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Tesi etd-10212019-092509


Thesis type
Tesi di laurea magistrale LM5
Author
VITELLI, VALENTINA
URN
etd-10212019-092509
Title
Synthesis of aminoacidic phenyl sulfides as precursors for peptidic late stage halogenation
Struttura
FARMACIA
Corso di studi
CHIMICA E TECNOLOGIA FARMACEUTICHE
Supervisors
relatore Prof.ssa Di Bussolo, Valeria
relatore Prof. Adamo, Mauro
Parole chiave
  • phenyl sulfides
  • amino acids
  • halogenation
Data inizio appello
06/11/2019;
Consultabilità
Secretata d'ufficio
Data di rilascio
06/11/2089
Riassunto analitico
The synthesis of halogenated aminoacidic or peptidic compounds, due to their high biological activity, have gained a great interest in medicinal chemistry, above all for their relevance in preclinical and clinical.
A possible pathway for halogenation of these compounds involves the preventive synthesis of sulfur precursors. Indeed, S-phenyl group has shown to be a remarkable leaving group for the regiospecific attack of a halogen.
The aim of the research project presented in this thesis is the synthesis of sulfur-bearing peptides as a substrate for late stage halogenation. The main reaction is a selective addition, in alfa position with respect to the aminoacidic nitrogen, trough thia-Michael mechanism. The work is based on the attack of thiophenol or derivatives on the imminic group, formed between amine and aldehyde-derivate.
The reaction, induces the formation of a new stereocenter in the molecule, showing an evident enantiomeric or diastereomeric prevalence with up to 60% diastereomeric excess and good yields up to 70%.
The synthesis of these compounds lays the foundation for future late-stage halogenation studies.
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