N3-L-Cys(Trt)-OH (CHA) - CAS 1286670-90-3 Catalog number: BADC-01723

N3-L-Cys(Trt)-OH (CHA) is a critical reagent in peptide synthesis, used to incorporate cysteine residues into peptides with enhanced stability and reactivity. The Trt (trityl) protection group on the cysteine thiol group is essential for controlling reactivity during solid-phase peptide synthesis (SPPS), as it prevents unwanted side reactions while still allowing for efficient peptide elongation. The N3-protection ensures that the cysteine residue can be introduced into peptide sequences without compromising the synthesis process, making it a versatile tool in peptide chemistry.

One of the key applications of N3-L-Cys(Trt)-OH (CHA) is in the creation of peptides with disulfide bonds. Cysteine residues are essential for forming these bonds, which are critical for stabilizing the three-dimensional structure of many bioactive peptides. The controlled introduction of cysteine using N3-L-Cys(Trt)-OH allows for the synthesis of cyclic peptides, which are more resistant to proteolysis and often have higher binding affinity for their target proteins. These cyclic peptides are used extensively in drug discovery, particularly for targeting protein-protein interactions and enzyme inhibition.

N3-L-Cys(Trt)-OH (CHA) is also employed in the synthesis of peptide-drug conjugates (PDCs), where cysteine is often used to link peptides with therapeutic agents such as cytotoxic drugs or targeting molecules. The thiol group on cysteine can undergo selective conjugation with various compounds, enabling the development of highly targeted therapies. This approach is particularly useful in oncology, where PDCs can deliver potent drugs directly to tumor cells, minimizing off-target effects and improving therapeutic efficacy.

Another significant application of N3-L-Cys(Trt)-OH (CHA) is in the development of peptides for biomedical and diagnostic applications. The thiol group of cysteine can be used for conjugating peptides to various diagnostic markers or imaging agents, allowing for targeted imaging in disease diagnosis. This is especially relevant in the development of molecular imaging probes for cancer, cardiovascular diseases, and neurodegenerative disorders. The controlled reactivity of the cysteine residue, protected by the Trt group, ensures that the conjugation process is precise and efficient.

Lastly, N3-L-Cys(Trt)-OH (CHA) is essential in the design of peptide-based vaccines and therapeutic peptides for immune modulation. Cysteine residues play an important role in protein structure and function, and their inclusion in vaccine peptides can help stabilize the vaccine’s conformation, ensuring a stronger and longer-lasting immune response. By incorporating N3-L-Cys(Trt)-OH, researchers can create peptides that are better suited for immune system activation and more effective as vaccines against infections, cancer, or autoimmune diseases.