly infections. However, intracellular infections remain a challenge and their eradication requires the activa ...

EPFL2016

Synthesis and structure-activity studies of well-defined nickel complexes as catalysts for cross coupling of alkyl electrophiles

Pablo Marcelo Perez Garcia

This dissertation is devoted to the development of well-defined nickel complexes as catalysts for cross coupling processes of alkyl electrophiles. In chapter one, we summarize recent cross coupling methodologies of alkyl electrophiles using nickel based ca ...

EPFL2015

Middle-down analysis of monoclonal antibodies with electron transfer dissociation Orbitrap FTMS

Yury Tsybin, Luca Fornelli, Daniel Ayoub

The rapid growth of approved biotherapeutics, e.g., monoclonal antibodies or immunoglobulins G (IgGs), demands improved techniques for their quality control. Traditionally, proteolysis-based bottom-up mass spectrometry (MS) has been employed. However, the ...

Amer Chemical Soc2014

Engineering antigens for in situ erythrocyte binding induces T-cell deletion

Jeffrey Alan Hubbell

Antigens derived from apoptotic cell debris can drive clonal T-cell deletion or anergy, and antigens chemically coupled ex vivo to apoptotic cell surfaces have been shown correspondingly to induce tolerance on infusion. Reasoning that a large number of ery ...

Natl Acad Sciences2013

Immune Engineering Via Differential Antigen Carriers and Co-Stimulatory Molecules

There is an increasing clinical need for vaccines capable of enhancing antigen-specific immune responses and treatments that can induce immunological tolerance toward a single antigen. Here we explore two platforms to enhance either immunization or toleriz ...

EPFL2012

A Well-Defined Ni Pincer Catalyst for Cross Coupling of Non-Activated Alkyl Halides and Direct C-H Alkylation

Oleg Vechorkin

Carbon-carbon bond forming reactions are among the most important and useful methods for organic synthesis. During the last years, significant progress has been made in this field. Whereas many catalysts were developed for the coupling of aryl, alkenyl, an ...

EPFL2011

Strategies to prolong the plasma residence time of peptide drugs

Christian Heinis, Lisa Pollaro

Peptides are an attractive class of molecules for the development of therapeutics because they combine unique properties such as high binding affinity, excellent target specificity, low toxicity and a relatively small mass. However, the short in vivo half- ...

2010

New developments in iron-catalyzed carbon-carbon bond forming reactions

The goal of this thesis is to develop new carbon-carbon bond forming reactions using inexpensive and simple coupling partners like aryl halides (pseudohalides), sulfonyl derivatives, Grignard reagents, alkenes and alkynes with metal catalysis, preferably u ...

EPFL2009

Anti-cooperativity in diffusion-controlled reactions with pairs of anisotropic domains: a model for the antigen-antibody encounter

Paolo De Los Rios, Francesco Piazza

The encounter between anisotropic agents in diffusion-controlled reactions is a topic of very general relevance in chemistry and biology. Here we introduce a simplified model of encounter of an isotropic molecule with a pair of partially reacting agents an ...

Springer-Verlag2005