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Archivio digitale delle tesi discusse presso l’Università di Pisa

Tesi etd-09092021-121658


Tipo di tesi
Tesi di laurea magistrale LM5
Autore
BARBINI, GABRIELE
URN
etd-09092021-121658
Titolo
New Stereoselective Synthesis of Glyco-based scaffolds: Pyran-dioxane Polycycles and Chiral Lanthanide Complexes
Dipartimento
FARMACIA
Corso di studi
CHIMICA E TECNOLOGIA FARMACEUTICHE
Relatori
relatore Prof.ssa Di Bussolo, Valeria
relatore Dott. Di Pietro, Sebastiano
relatore Dott.ssa Iacopini, Dalila
Parole chiave
  • Lanthanide Complexes
  • Polycycle
  • Pyran-Dioxane
  • Stereoselectivity
  • Vinyl-epoxide
Data inizio appello
04/10/2021
Consultabilità
Completa
Riassunto
Pyran-dioxane-based polycycles are found in several natural compounds, most of them characterized by a biological activity with pharmaceutical applications. The specific geometry of the polycyclic scaffold is often intimately connected with their biological activity since from that stems their capability of recognizing and bound specifical targets. Among these classes of molecules can be found in well-known groups of medicines such as Anthracyclines, Angucyclines, some cardiac glycosides, and Spectinomycin. Due to the tight connection between geometry and biological activity, the main challenge for the synthesis of these cyclic scaffolds is represented by the stereocontrol over the key chemical processes that led to the formation of these compounds from the chosen building block, the β-hydroxyl-mesylate.
The other main topic of my thesis concerns new glycol chiral luminescent Ln(III) complexes. Ln(III) complexes find various applications in analytical chemistry and biomedicine due to their capability of being circular polarized luminescence (CPL) emitters. As CPL emitters, these complexes can be used as probes capable of changing their emission spectra when bound to specific targets. Lanthanides(III) ions have weak absorption and emission; this disadvantage can be overcome using chromophores coordinated with the metal ions, capable of absorbing the energy from the excitation source and transfer it to the ion enhancing its emission. Different types of chiral Ln(III) complexes have been synthesized, however carbohydrates complexes have not yet been more exploited; since that, the main target of this thesis work was represented by the synthesis of new chiral carbohydrate-based lanthanide probes.
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