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Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/56084
Synthesis of tripeptides for chelating metals involved in the aggregation of the ß-amyloid peptide responsible for Alzheimer disease
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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...
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Treballs Finals de Grau de Química, Facultat de Química, Universitat de Barcelona, Any: 2014, Tutor: Dr. Ernesto Nicolás Galindo
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CODINA FRANCÈS, Maria del mar. Synthesis of tripeptides for chelating metals involved in the aggregation of the ß-amyloid peptide responsible for Alzheimer disease. [consulta: 21 de gener de 2026]. [Disponible a: https://hdl.handle.net/2445/56084]