Publications associées à Ethynylation of Cysteine Residues: From Peptides to Proteins in Vitro and in Living Cells

Novel Alkynylation Methods through the Combination of Hypervalent Iodine Reagents and Alkynyl-trifluoroborate Salts

The alkyne motif is a versatile functional group often encountered in organic chemistry. It can be involved in various transformations such as the alkyne-azide cycloaddition and has found widespread application in medicinal chemistry, chemical biology and ...

EPFL2024

Functionalization of harmonic nanoparticles for drug release and multimodal imaging applications

Adrian Stefan Gheata

Cancer is among the leading causes of death worldwide, and as knowledge of the disease continues to grow there is an increasing interest towards precision medicine: more specifically towards the theranostics field, i.e the development of targeted molecular ...

EPFL2024

Synthesis and application of bifunctional hypervalent iodine reagents for peptide modification

Elija Grinhagena

Protein-protein interactions (PPIs) are responsible for regulating many biological processes in human bodies. PPIs often have a large binding site and often interact through an alpha helical segment. Therefore, the inhibition of PPIs can be difficult using ...

EPFL2023

Terminal Alkynes as One-Carbon Donors in [5+1] Heteroannulation: Synthesis of Pyridines via Ynimine Intermediates and Application in the Total Synthesis of Anibamine B

Qian Wang, Jieping Zhu, Rémi Hugo Lavernhe

Transition-metal-catalyzed [4+2] heteroannulation of alpha,beta-unsaturated oximes and their derivatives with alkynes has been developed into a powerful strategy for the synthesis of pyridines. It nevertheless lacks regioselectivity when unsymmetrically su ...

Wiley-VCH Verlag GmbH2023

Synthesis and Applications of Ynimines and Enantioselective Total Synthesis of Artatrovirenol A

Rémi Hugo Lavernhe

The first chapter of this thesis describe the development of a general synthesis of ynimines, an under-exploited motif in organic chemistry. In the presence of an inexpensive copper catalyst and 2,2'-biquinoline, reaction of easily accessible O-acyloximes ...

EPFL2023

Carbon nanotube uptake in cyanobacteria for near-infrared imaging and enhanced bioelectricity generation in living photovoltaics

Vitalijs Zubkovs, Ardemis Anoush Boghossian, Alessandra Antonucci, Charlotte Elisabeth Marie Roullier, Nils Schürgers, Benjamin Paul Johanès Gabriel Lambert, Alice Judith Gillen, Melania Reggente, Mohammed Mouhib

Single-walled carbon nanotubes (SWCNTs) have unique optoelectronic properties that make them suitable for applications ranging from phototherapy to imaging and sensing, but their uptake has mainly been explored in eukaryotic cells. Here the authors explore ...

2022

Covalent and Noncovalent Conjugation of Degradable Polymer Nanoparticles to T Lymphocytes

Harm-Anton Klok, Tanja Thomsen

Cells are attractive as carriers that can help to enhance control over the biodistribution of polymer nanomedicines. One strategy to use cells as carriers is based on the cell surface immobilization of the nanoparticle cargo. While a range of strategies ca ...

American Chemical Society2021

Copper‐Catalyzed Aza‐Sonogashira Cross‐Coupling to Ynimines: Development and Application to the Synthesis of Heterocycles

Jieping Zhu, Qiang Wang, Rémi Hugo Lavernhe

Nitrogen substituted alkynes such as ynamines and ynamides are versatile synthetic building blocks in organic chemistry. Ynimines bearing additional nucleophilic and electrophilic centers relative to ynamines and ynamides are expected to have high syntheti ...

Wiley-VCH Verlag GmbH2021

Asymmetric azide-alkyne Huisgen cycloaddition on chiral metal surfaces

Harald Brune, Roland Widmer, Roland Hany, Michael Bauer, Samuel Thomas Stolz

Achieving fundamental understanding of enantioselective heterogeneous synthesis is marred by the permanent presence of multitudinous arrangements of catalytically active sites in real catalysts. In this study, we address this issue by using structurally co ...

NATURE RESEARCH2021

Development of remote C-H bond functionalization of redox-active alcohol derivatives and oxidative transformations under photoredox catalysis

Alexandre Julien Florent Leclair

The development of radical-based remote C(sp3)-H functionalizations of redox-active alcohol derivatives, oxidative cycloaddition and rearrangement transformations under visible light photocatalysis constitute the basis of this thesis. The first chapter des ...

EPFL2021

Visualizing intracellular nanostructures of living cells by nanoendoscopy-AFM

Marcos Penedo Garcia

Atomic force microscopy (AFM) is the only technique that allows label-free imaging of nanoscale biomolecular dynamics, playing a crucial role in solving biological questions that cannot be addressed by other major bioimaging tools (fluorescence or electron ...

AMER ASSOC ADVANCEMENT SCIENCE2021

Surface functionalization of metal oxide harmonic nanoparticles for targeted cancer imaging

Raphaël Jovita De Matos

Cancer is a major health burden worldwide and the leading cause of death in industrialized countries. Early detection is a primary factor of survival and remission rate. Classical imaging methods such as magnetic resonance imaging, ultrasound imaging and m ...

EPFL2020

Synthesis, Characterisation and Crystal structure of a New Cu(II)-carboxamide Complex and CuO nanoparticles as New Catalysts in the CuAAC reaction and Investigation of their Antibacterial activity

Kurt Schenk, Farzaneh Fadaei Tirani

The bidentate carboxamide ligand N-(thiazole-2-yl) picolinamide (LH) was synthesized in the environmentally friendly ionic liquid TBAB, and the five-coordinated Cu-II-complex, [Cu(L)(2)(H2O)]center dot CHCl3 (1) was synthesized from LH and copper(II)acetat ...

2020

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

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

Copper-Catalyzed 1,2-Methoxy Methoxycarbonylation of Alkenes with Methyl Formate and Synthetic Studies Towards the Total Synthesis of Koumine, Voacafricine A and Voacafricine B

Balázs Budai

The development of an unusual oxidative alkene difunctionalization using methyl formate and syn-thetic studies towards alkaloid natural products provide the basis of the thesis. The first chapter details the development of a method that forges methoxycarbo ...

EPFL2020

Fluorogenic probes for live-cell imaging

Aleksandar Salim

The development of novel fluorogenic probes and their use in live-cell imaging lead to a plethora of discoveries in biological research. Herein I report on novel red fluorogenic probes for live-cell super-resolution microscopy of various cellular organelle ...

EPFL2020

Application of Hypervalent Iodine Reagents for Novel Cysteine Labeling

Romain Gaëtan Tessier

Selective functionalization of peptides and proteins has always been a valuable tool for the study and manipulation of biological processes. In this context, cysteines are of particular interest. Their intrinsic high nucleophilicity makes these amino acids ...

EPFL2019

Nitrogen-doped graphene stabilized copper nanoparticles for Huisgen [3+2] cycloaddition "click" chemistry

Yves Leterrier, Véronique Michaud, Monika Srivastava, Sravendra Rana

Nitrogen-doped reduced graphene oxide (NRGO) stabilized copper nanoparticles are designed to assist Cu(I)-catalyzed Huisgen [3+2] cycloaddition "click" chemistry (CuAAC). This study demonstrates a robust route for the synthesis of vastly dispersed heteroge ...

Royal Society of Chemistry2019

Controlling topology, dynamics and function of polymer brushes via post-polymerization modification

Piotr Mocny

Polymer brushes are a class of thin coatings, where each of chains is tethered to the underlying substrate via one chain end. Densely grafted polymer brushes feature a stretched chain conformation, which in a unique way enhances their lubrication and non-b ...

EPFL2019