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Concept

Hémiacétal

Publications associées (16)

Development of Sustainable Carbohydrate-Based Solvents by Acetal Functionalisation of Biomass

Anastasiia Komarova

Organic solvents are ubiquitous in industrial and domestic applications from the production of pharmaceuticals to household consumer products. The negative impact of most traditional solvents, especially aprotic types, on the environment, health, and safet ...

EPFL2024

Hypervalent Iodine: New Reagents and Functionalization of Peptides

Eliott Hugo Joran Le Du

Alkynes are found in a multitude of natural or synthetic bioactive compounds. In addition to the capacity of these chemical motifs to impact the physicochemical properties of a molecule of interest, the well-established reactivity of alkynes makes them ide ...

EPFL2023

Hydrogen Peroxide Formation during Ozonation of Olefins and Phenol: Mechanistic Insights from Oxygen Isotope Signatures

Urs von Gunten, Joanna Maria Houska

Mitigation of undesired byproducts from ozonation of dissolved organic matter (DOM) such as aldehydes and ketones is currently hampered by limited knowledge of their precursors and formation pathways. Here, the stable oxygen isotope composition of H2O2 for ...

AMER CHEMICAL SOC2023

Ring-Opening Reactions of Aminocyclopropanes and Aminocyclobutanes

Mingming Wang

Nitrogen-containing compounds are an important class of molecules in medicinal chemistry, chemical biology, biochemistry, material sciences or environmental sciences. Organic nitrogen occurs in many forms, ranging from small building blocks such as urea, a ...

EPFL2022

Extraction and controlled functionalization of lignin for materials applications

Stefania Bertella

Lignin is a renewable aromatic polymer that due to its abundance and unique chemical structure is a promising candidate to replace aromatic materials that are currently sourced from fossil oil. The same structure of lignin poses however drawbacks for its v ...

EPFL2022

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

Diformylxylose as a new polar aprotic solvent produced from renewable biomass

Jeremy Luterbacher, Anastasiia Komarova, Graham Reid Dick

Lignin is a promising candidate for the replacement of fossil-based materials, due to its natural abundance and aromatic structure. This same structure poses major challenges to lignin's exploitation for material development. The harsh conditions generally ...

2021

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

Production, characterization and upgrading of biomass-derived acetal-stabilized carbohydrates

Ydna Marie Questell-Santiago

Biomass is an attractive source of renewable carbon-based fuels and chemicals. Multiple research efforts are centered around integrated biorefineries, where all fractions of biomass are converted to fuels or chemical products. These efforts are focused aro ...

EPFL2019

1,3-Difunctionalization of Aminocyclopropanes via Dielectrophilic Intermediates

Jérôme Waser, Mingming Wang

We report an oxidative ring-opening strategy to transform acyl, sulfonyl or carbamate protected aminocyclopropanes into 1,3-dielectrophilic carbon intermediates bearing a halide atom (Br, I) and a N,O-acetal. Replacing the alkoxy group of the N,O-acetal ca ...

Wiley-VCH Verlag GmbH2019

Protection Group Effects During α,γ-Diol Lignin Stabilization Promote High-Selectivity Monomer Production

Jeremy Luterbacher, Masoud Talebi Amiri, Wu Lan, Christopher Marc Hunston

Protection groups were introduced during biomass pretreatment to stabilize lignin's α,γ-diol group during its extraction and prevent its condensation. Acetaldehyde and propionaldehyde stabilized the α,γ-diol without any aromatic ring alkylation, which sign ...

Wiley-VCH Verlag GmbH2018

Carbohydrate stabilization extends the kinetic limits of chemical polysaccharide depolymerization

Jeremy Luterbacher, Masoud Talebi Amiri, Ydna Marie Questell-Santiago

Polysaccharide depolymerization is an essential step for valorizing lignocellulosic biomass. In inexpensive systems such as pure water or dilute acid mixtures, carbohydrate monomer degradation rates exceed hemicellulose—and especially cellulose—depolymeriz ...

2018

Palladium-Catalyzed Vicinal Amino Alcohols Synthesis from Allyl Amines by In Situ Tether Formation and Carboetherification

Jérôme Waser, Ugo Jonathan Orcel

Vicinal amino alcohols are important structural motifs of bioactive compounds. Reported herein is an efficient method for their synthesis based on the palladium-catalyzed oxy-alkynylation, oxy-arylation, or oxy-vinylation of allylic amines. High regio- and ...

Wiley-Blackwell2015

PEG-based Multifunctional Polyethers with Highly Reactive Vinyl-Ether Side Chains for Click-Type Functionalization

Frederik Roman Wurm

Introduction of highly reactive vinyl ether moieties along a poly(ethylene-glycol) (PEG) backbone has been realized by copolymerization of the novel epoxide monomer ethoxy vinyl glycidyl ether (EVGE) with ethylene oxide (EO). A series of copolymers with va ...

American Chemical Society2011

Acetal-Functionalized RAPTA Complexes for Conjugation and Labeling

Paul Joseph Dyson, Wee Han Ang

Ruthenium-arene complexes bearing the 1,3,5-triaza-7-phosphatricyclo-[3.3.1.1]decane ligand, namely, RAPTA compounds, are widely investigated as potential antimetastatic agents for cancer therapy. Although much evidence points toward covalent binding with ...

American Chemical Society2011

New developments on silyl 2-alkenyl sulfinates and their applications to the asymmetric synthesis of polypropionate fragments

Xiaogen Huang

Sulphur dioxide reacts with 1-oxydienes generating zwitterions which are quenched by enoxysilanes to form substituted silyl alkenylsulfinates. These intermediates are desilylated with Bu4NF and the resulting sulfinates react with MeI giving the correspondi ...

EPFL2004