Nicolás Galindo, ErnestoCodina Francès, Maria del Mar2014-07-212014-07-212014-06https://hdl.handle.net/2445/56084Treballs Finals de Grau de Química, Facultat de Química, Universitat de Barcelona, Any: 2014, Tutor: Dr. Ernesto Nicolás GalindoThis 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...63 p.application/pdfengcc-by-nc-nd (c) Codina Francès, 2014http://creativecommons.org/licenses/by-nc-nd/3.0/es/PèptidsQuelantsMalaltia d'AlzheimerTreballs de fi de grauPeptidesChelating agentsAlzheimer's diseaseBachelor's thesesinfo:eu-repo/semantics/bachelorThesisinfo:eu-repo/semantics/openAccess