A5089935543- Chemical Synthesis and Analysis
- Organoboron and organosilicon chemistry
- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Crystallography and molecular interactions
- Radiopharmaceutical Chemistry and Applications
- Neuropeptides and Animal Physiology
- Asymmetric Hydrogenation and Catalysis
- Asymmetric Synthesis and Catalysis
- Neuroendocrine Tumor Research Advances
- Organophosphorus compounds synthesis
- Peptidase Inhibition and Analysis
- Catalytic C–H Functionalization Methods
- Catalytic Cross-Coupling Reactions
- Lung Cancer Research Studies
- Receptor Mechanisms and Signaling
- Antimicrobial Peptides and Activities
- Fermentation and Sensory Analysis
- Food Quality and Safety Studies
- Click Chemistry and Applications
- Chemical synthesis and alkaloids
- Mass Spectrometry Techniques and Applications
- Ferrocene Chemistry and Applications
- Polyamine Metabolism and Applications
- Synthesis and Catalytic Reactions
Institut des Biomolécules Max Mousseron
2016-2025
Université de Montpellier
2015-2025
Centre National de la Recherche Scientifique
2015-2025
École Nationale Supérieure de Chimie de Montpellier
2016-2025
Unité de recherche sur les maladies cardiovasculaires et métaboliques
2020
Bipar
2020
Université de Bourgogne
2010-2015
Institut de Chimie
2010-2015
Institut de Chimie Moléculaire de l'Université de Bourgogne
2010-2015
Osaka University
2011-2014
The reaction of aryl cyanides with diboron in the presence a rhodium/Xantphos catalyst and DABCO affords arylboronic esters via carbon-cyano bond cleavage. This unprecedented mode reactivity for borylrhodium species allows regioselective introduction boryl group late stage synthesis.
The P-chirogenic organocatalysts were found to promote the enantioselective aza-Morita-Baylis-Hillman reaction of ketimines derived from acyclic α-keto esters. In organocatalyzed aza-MBH reactions, α,α-disubstituted α-amino acid derivatives obtained in high yields with enantioselectivities (up 97% ee).
An efficient and general method for the preparation of achiral chiral phosphonium salts is reported. This synthesis based on quaternization phosphines their derivatives with arynes generated in situ from 2-(trimethylsilyl)aryl triflates. methodology successfully applied to new valuable P-stereogenic
Tumor heterogeneity remains one of the main obstacles for cancer diagnosis and treatment. The simultaneous targeting several biomarkers is an appealing approach improved diagnostic procedures. Neurotensin receptor 1 (NTS1) Gastrin‐Releasing Peptide Receptor (GRPR) are both G‐protein coupled receptors with complementary profile expression in types. This work proposes design, synthesis vitro radiopharmaceutical characterization three heterodimers, based on GRP/NT modified peptides,...
Peptide-based radiopharmaceuticals targeting neurotensin-receptor-1 (NTS1) are mainly stabilized using chemical modifications at the NT[8–13] sequence, thus increasing stability and uptake of corresponding radionuclide-macrocycle-linker-bioconjugate. We postulate that introduction linker N-term part induces additional cleavage sites can be further to achieve a prolonged uptake. Double (JMV 7259 JMV 7222) triple-stabilized neurotensin analogues 7258 7490) were synthesized, radiolabeled,...
The stereoselective synthesis of P-chirogenic phosphines bearing an o-hydroxyalkyl chelating arm is described. based either on the hydroxyalkylation o-bromophenylphosphines (borane) or their carbonatation and then reduction. with benzaldehyde pivalaldehyde affords a mixture epimers which are isolated by chromatography characterized X-ray structures. Preliminary assays free o-(hydroxyalkyl)phenyl phosphines, as new functional Lewis bases in catalyzed asymmetric aza-MBH reaction, lead to...
The synthesis of phospholyl(borane) amino acids was stereoselectively achieved by reaction phospholide anion with iodo α-amino ester derived from l-aspartic acid or l-serine, followed in situ complexation borane. Phospholyl(borane) are easy to store and can be subjected direct transformation into the corresponding free phospholyl, gold complex, oxide sulfur derivatives as well phospholinium salts, thus offering a variety side chains. After selective deprotection carboxylic function amine, C-...
An efficient synthesis of boronated phosphines with an o-phenylene-bridge prepared from sec-phosphine boranes and using benzyne chemistry is reported. Successive reactions n-BuLi 1,2-dibromobenzene, then boron reagents, afford the o-boronatophenylphosphine derivatives in 71% yields. The use P-chirogenic leads to free retention configuration at P-center after decomplexation. reaction KHF2 affords corresponding trifluoroborated phosphine ee >98%.
Strategies for the preparation of phosphorus-containing amino acids and their utility in organic chemistry, physico-chemistry, agrochemistry, pharmacology fields are reported.
The stereoselective synthesis of a new amino acid phosphonium salt was described by quaternization melting triphenylphosphine with the γ-iodo NHBoc-amino ester, derived from L-aspartic acid. deprotection carboxylic function to afford free group achieved palladium-catalyzed desallylation reaction. This used in Wittig reaction aromatic or aliphatic aldehydes and trifluoroacetophenone, under solid-liquid phase-transfer conditions chlorobenzene presence K(3)PO(4) as weak base, corresponding...
A new rhodium-catalyzed method for preparing arylboronates from aryl cyanides through the cleavage of carbon–cyano bonds is described. This unprecedented transformation nitriles allows use a cyano group as boryl equivalent and regioselective introduction at late stage synthesis.
Linker and chelating agents strongly influence the binding affinity of NTS 1 -PSMA heterobivalent probe towards . Comparable affinities between mono- ligands PSMA were observed.
Abstract A proof of concept for the asymmetric organocatalytic aza‐Michael addition reaction nitrogen nucleophiles with simple and readily available alkyl enoates as acceptor molecules in presence a chiral phase‐transfer catalyst has been demonstrated. The desired enantiomerically enriched β‐amino acid derivatives were obtained up to 86% yield enantioselectivities 37% ee. © 2012 Wiley Periodicals, Inc. Heteroatom Chem 23:202–209, 2012; View this article online at wileyonlinelibrary.com . DOI...
Therapeutic hypothermia represents a brain-protective strategy for multiple emergency situations, such as stroke or traumatic injury. Neurotensin (NT), which exerts its effects through activation of two G protein-coupled receptors, namely NTS1 and NTS2 induces strong long-lasting decrease in core body temperature after central administration. Growing evidence demonstrates that is the receptor subtype mediating hypothermic action NT. As such, potent agonists designed on basis minimal...
Several independent studies have demonstrated the overexpression of NTS1 in various malignancies, which make this receptor interest for imaging and therapy. To date, radiolabeled neurotensin analogues suffer from low plasmatic stability thus insufficient availability high uptake tumors. We report development 68Ga-radiolabeled with improved radiopharmaceutical properties through introduction silicon-containing amino acid trimethylsilylalanine (TMSAla). Among series novel analogues,...
Abstract A series of new unnatural amino acids bearing a β‐arylthiazole side chain was synthesized by exploiting diastereoselective alkylation starting from glycine tert ‐butyl ester Schiff base with hydroxypinanone as the chiral inducer. This strategy afforded alanines in good chemical yields and 98 % ee . Due to their aromatic properties, these newly generated were used prepare neurotensin (NT)[8–13] analogues serving replacements for native Tyr11 residue. Incorporation ( L...
Synthesis of fluorescent P-hydroxybinaphtylphosphole-oxide or -sulfide was achieved by trapping a binaphtyl dianion with methyl dichlorophosphite P-(N,N-diethylamino)dichlorophosphine, followed oxidation sulfuration the P-center. After saponification acid hydrolysis, P-hydroxyphospholes were coupled to peptides using coupling agent BOP, under conditions required for synthesis in solution on solid support. This new method illustrated labeling JMV2959, potent antagonist Growth Hormone...
Abstract Modular hemisyntheses of boronato‐ and trifluoroborato‐substituted amino acid peptide derivatives by using Wittig C–H iridium‐catalyzed borylation as key reactions, are described. Amino ester precursors bearing an aromatic moiety on a lateral chain were prepared reaction new L ‐NHBoc‐amino reagent with the corresponding aldehydes. After esterification hydrogenation, esters was achieved yields up to 82 % catalysed bis(pinacolato) diborane (B 2 Pin ) in presence iridium complex....
Neurotensin receptor 2 (NTS2) is a well-known mediator of central opioid-independent analgesia. Seminal studies have highlighted NTS2 overexpression in variety tumors including prostate cancer, pancreas adenocarcinoma, and breast cancer. Herein, we describe the first radiometalated neurotensin analogue targeting NTS2. JMV 7488 (DOTA-(βAla)2-Lys-Lys-Pro-(D)Trp-Ile-TMSAla-OH) was prepared using solid-phase peptide synthesis, then purified, radiolabeled with 68Ga 111In, investigated vitro on...
The synthesis of silole amino acids was achieved through hydrosilylation alkene or alkyne‐containing with 1‐methyl‐2,3,4,5‐tetraphenyl‐1H‐silole, using Karstedt's catalyst yield up to 95 % and without epimerization. After selective deprotection carboxylic acid amine functions respectively, C‐ N‐peptide coupling an alanine moiety proved their possible incorporation into peptides. A model tripeptide synthesized by solid phase the N‐Fmoc protected version. can be also grafted on a precursor...