Peptides are potential therapeutic agents involved in a wide range of biological processes. In principle, rotaxanes can be used as novel prodrug delivery systems to overcome the problems of peptide degradation in vivo and their poor membrane transport permeability. The presence of the macrocycle around the peptide thread acts as a protective shield against peptidases and modifies its cell membrane transport characteristics. However, the classical ‘clipping’ method of rotaxane formation is mainly limited to dipeptide sequences since the presence of intramolecular hydrogen bonds in longer threads causes folding of the backbone, preventing good interactions with the precursor to the macrocycle. This thesis focused on the synthesis of short peptide rotaxane building blocks. Their elongation on both sides of the peptide backbone was then applied to the straightforward synthesis of oligopeptide [2] and [3]rotaxanes in very good yields.