Skip to Main content Skip to Navigation
Theses

Dynasweet - Les glycodyn[n]arènes comme ligands multivalents de lectines : une étude par chimie combinatoire dynamique

Yoann Pascal 1
1 LCO2 - Laboratoire de Chimie Organique 2 Glycochimie
MSMB - Méthodologie de synthèse et molécules bioactives
Abstract : Several glycoclusters based on calixarenes, pillararenes or fullerenes have been synthesized in our laboratory. They exhibited strong affinities for several lectins through their multivalence and the “glycoside cluster effect”. The prupose of this study was to add a dynamic part to these molecules. We therefore applied the concept of dynamic combinatorial chemistry in which building blocks are able to self-assemble through reversible bonds to generate a library of oligomers. Dithiophenols bearing carbohydrate epitopes can self-assemble through the formation and exchange of disulfide bonds. Their properties in dynamic combinatorial chemistry were studied and the species distribution at the thermodynamic equilibrium revealed the selective formation of cyclotrimers and cyclotetramers named dyn[3]- and dyn[4]arenes. The equilibration in the presence of ConA, used as a model lectin, have led to the amplification of homodyn[3]- and homodyn[4]arenes. These glycodyn[n3,4]arenes have been isolated and their affinities toward ConA measured by ITC in the nanomolar range. Extension of this methodology toward the lectins LecA and LecB of Pseudomonas aeruginosa is in progress
Document type :
Theses
Complete list of metadatas

Cited literature [253 references]  Display  Hide  Download

https://tel.archives-ouvertes.fr/tel-02076550
Contributor : Abes Star :  Contact
Submitted on : Friday, March 22, 2019 - 11:04:09 AM
Last modification on : Wednesday, November 20, 2019 - 3:24:00 AM
Long-term archiving on: : Sunday, June 23, 2019 - 1:50:47 PM

File

TH2018PASCALYOANN.pdf
Version validated by the jury (STAR)

Identifiers

  • HAL Id : tel-02076550, version 1

Collections

Citation

Yoann Pascal. Dynasweet - Les glycodyn[n]arènes comme ligands multivalents de lectines : une étude par chimie combinatoire dynamique. Chimie organique. Université de Lyon, 2018. Français. ⟨NNT : 2018LYSE1288⟩. ⟨tel-02076550⟩

Share

Metrics

Record views

175

Files downloads

218