A5071718348- Chemical Synthesis and Analysis
- Carbohydrate Chemistry and Synthesis
- Mass Spectrometry Techniques and Applications
- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Enzyme Production and Characterization
- Amino Acid Enzymes and Metabolism
- Peptidase Inhibition and Analysis
- Radiopharmaceutical Chemistry and Applications
- Receptor Mechanisms and Signaling
- Analytical Chemistry and Chromatography
- Legume Nitrogen Fixing Symbiosis
- Bioactive Compounds and Antitumor Agents
- Polydiacetylene-based materials and applications
- Fluorine in Organic Chemistry
- Neuropeptides and Animal Physiology
- Cell death mechanisms and regulation
- Supramolecular Self-Assembly in Materials
- Click Chemistry and Applications
- Pharmacological Effects and Assays
- Plant biochemistry and biosynthesis
- Catalytic C–H Functionalization Methods
- Regulation of Appetite and Obesity
- Metal complexes synthesis and properties
- Advanced Physical and Chemical Molecular Interactions
Institut des Sciences Chimiques de Rennes
2008-2024
École Nationale Supérieure de Chimie de Rennes
2017-2022
Centre National de la Recherche Scientifique
2003-2021
Université de Rennes
2009-2021
Université Rennes 2
2019-2020
Université Paris Cité
2003-2004
Sorbonne Université
2003-2004
Laboratoire de Chimie Moléculaire
2004
Laboratoire de Chimie Organique
2004
26RFa, a novel RFamide neuropeptide, is the endogenous ligand of former orphan receptor GPR103. Intracerebroventricular injection 26RFa and its C-terminal heptapeptide, 26RFa((20-26)), stimulates food intake in rodents. To develop potent, stable ligands GPR103 with low molecular weight, we have designed series aza-β(3)-containing 26RFa((20-26)) analogues for their propensity to establish intramolecular hydrogen bonds, evaluated ability increase [Ca(2+)](i) GPR103-transfected cells. We...
Molecular mechanics calculations on conformers of Ac‐HGly‐NHMe, Ac‐β 2 ‐HAla‐NHMe and 3 indicate that low‐energy conformations the β‐amino acids backbone, corresponding to gauche rotamers around Cα–Cβ bond, may overlap canonical backbone observed for α‐amino acids. Therefore, Substance P (SP) was used as a model peptide analyse structural biological consequences substitution Phe7 Phe8 by (R)‐β ‐HPhe Gly9 HGly ‐HAla or (S)‐β ‐HAla. [(R)‐β ‐HAla9]SP has pharmacological potency similar SP while...
Abstract The reaction of several alkylglucosides with phenyl boronic acid permitted easy access to a series alkylglucoside boronate derivatives. This type compound has structures similar those known benzylidene glucoside organogelators except for the presence function in place acetal one. Low very low concentrations these amphiphilic molecules produced gelation organic solvents. rheological properties corresponding soft materials characterized them as elastic solids. They were further by SEM...
Abstract The yield of metallation methionine‐enkephalin and leucine‐enkephalin isomers by copper(II) chloride was investigated electrospray ionization ion trap mass spectrometry (ESI‐ITMS) in negative mode. Binary ([(M3H)+Cu II ] − ) ternary ([(M2H)+Cu Cl] complexes were observed. Soft hard desolvation conditions (by changing the declustering voltage) applied to study their influence on observed deprotonated metallated species. Structures binary with defined charge locations are proposed,...
Embelin is a natural product, inhibitor of XIAP (X-chromosome-linked Inhibitor APoptosis) with strong proapoptotic properties on cancer cells. In order to clarify the role two OH groups benzoquinone core, we have prepared by hemisynthesis close analogs embelin, where these been replaced in systematic manner OMe and OAc groups. Proapoptotic activities six embelin derivatives studied as single agent, or combination TRAIL, their abilities interact evaluated Surface Plasmon Biacore. Our results...
Photoreactive analogues of substance P (biotin sulfone-spacer (amino pentanoic or Gly(3))-Arg-Pro-Lys-Pro-(pBzl)Phe-Gln-Phe-Phe-Gly-Leu-Met(O(2))NH(2)) with without isotope (deuterium) labeling have been synthesized. Deuteriums were present on (d)-biotin epibiotin sulfone (D(3)), the Gly(3) spacer linker (D(6)), Gly in position 9 SP (D(2)). Therefore, peptide could be either unlabeled tri-, penta-, hexadeuterated. Results obtained use these show that and are not recognized same affinity by...
Starting from easily accessible gem-difluoropropargylic derivatives, a DBU-mediated isomerisation affords enones in fair yields with gem-difluoroalkyl chain. These derivatives were used to prepare pyrazolines and pyrrolines the desired side chain by cyclocondensations good excellent stereoselectivity. A one-pot process was also successfully developed for these sequential reactions. By carrying out various types of Pd-catalyzed coupling reactions compounds p-bromophenyl substituent route...
Context. Most of the molecules identified in interstellar medium (ISM) are organic compounds and more than 50 have one isomer or more. Statistically, most stable a given chemical formula is abundant. This occurrence verified up to ~90% detected species leading so-called minimum energy principle (MEP). Aims. Our main objective increase list 14 bis-nitrogen already detected. We focus on ten C x H y N z families with = (1, 2, 3), (0, 4, 6, 8), 2. To this end, we look for reliable economic way...
Abstract Peptide metallation with Cu 2+ was explored in the negative ESI mode using an ion trap mass spectrometer. Under these conditions, [(M − 3H) + II ] species formed were investigated under low‐energy collision‐induced dissociation conditions. MS 2 experiments indicate a very different behavior of metallated complexes compared [M H] species. induces easy loss CO and specific side‐chain cleavages (by radical losses) at C‐terminal residue, as observed previously by prompt ‘in source’...
Koenigs-Knorr glycosylation of acceptors with more than one free hydroxyl group by 2,3,5,6-tetrabenzoyl galactofuranosyl bromide was performed using diphenylborinic acid 2-aminoethyl ester (DPBA) as inducer regioselectivity. High regioselectivity for the on equatorial acceptor obtained thanks to transient formation a borinate adduct corresponding 1,2-cis diol. Nevertheless orthoester byproducts hampered efficiency method. Interestingly electron-withdrawing groups O-6 or C-1 displaced...
New chroman-4-ones with <i>gem</i>-difluoroalkyl side chains in position 2 are easily accessible five steps from salicylaldehyde-type derivatives. The crucial intermediates propargylic alcohols bearing a CF<sub>2</sub>R substituent on the triple bond and key step is their based-mediated isomerization into corresponding enones. After MOM deprotection, an intramolecular oxa-Michael addition affords target molecules good overall yields. Such chromanones appear as useful for preparation of...
During the investigation of water-sensitivity (arylboronate alkylglucoside)-based organogels, we evaluated a series twelve potential organogelators. They were synthesised in single step from corresponding arylboronic acids and alkylglucosides. Eight them showed organogelation abilities three solvents (toluene, cyclohexane, ethyl myristate). Conformational minimisations organogelators permitted clear relationship between arylboronate orientation gelation effectiveness to be established. These...
Galactofuranoconjugates are rare compounds with interesting biological properties. Their syntheses by traditional approaches however tedious. Glycosidases nowadays often used to simplify such but the use of galactofuranosidase has not been described yet for synthesis galactofuranoconjugates. Interestingly CtAraf51, an α-l-arabinofuranosidase from Ruminiclostridium thermocellum, is able aryl- or alkyl-β-d-galactofuranosides as substrate very low efficiency. To allow its a tool, we decided...
Standard glycosylation of unprotected 6-fluorogalactofuranoside turned to three competitive reactions and afforded difuranosides able impact growth <italic>Leishmania tarentolae</italic>.
This paper describes the synthesis and biological evaluation of new inhibitors anti-apoptotic proteins towards novel anti-cancer agents.
Proline racemases (PRAC), catalyzing the l-proline and d-proline interconversion, are essential factors in eukaryotic pathogens such as Trypanosoma cruzi, vivax, Clostridioides difficile. If discovery of irreversible inhibitors T. cruzi PRAC (TcPRAC) led to innovative therapy Chagas disease, no CdPRAC have been discovered date. However, C. difficile, due an increased incidence recent years, is considered a major cause health threat. In this work, we taken into account similarity between...
The synthesis of disaccharides, particularly those containing hexofuranoside rings, requires a large number steps by classical chemical means. use glycosidases can be an alternative to limit the steps, as they catalyze formation controlled glycosidic bonds starting from simple and easy access building blocks; main drawbacks are yields, due balance between hydrolysis transglycosylation these enzymes, enzyme-dependent regioselectivity. To improve yield...