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Université de Fribourg

Photochemical C–H activation: generation of indole and carbazole libraries, and first total synthesis of clausenawalline D

Alimi, Isak ; Remy, Richard ; Bochet, Christian G.

In: European Journal of Organic Chemistry, 2017, vol. 2017, no. 22, p. 3197–3210

The photolysis of N-aryltriazoles and N-arylbenzotriazoles leads to indoles and carbazoles, respectively. Because libraries of triazoles can be accessed rapidly, for example by the copper-catalyzed [3+2] cycloaddition reaction between alkynes and azides, this reaction allows the preparation of indoles in a single operation, by the simultaneous photolysis of the precursor library. As an example of...

Université de Fribourg

Bis-retinoid A2E induces an increase of basic fibroblast growth factor via inhibition of extracellular signal-regulated kinases 1/2 pathway in retinal pigment epithelium cells and facilitates phagocytosis

Balmer, Delphine ; Bapst-Wicht, Linda ; Pyakurel, Aswin ; Emery, Martine ; Nanchen, Natacha ; Bochet, Christian G. ; Roduit, Raphael

In: Frontiers in Aging Neuroscience, 2017, vol. 9, p. -

Age-related macular degeneration (ARMD) is the leading cause of vision loss in developed countries. Hallmarks of the disease are well known; indeed, this pathology is characterized by lipofuscin accumulation, is principally composed of lipid-containing residues of lysosomal digestion. The N-retinyl-N-retinylidene ethanolamine (A2E) retinoid which is thought to be a cytotoxic component for RPE...

Université de Fribourg

Activity-dependent structural plasticity of perisynaptic astrocytic domains promotes excitatory synapse stability

Bernardinelli, Yann ; Randall, Jerome ; Janett, Elia ; Nikonenko, Irina ; König, Stéphane ; Jones, Emma Victoria ; Flores, Carmen E. ; Murai, Keith K. ; Bochet, Christian G. ; Holtmaat, Anthony ; Muller, Dominique

In: Current Biology, 2014, vol. 24, no. 15, p. 1679–1688

Excitatory synapses in the CNS are highly dynamic structures that can show activity- dependent remodeling and stabilization in response to learning and memory. Synapses are enveloped with intricate processes of astrocytes known as perisynaptic astrocytic processes (PAPs). PAPs are motile structures displaying rapid actin-dependent movements and are characterized by Ca²⁺ elevations in...

Université de Fribourg

Synthesis of different glutathione–sulfur mustard adducts of verified and potential biomarkers

Bielmann, Andreas ; Sambiagio, Nicolas ; Wehr, Nathalie ; Gerber-Lemaire, Sandrine ; Bochet, Christian G. ; Curty, Christophe

In: RSC Advances, 2018, vol. 8, no. 42, p. 23881–23890

Sulfur Mustard (SM) is a blistering agent used as a chemical weapon. Glutathione (GSH) is involved in the β-lyase degradation pathway of SM and recently, bioadducts between SM and GSH were observed in vitro. While these bioadducts have never been isolated from in vivo tests or real poisoning with SM, they could be of interest as potential future biomarkers for the retrospective validation of...

Université de Fribourg

Solid‐phase synthesis of the aged‐nonapeptide‐nerve‐agent adduct of butyrylcholinesterase as reference materials for analytical verification

Bielmann, Andreas ; Curty, Christophe ; Bochet, Christian G.

In: Helvetica Chimica Acta, 2017, vol. 100, no. 11, p. -

Two pathways were developed and investigated for the synthesis of the ‘aged’- nonapeptide nerve-agent bioadduct of human butyrylcholinesterase (BuChE). Considering the fast ageing of nerve-agent adducts of BuChE in patients and biomedical samples this target molecule is of paramount relevance for quantitative analysis with respect to the Chemical Weapons Convention. Two approaches using a ...

Université de Fribourg

Photochemistry of allenyl salicylaldehydes

Birbaum, Frédéric ; Neels, Antonia ; Bochet, Christian G.

In: Organic Letters, 2008, vol. 10, no. 15, p. 3175–3178

The intramolecular photocycloaddition of aryl aldehydes containing allene side chains is a versatile reaction as it provides a rapid and efficient access to original complex structures such as 1,3,4-tetrahydro-1,4-epoxy-5-alkylidene-2-benzoxepines 2 and substituted 2-oxa-tricyclo[5.2.2.0]1,5undeca-4,8,10-triene-9-carbaldehydes 3. Novel polycyclic structures are...

Université de Fribourg

Isotope effects in photochemistry: application to chromatic orthogonality

Blanc, Aurélien ; Bochet, Christian G.

In: Organic Letters, 2007, vol. 9, no. 14, p. 2649-2651

The main challenge in developing new wavelength-specific photolabile protecting groups is the rigorous control of the photolysis rate. This rate is controlled by two factors: the chromophore absorbance and the reaction quantum yield. Fine-tuning the properties by changing substituents or structural features is difficult, because both factors are independently affected. By the use of the kinetic...

Université de Fribourg

Towards a photochemical synthesis of peptides

Bochet, Christian G.

In: CHIMIA International Journal for Chemistry, 2013, vol. 67, no. 12, p. 896–898

The laboratory preparation of peptides, once a challenge, is now a standard operation that can be automatised. However, the need for particular protecting groups requiring relatively harsh conditions for their removal (strong acids or bases) and reactive coupling agents can be problematic in specific cases (e.g. in a cell or in a microfluidic device). In this account, we describe our efforts...

Université de Fribourg

Hard work and light experience: early steps in photochemistry

Bochet, Christian G.

In: Chimia, 2009, vol. 63, no. 12, p. 872-873

The author describes his early steps as an independent researcher at the University of Geneva. His interest in synthetic organic photochemistry came from his past non-experience at the Universities of Geneva and Stanford, where he worked mainly on natural product synthesis and transition-metal catalysis.