Please use this identifier to cite or link to this item: http://hdl.handle.net/2445/56084
Title: Synthesis of tripeptides for chelating metals involved in the aggregation of the ß-amyloid peptide responsible for Alzheimer disease
Other Titles: Síntesi de tripèptids quelants de metalls involucrats en l'agregació del pèptid ß-amiloide responsable de la malaltia de l’Alzheimer.
Author: Codina Francès, Maria del Mar
Director: Nicolás Galindo, Ernesto
Keywords: Pèptids
Quelants
Malaltia d'Alzheimer
Tesis
Peptides
Chelating agents
Alzheimer's disease
Theses
Issue Date: Jun-2014
Abstract: This work has been done in collaboration with the Bioinorganic Chemistry group of Inorganic Chemistry Department. This group is interested in chelating oligopeptides (about 3 or 4 amino acids) for metal ions such as copper and zinc, potential theranostic agents for Alzheimer disease. 1 Thereby we have synthesized peptides that contain at least two histidine residues (as metal-binding groups) and one natural or non-natural fluorescent amino acid (for detection purposes). We have used as fluorescent amino acids: tryptophan (W), tyrosine (T) and the non-natural amino acid Nε-(coumarin-3-ylcarbonyl)-L-Lysine (K(C)). The latter has been prepared in solution by reaction of 1H-benzotriazole with 2-oxo-2H-chromene-3-carboxylic acid to yield 3-(1Hbenzotriazol- 1-ylcarbonyl)-2H-chromen-2-one (52-60%) and the subsequent transformation of this intermediate to the final product by reaction with Fmoc-L-Lys-OH under basic condition (60- 85% yield). It has been characterized by proton nuclear magnetic resonance (1H-NMR). The synthesized peptides have been: histidine-alanine-histidine (HAH), histidine-alaninehistidine- tyrosine (HAHY), histidine-histidine-tryptophan (HHW), histidine-lysine(coumarin)- histidine (HK(C)H) and histidine-tryptophan-histidine (HWH) (Figure 1). HAH is the only one that hasn’t any fluorophore, but it has used as a blank to determine if fluorescent amino acid chelates the metal...
Note: Treballs Finals de Grau de Química, Facultat de Química, Universitat de Barcelona, Any: 2014, Tutor: Dr. Ernesto Nicolás Galindo
URI: http://hdl.handle.net/2445/56084
Appears in Collections:Treballs Finals de Grau (TFG) - Química

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