Synthesis of unusual alpha-amino acids and study of the effect of their incorporation into antimicrobial peptides. Total synthesis of biactive marine natural products and analogues thereof

The principle theme of this thesis was the synthesis of bioactive compounds. To this end, this work was focus on two main projects. The first one, which was carried out in the Department of Chemistry of the University of Girona under the supervision of Dr Montserrat Heras, concerned the synthesis of...

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Detalles Bibliográficos
Autor: El Marrouni El Ghazaoui, Abdellatif
Tipo de recurso: tesis doctoral
Estado:Versión publicada
Fecha de publicación:2012
País:España
Institución:CBUC, CESCA
Repositorio:TDR. Tesis Doctorales en Red
OAI Identifier:oai:www.tdx.cat:10803/80815
Acceso en línea:http://hdl.handle.net/10803/80815
Access Level:acceso abierto
Palabra clave:Pèptids antimicrobials
Péptidos antimicrobianos
Antimicrobial peptides
Compostos bioactius
Compuestos bioactivos
Bioactive compounds
Marine natural products
Unnatural amino acids
Aminoàcids no naturals
Aminoácidos no naturales
Productes naturals marins
Productos naturales marinos
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Descripción
Sumario:The principle theme of this thesis was the synthesis of bioactive compounds. To this end, this work was focus on two main projects. The first one, which was carried out in the Department of Chemistry of the University of Girona under the supervision of Dr Montserrat Heras, concerned the synthesis of new unnatural amino acids bearing a pyrimidine ring within their side chain for incorporation into the antimicrobial peptide BP100 following a rational design in order to improve its biological profile. On the other hand, the second chapter of this thesis was developed in collaboration with the Laboratoire de Chimie Organique (ESPCI-ParisTech, Paris, France) under the guidance of Pr Janine Cossy and Dr Arseniyadis. This chapter was centered on the total synthesis of three marine natural products with complex structures and interesting biological activities: acremolide B, (–) bitungolide F and lyngbouilloside.