In these three years, as PhD student, I was involved in different projects regarding the synthesis of new enantiopure beta-amino acids, their use for the preparation of small alpha/beta-peptide sequences and the study of their secondary structure. All hybrid alpha/beta-peptides were studied using NMR Spectroscopy (1H, 13C, HMBC, HMQC, NOESY; ROESY). Molecular modelling was also performed in collaboration with Prof. Contini, from DISFARM, Università degli Studi di Milano. In the first part of my thesis I reported on the synthesis of: - tetrahydroisoquinoline 4-carboxylic acid and its use in the preparation of alpha/beta-peptides. This new beta-amino acid, coupled with beta-Ala, can stabilize a flexible reverse turn conformation, depending on its stereochemistry; - beta-Morpholino-amino acid. This new beta-amino acid, prepared in enantiopure form, stabilizes a reverse gamma-turn conformation when inserted in alpha/beta-peptides; - beta2,3-diaryl-amino acids and preparation of alpha/beta-peptides. The secondary structure of each peptide was studied. Moreover, self-assembly of a ααβ-tripeptide composed by the beta2,3-diaryl amino acid coupled with L-Ala-L-Arg was investigated. In the second part of this thesis I focused on two other subjects beyond the beta-amino acids, that are: - the synthesis of isoxazoline containing scaffold. Also in this case, model peptides were prepared and their secondary structure were studied; it was found that our scaffold induce a turn able to stabilize a beta-hairpin. - the synthesis and study on Double Functionalized Collagen Model Peptides. This part of my thesis was performed during my internship at ETH (Eidgenössische Technische Hochschule, Zürich, Switzerland) in Wennemers Group.
CONSTRAINED BETA-AMINO ACIDS AS MOLECULAR TOOLS FOR THE PREPARATION OF FOLDAMERS / R. Bucci ; tutor: M. L. Gelmi ; coordinator: G. Aldini. - Milano : Università degli studi di Milano. DIPARTIMENTO DI SCIENZE FARMACEUTICHE, 2018 Jan 19. ((30. ciclo, Anno Accademico 2017.
|Titolo:||CONSTRAINED BETA-AMINO ACIDS AS MOLECULAR TOOLS FOR THE PREPARATION OF FOLDAMERS|
|Supervisori e coordinatori interni:||ALDINI, GIANCARLO|
|Data di pubblicazione:||19-gen-2018|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Citazione:||CONSTRAINED BETA-AMINO ACIDS AS MOLECULAR TOOLS FOR THE PREPARATION OF FOLDAMERS / R. Bucci ; tutor: M. L. Gelmi ; coordinator: G. Aldini. - Milano : Università degli studi di Milano. DIPARTIMENTO DI SCIENZE FARMACEUTICHE, 2018 Jan 19. ((30. ciclo, Anno Accademico 2017.|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.13130/r-bucci_phd2018-01-19|
|Appare nelle tipologie:||Tesi di dottorato|