Syntheses and Evaluation of Peptoids as Bioinert Coatings for Nanoparticles

Polymers of N-substituted glycine (NSG) or as they are also called, peptoids, have shown potential in biomedical applications due to proteolytic resistance, among other interesting properties. In this thesis project, two synthetic routes have been performed and evaluated to achieve a better understanding of large-scale syntheses of peptoids as a bioinert coating for nanoparticles. The primary focus has been on a solution-phase synthesis where the monomer, N-(3,6,9-trioxadecyl)glycine, has been synthesized via an oxidation of a primary alcohol to aldehyde followed by reductive amination. A “submonomer” approach, where the peptoid is grown on a resin in an iterative process of nucleophilic displacements and acylations, has also been performed but with a 3-methoxypropyl side chain.Begränsningar med polyetylenglykol (PEG) som ytbeläggningen av proteiner och nanopartiklar i biologiska tillämpningar, har ökat intresset för peptoider. Peptoider har framställts med både en fastfassyntes och en syntes i lösningsmedel. Vad är mest lämpligt för storskalig framställning