N3-D-Lys(Fmoc)-OH - CAS 1994300-35-4 Catalog number: BADC-01794

N3-D-Lys(Fmoc)-OH, a derivative of L-lysine with a Fmoc (9-fluorenylmethyloxycarbonyl) protective group, is a critical intermediate in peptide synthesis, particularly for peptides incorporating D-amino acid residues. The Fmoc group is widely used in solid-phase peptide synthesis (SPPS) as a protecting group for the amino group, allowing selective deprotection and extension of peptide chains. N3-D-Lys(Fmoc)-OH is specifically useful for creating peptides with altered stability, improved bioavailability, or designed bioactivity, making it a valuable tool in therapeutic peptide development and drug discovery.

One of the main applications of N3-D-Lys(Fmoc)-OH is in the synthesis of D-amino acid-containing peptides. The incorporation of D-amino acids, such as D-lysine, into peptides can enhance their stability by preventing enzymatic degradation, particularly by proteases. This characteristic is valuable for designing peptides with prolonged half-lives in biological systems. The Fmoc group protects the amino group during peptide elongation, ensuring that only the desired reactions occur, which is crucial in synthesizing complex peptide sequences with high purity and specificity. This feature is important for developing therapeutic peptides for cancer treatment, antimicrobial therapies, and other medical applications.

Another significant application of N3-D-Lys(Fmoc)-OH is in the creation of peptide conjugates. The lysine side chain can be conjugated to various bioactive molecules, such as drugs, targeting agents, or diagnostic probes. The Fmoc-protected N3-D-Lys(Fmoc)-OH can be used to facilitate the conjugation process by selectively protecting the amine group and ensuring the integrity of the peptide chain. These conjugates are important for developing targeted therapies, including peptide-drug conjugates (PDCs) and antibody-drug conjugates (ADCs), which enhance drug specificity, reduce side effects, and improve therapeutic outcomes in diseases such as cancer.

N3-D-Lys(Fmoc)-OH is also widely used in the design of peptide mimetics. Peptide mimetics are small molecules that mimic the biological activity of natural peptides but often offer improved stability, oral bioavailability, and pharmacokinetic properties. By incorporating N3-D-Lys(Fmoc)-OH into small-molecule scaffolds or cyclic peptides, researchers can develop mimetics that are useful for inhibiting protein-protein interactions, enzymes, or receptors. This makes N3-D-Lys(Fmoc)-OH an essential component in drug discovery, particularly for designing potent inhibitors for various biological targets.

Additionally, N3-D-Lys(Fmoc)-OH plays a role in the development of bioactive materials, such as functionalized polymers or hydrogels for drug delivery applications. The lysine residue allows for the attachment of various functional groups, enhancing the material’s bioactivity and interaction with cells. The Fmoc group ensures the integrity of the polymer during synthesis and can be removed under mild conditions to allow further functionalization. These materials are particularly useful in the creation of controlled release systems for drugs, enabling targeted delivery and minimizing systemic toxicity.