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Design, synthesis and structural evaluation of peptidomimetics with a defined secondary structure

URN to cite this document: urn:nbn:de:bvb:355-opus-11050

Delatouche, Régis (2009) Design, synthesis and structural evaluation of peptidomimetics with a defined secondary structure. PhD, Universität Regensburg

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Abstract (English)

The synthesis of new delta-amino acids based on a gamma-butyrolactone ring was performed and they were inserted into various peptidomimetics for conformational studies. Some non-substituted and substituted butyrolactone building blocks were prepared by various methods. Then, homopeptides as well as mixed peptides were prepared and their secondary structures analysed by various techniques including 2d-NMR, CD spectroscopy and IR in solution.
In the second part of this project, some building blocks based on a diketopiperazine scaffold were prepared and inserted into homopolymers and cyclic peptidomimetics for secondary structure evaluation. In addition to these peptides, some potential organocatalysts containing the diketopiperazine scaffold were also prepared.

Translation of the abstract (German)

Durchgeführt wurde die Synthese von neuen, auf einen gamma-Butyrolaktonring basierenden, delta-Aminosäuren und deren Einbau in verschiedene Peptidomimetika für Konformationstudien. Einige unsubstituierte sowie funktionalisierte gamma-Butyrolakton Einheiten wurden dargestellt. Anschließend wurden Homo-Peptide und gemischte Peptide dargestellt und deren Sekundärstruktur durch verschiedene Analysetechniken (2D-NMR, CD-Spektroskopie und IR) bestimmt.
Im zweiten Teil der Arbeit wurden einige, auf Diketopiperazin Grundgerüst basierende, Bausteine dargestellt und in Homopolymere und zyklische Peptidomimetika eingebaut und deren Sekundärstruktur untersucht. Zudem wurden ein paar potentielle Organokatalysatoren mit Diketopiperazin-Grundgerüst dargestellt.

Item Type:

Thesis of the University of Regensburg (PhD)

Referee:

Oliver (Prof. Dr.) Reiser

Date of exam:

03 December 2008

Institutions:

Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser

Classification:

Notation	Type
92E99	MSC

Keywords:

Peptide , Peptidsynthese , Peptid-Bindung , Synthetische Peptide , Cyclopeptide , Piperazindion <2,5-> , Peptidomimetikum , Molekulardesign , , delta amino acid , diketopiperazine , peptidomimetics , unnatural amino acid , secondary structure , gamma butyrolactone

Subjects:

500 Science > 540 Chemistry & allied sciences

Status:

Published

Refereed:

Yes, this version has been refereed

Created at the University of Regensburg:

Yes

Owner:

Universitätsbibliothek Regensburg

Deposited On:

14 Jan 2010 16:25