N⁶-Cbz-L-lysine has various applications in the preparation of biomaterials, mainly reflected in the following aspects:
Used in the preparation of antibacterial and anticancer materials: It can be used as a raw material to synthesize amphiphilic short peptide-grafted hyperbranched polymers. These polymers carry a large number of positive charges and can adsorb onto the negatively charged cell membranes of tumor cells and bacteria through electrostatic interactions. Subsequently, the amphiphilic short peptides insert into the cell membranes to form transmembrane channels, causing the contents of tumors and bacteria to flow out, thereby achieving antibacterial and anticancer activities.
Involvement in polylysine synthesis: N⁶-Cbz-L-lysine can be used to prepare polylysine, a synthetic basic poly-α-amino acid. Studies have found that polylysine can inhibit fungal infection of sweet potatoes, reduce fungal penetration, promote callus formation, and to a certain extent inhibit the infection of tomato cuttings by pathogens. Although it has certain toxicity to plants, it is of significance for exploring antifungal and other functional materials in the research and development of related biomaterials.
Assisting in the synthesis of peptide and protein drugs: N⁶-Cbz-L-lysine benzyl ester hydrochloride, a common derivative, can be used in the synthesis of complex peptide and protein drugs. Due to its ability to form stable complexes with metal ions, it can also be used in metal ion complexation research and in the preparation of pseudopeptides as thrombolytic agents, playing a role in the interdisciplinary field of biomaterials and drug research and development.
Preparing self-assembling peptide probes: It can participate in the preparation of self-assembling peptide probes that recognize 6xHis-tagged proteins. Relevant small-molecule peptide compounds can self-assemble into nano hydrogels under the catalysis of alkaline phosphatase in the presence of divalent metal ions. These nano hydrogels have good biocompatibility and favorable three-dimensional morphology, can easily enter tumor cells, and can be used to indicate the subcellular distribution of recombinant histidine target proteins in cells, showing broad application prospects in biomedicine and biomaterials.
Synthesizing hypoxia-responsive drug delivery micelles: It can be used to synthesize hypoxia-responsive polymers. For example, lys(Z)-NCA is synthesized with triphosgene using the Fuchs-Farthing method, and then further involved in reactions to form polyethylene glycol-polylysine-paclitaxel-polyphenylalanine triblock polymers. Chemotherapeutic drug paclitaxel can be coupled to lysine amino groups through disulfide bonds to prepare hypoxia-responsive drug delivery micelles, which can encapsulate gemcitabine prodrugs, etc., to achieve targeted drug delivery, and have important value in biomaterial applications such as tumor therapy.
Serving as an amino-protecting group: N⁶-Cbz-L-lysine can protect the amino group on lysine, preventing it from participating in non-specific reactions during peptide or protein synthesis. When needed, the protecting group can be removed, thereby precisely controlling reaction sites and product structures, which is crucial for the preparation of biomaterials with specific structures and functions.
