Synthesis of biodegradable and photocurable glycine based amino acid phosphoramidates for biomedical applications

Tissue engineering combines various fields in medicine in an interdisciplinary manner to restore, maintain, or improve tissue functions. Due to the aging population and the complexity of potential defects, bone, ligament and tendon reconstruction are areas of rising importance. Although there are various approaches, ranging from bioactive ceramics, metals, to synthetic and natural polymers, the choice of material remains a long-term challenge, since each of these materials, also posses disadvantages depending on the application. A promising solution is provided by amino acid phosphoramidates. These phosphoramidates posess at least one amino acid group and functional groups for polymerization at the end of each sidechain. Their structure is easily modified and can be tailored for specific applications by changing the amino acid or polymerizable functional group. This makes amino acid phosphoramidates particularly attractive for using additive manufacturing methods as the chosen process methods. Especially in the field of light-curing 3D printing technologies, phosphoramidates offer opportunities to create excellent and precise 3D models. Additionally, amino acid phosphoramidates are characterized by their variable degradation rate at a neutral pH-value, which leads to non-toxic phosphates. Due to these and other advantages, this thesis aims to synthesize three different amino acid phosphoramidates and expand their thermo-mechanical properties and degradation behaviour in various polymer formulations.