N⁶-Cbz-L-lysine has various innovative applications in materials science, as follows:
For synthesizing high-performance hydrogels: N⁶-benzyloxycarbonyl-L-lysine-N-carboxyanhydride (L-Lys(Z)-NCA) can be used as a raw material to synthesize peptide-crosslinked hydrogels through reaction with an initiator. Despite having an ultra-low solid content, this hydrogel exhibits excellent mechanical properties such as high stretchability, high tensile strength, and exceptional resilience, making it applicable in fields like strain sensors.
As a gene carrier material: N⁶-Cbz-L-lysine can be used to prepare amphiphilic polypeptide gene carriers. For example, it can be polymerized to form poly(Cbz-L-lysine) segments, which are then combined with hydrophobic segments such as poly(L-leucine) to form block copolymers. These copolymers can compress plasmid DNA and assemble into particles with a diameter of less than 100 nm, delivering them into cells with the advantages of high cell transfection efficiency and low cytotoxicity.
Preparing metal chelates for material modification: N⁶-Cbz-L-lysine can serve as an intermediate for producing N,N-bis(carboxymethyl)-L-lysine, whose downstream products can be used to prepare metal chelates. These metal chelates can modify ordered mesoporous silica, immobilizing proteins within nanopores to enhance protein stability. They can also effectively complex with His-tags, facilitating the purification of proteins from crude cell lysates. Additionally, they can be combined with metal nanoparticles to construct artificial enzymes, improving the activity of antibiotics in killing enclosed bacteria, among other applications.
As an intermediate for synthesizing peptide-based materials: N⁶-Cbz-L-lysine benzyl ester hydrochloride is an important raw material for synthesizing complex peptides and protein drugs. Its benzyloxycarbonyl (Cbz) group can protect the α-amino group of lysine, and the benzyl ester can protect the carboxyl group, allowing lysine to be introduced at specific positions in the peptide chain while avoiding unnecessary side reactions. The benzyl ester group can also be cleaved under mild conditions, facilitating further extension of the peptide chain.
For preparing amino acid derivative corrosion inhibitors: Using N⁶-Cbz-L-lysine as a raw material, a series of amino acid derivatives (such as 2-amino-6-(2-hydroxybenzamido)hexanoic acid) can be synthesized. These derivatives can act as corrosion inhibitors for low-carbon steel, protecting it in environments such as 1M HCl solution and reducing corrosion.
