HPLC analysis of the organometallic modification of synthetic peptides: An evaluation of the indole and iClick conjugatins

Chueca Azlor, Sofía
Ulrich Schatzschneider (dir.)

Universidad de Zaragoza, CIEN, 2018

Graduado en Química

Abstract: Two different peptides were successfully synthesized, the sequences TFSDL and VLAKVAA via solid phase synthesis using in the first case a Fmoc-Leu-Wang resin and in the second case the attachment of the first amino acid to the Wang resin was done ourselves. The characterisation of both was done through mass spectrometry and HPLC, were good results were obtained. The first peptide obtained was coupled to a diene (2-carboxylic-3-trifluoromethyl-oxanorbornadiene) trying with 4 different coupling reactants which lead to the COMU/DIPEA ((1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate / Diisoprophylethylamine) as the chosen reagents for this reaction. In addition purification was needed, which was done by separating the different peaks that appeared in the HPLC measurement. A mass spectrum was obtained from each peak to characterise the product. The peptide with the masked alkyne attached onto it was used for iClick reaction with a ruthenium complex, (Ru(N3)(bpym)(p-cym)), which was measured for 6 days by HPLC, and a positive result from the coupling was obtained. It was performed two times because the first method could not separate the peaks of the ruthenium and the peptide. The second peptide synthesized (VLAKVAA) was used for the indole conjugation where all the peaks obtained in the mass spectrometer are related to the product, therefore it was a good method for the conjugation. Using the same procedure a metal indole conjugation was performed with the cymantrene (N-Cymantrenylmethyl-6-aminomethylindole) both at 50ºC and room temperature, but unfortunately the product was not formed because the cymantrene was not reactive enough. Another try was done with another metal indole (Mn(bpg6 aminomethyl)indol-k3N)(CO3)) but also did not work because it was too reactive that it formed a dimer with itself. In conclusion the goal of this research was archived, which is to obtain a metal peptide, although the metal indole conjugation did not work with both the metal indole used.

Tipo de Trabajo Académico: Trabajo Fin de Grado

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