Sinteza 4-boronofenilalanina za sintezo peptidov ter spajanje po Suzukiju

Šarić, Lea (author), Gazvoda, Martin (mentor)

V diplomskem delu smo preučevali Suzuki-Miyaura reakcijo za funkcionalizacijo peptidov v vodnem mediju z uporabo vodotopnega paladijevega katalizatorja Py-tzNHC. Sintetizirali smo 4-jodo-L-fenilalanin, ga zaščitili s Fmoc zaščitno skupino ter vključili v peptidno zaporedje s sintezo peptidov na trdnem nosilcu (SPPS). Proučevali smo vpliv različnih reakcijskih pogojev, predvsem količine katalizatorja, pH, reakcijskega časa in izbire paladijevega katalizatorja, na uspešnost Suzuki-Miyaura sklopitve. Potek reakcij in nastanek produktov smo spremljali z LC-Ms analizo. Na podlagi rezultatov smo izbrali ustrezne reakcijske pogoje ter jih uporabili pri zahtevnejših peptidnih sistemih. Uspešno smo izvedli tudi Suzuki-Miyaura sklopitev dveh peptidov, kar smo potrdili z LC-MS analizo.

• Language: Slovenian
• Keywords: Suzuki-Miyaura reakcija, SPPS, jodofenilalanin, paladijev katalizator, funkcionalizacija peptidov
• Work type: Bachelor thesis/paper
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2026
• PID: 20.500.12556/RUL-186935
• Publication date in RUL: 07.09.2026

Secondary language

• Language: English
• Title: Synthesis of 4-boronophenylalanine for peptide synthesis and Suzuki coupling

Abstract

In this bachelor's thesis, we investigated the Suzuki-Miyaura reaction for the functionalization of peptides in an aqueous medium using the water-soluble palladium catalyst Py-tzNHC. 4-iodo-L-phenylalanine was synthesized, protected with an Fmoc protecting group and incorporated into a peptide sequence by solid-phase peptide synthesis (SPPS). The effects of different reaction conditions, particularly catalyst loading, pH. reaction time and the choice of palladium catalyst, on the efficiency of the Suzuki-Miyaura coupling were investigated. The progress of the reactions and product formation were monitored by LC-MS analysis. Based on the obtained results, suitable reaction conditions were selected and subsequently applied to more complex peptide systems. A Suzuki-Miya ura coupling between two peptides was also successfully performed and confirmed by LC-MS analysis.

• Keywords: Suzuki-Miyaura reaction, SPPS, iodophenylalanine, palladium catalyst, peptide functionalization