Self-mineralization and assembly of a bis-silylated Phe–Phe pseudodipeptide to a structured bioorganic–inorganic material

International audienceSelf-mineralization of trialkoxysilyl hybrid peptide yield in a single step a nanostructured hybrid material. A bis-silylated pseudodipeptide inspired from the Phe-Phe dipeptide was used to program the assembly by sol-gel polymerization in heterogeneous conditions, in water at pH 1.5 without any structure-directing agent. A mechanism deciphering the hybrid material assembly was proposed thanks to 1H NMR spectroscopy. First, water-insoluble hybrid building blocks were hydrolysed into their soluble silanol counterparts. Then, these transitional species, thanks to hydrogen bonding and π-π stacking, self-assembled in solution. Last, the proximity of silanol moieties favoured their polycondensation into growing siloxane oligomers, which spontaneously precipitated to produce an ordered hybrid material

Synthese et activites biologiques de divers analogues lineaires et cycliques de la cholecystokinine

SIGLEAvailable from INIST (FR), Document Supply Service, under shelf-number : T 81808 / INIST-CNRS - Institut de l'Information Scientifique et TechniqueFRFranc

Synthèse et études structurales d'oligomères de mimes contraints de dipeptide (recherche de nouveaux foldamères)

MONTPELLIER-BU Sciences (341722106) / SudocSudocFranceF

A simple and versatile method to synthesize N-acylbenzotriazoles

International audienceAn efficient method for the synthesis of N-acyl-benzotriazoles from a wide variety of protected amino acids, as well as from compounds frequently used in drug discovery such as biotin and N-Fmoc polyethylene glycol, has been developed. The reaction of carboxylic acid derivatives with benzotriazole in the presence of T3P_ yielded the corresponding N-acyl-benzotriazoles, which were obtained in high purity following a simple work-up procedure, in most cases via precipitation of the desired product in water

Structures hélicoïdales d'hligomères dirigées par un béta-Amino acide bicyclique

Ce travail de thèse est consacré à la synthèse et la caractérisation structurale par spectroscopies RMN, IR, CD et RX de nouveaux oligomères non naturels qui s'inscrivent dans la famille des foldamères. Ils sont construits en particulier à partir d'un b-aminoacide bicyclique chiral original: l'acide (S)- ou (R)-aminobicyclo[2.2.2]octane-2-carboxylique ((S)- et (R) ABOC) que nous avons développé. Ce motif est issu d'une synthèse stéréocontrollée, dont l'étape clef est une réaction de Diels-Alder asymétrique. Après avoir montré que ce motif est un mime de coude peptidique il a été utilisé pour la synthèse de plusieurs séries d'oligomères. Deux grandes familles ont été développées: des oligourées et des oligoamides. A l'intérieur de ces familles, des homo- et des hétéro-oligomères ont été synthétisés et leur préférence conformationnelle a été définie. Les analyses RMN et les études cristallographiques ont permis de montrer qu'en fonction de leur séquence ils sont capables d'adopter plusieurs types d'hélices. Les homo-oligourées d'ABOC et des hétéro-oligourées alternant l'ABOC et des b3-aminoacides ont conduit à des hélices-12/14. Les oligoamides construits par des alternances d'ABOC et de b3-aminoacides dans un rapport 1/1 et des alternances d'ABOC et d'a-aminoacides dans un rapport 1/1 ou 1/2 ont conduit respectivement à des hélices 10/12, 16/18 et 12/14.This thesis is devoted to the synthesis and FT-IR, CD, NMR and X-ray structural characterization of new unnatural oligomers belonging to the family of foldamers. In particular they are constructed from an original chiral bicyclic b-amino acid: (S)- and (R)-aminobicyclo[2.2.2]octane-2-carboxylic acid ((S) - and (R) ABOC ) that we have developed. This motive was obtained via a stereocontrolled synthesis using an asymmetric Diels-Alder reaction as key step. Firstly, this motive was shown to induce turn in peptide sequence and then it was used for the synthesis of several series of oligomers. Two main families were developed: oligoureas and oligoamides. Within these families, homo-and hetero-oligomers were synthesized and their conformational preferences were defined. NMR analysis and crystallographic studies have shown that depending on their sequence they are able to adopt several types of helices. ABOC homo-oligoureas and hetero-oligoureas containing both ABOC residue and b3-amino acid favor a 12/14-helix. Oligoamides with 1/1 alternation of ABOC and b3-amino acids, and heterogeneous backbones with 1/1 and 1/2 ABOC/a-amino acid residue patterns adopt 10/12-, 16/18- and 12/14-helix, respectively.MONTPELLIER-BU Sciences (341722106) / SudocSudocFranceF

Unexpected Reactivity of N -Acyl-Benzotriazoles with Aromatic Amines in Acidic Medium (ABAA Reaction)

International audienc

PROteolysis TArgetting Chimeras (PROTACs) strategy applied to kinases: recent advances

International audienc

Methods and Protocols of Modern solid phase peptide synthesis

International audienc

Methods and Protocols of Modern solid phase peptide synthesis

International audienc