N3-D-Orn(Boc)-OH - CAS 2165877-62-1 Catalog number: BADC-01809

N3-D-Orn(Boc)-OH, a derivative of the amino acid ornithine with a Boc (tert-butoxycarbonyl) protecting group, is a valuable intermediate in peptide synthesis, particularly for incorporating D-amino acid residues into peptides. The Boc group is a commonly used protective group that shields the amino group from unwanted reactions during peptide elongation, enabling the precise synthesis of peptides with specific sequences. N3-D-Orn(Boc)-OH is particularly important in the synthesis of peptides that require enhanced stability, reduced enzymatic degradation, or specific biological activities, making it a versatile tool in drug development and bioengineering.

One of the main applications of N3-D-Orn(Boc)-OH is in the synthesis of D-amino acid-containing peptides. The use of D-amino acids, such as D-ornithine, in peptide synthesis increases the resistance of the peptides to proteases, preventing premature degradation in vivo. The incorporation of D-ornithine into peptides can also enhance their stability, bioavailability, and overall pharmacokinetic properties. The Boc group protects the amino group, ensuring the correct sequence formation during synthesis and allowing for efficient incorporation of D-amino acids without interference. This makes N3-D-Orn(Boc)-OH ideal for producing therapeutic peptides, such as antimicrobial agents, anticancer peptides, or hormone mimetics.

Another significant application of N3-D-Orn(Boc)-OH is in the preparation of peptide-drug conjugates (PDCs). The ornithine residue is an excellent site for conjugating peptides to various bioactive molecules, such as anticancer drugs, antibiotics, or diagnostic agents. The Boc protection ensures that the conjugation process is selective and controlled, preventing side reactions and ensuring the integrity of the peptide sequence. These conjugates offer improved targeting, reduced off-target effects, and enhanced therapeutic efficacy. N3-D-Orn(Boc)-OH-based conjugates are widely used in developing targeted therapies, particularly in cancer and infectious disease treatments.

N3-D-Orn(Boc)-OH is also used in the design of cyclic peptides and peptide mimetics. The incorporation of ornithine into cyclic peptides can improve the structural stability and bioactivity of the peptides. This makes N3-D-Orn(Boc)-OH an important building block for creating peptides that mimic the function of larger proteins, such as receptor-binding peptides or enzyme inhibitors. Additionally, the D-ornithine residue can influence the conformational properties of the peptide, making it useful in the design of peptide-based therapeutics with enhanced stability and selective binding.

Additionally, N3-D-Orn(Boc)-OH plays a critical role in the development of functionalized materials for drug delivery systems. The ornithine residue, which contains a primary amine group, is an ideal site for attaching drugs or targeting ligands to polymers or nanoparticles. The Boc group protects the amine during the polymerization or functionalization process, ensuring that the desired interactions occur after deprotection. This approach is particularly valuable in creating drug delivery systems that provide controlled release, targeted delivery, and reduced side effects in therapies such as cancer treatment or gene therapy.

Finally, N3-D-Orn(Boc)-OH is used in protein engineering and studies on protein-protein interactions. Incorporating D-ornithine residues into peptides can alter their folding, stability, and biological activity, providing insight into peptide function and helping researchers design more effective peptide-based drugs. The flexibility of N3-D-Orn(Boc)-OH makes it an important tool in the synthesis of bioactive peptides and in advancing peptide-based drug discovery.