Fmoc-L-Lys[Oct-(otBu)-Glu-(otBu)-AEEA-AEEA]-OH
- Createtime: 2024-09-06
- Updatetime: 2024-09-06
Product Details
CAS |
1662688-20-1
|
PU |
99%
|
MF |
C64H101N5O16
|
Fmoc-L-Lys[Oct-(OtBu)-Glu-(OtBu)-AEEA-AEEA]-OH is a highly specialized and complex compound used in peptide synthesis, especially for constructing multifunctional peptides and peptide-lipid conjugates. The structure features several protective groups and functional components, making it a versatile building block for research in materials science, drug development, and bioconjugation.
Chemical Structure and Properties
Fmoc (Fluorenylmethyloxycarbonyl) Group: This protecting group is attached to the alpha-amino group of L-lysine, enabling controlled peptide synthesis. It prevents unwanted reactions during the assembly of the peptide chain and can be easily removed under mild basic conditions.
L-Lysine (L-Lys): L-Lysine is an essential amino acid with a reactive amine group on its side chain. In this compound, lysine serves as the backbone to which various functional components are attached.
Octanoic Acid (Oct): A fatty acid chain (C8) linked to the lysine side chain, providing hydrophobic properties. This lipid chain helps in improving membrane interaction and the bioavailability of peptides in biological systems.
OtBu (tert-Butyl Protecting Groups): The carboxyl groups of both glutamic acid (Glu) residues are protected by tert-butyl groups, preventing side reactions during peptide synthesis. These protecting groups can be easily removed under acidic conditions, allowing for the controlled release of carboxyl functionalities in later steps.
AEEA-AEEA: Aminoethoxyethanolamine (AEEA) units act as flexible spacers or linkers between different components. They increase the hydrophilicity of the molecule and improve solubility, enhancing its performance in bioconjugation or drug delivery applications.
Applications in Peptide and Drug Development
Peptide-Lipid Conjugates: The combination of lipid (Oct) and peptide components in this molecule is particularly useful for designing peptide-lipid conjugates. These conjugates are employed in drug delivery systems, where they improve the ability of peptides to interact with cell membranes, enhancing cellular uptake and bioavailability.
Multifunctional Peptide Synthesis: Fmoc-L-Lys[Oct-(OtBu)-Glu-(OtBu)-AEEA-AEEA]-OH is ideal for creating multifunctional peptides that require the attachment of lipophilic and hydrophilic components. The presence of AEEA spacers and multiple protective groups allows for controlled assembly of complex peptides with diverse functionalities.
Bioconjugation: The AEEA-AEEA spacer units provide flexibility and hydrophilicity, making this compound useful in bioconjugation—the process of attaching biologically active molecules to peptides, proteins, or surfaces. This application is essential in creating antibody-drug conjugates (ADCs), targeted therapies, or biosensors.
Controlled Drug Delivery: The molecule’s lipid chain (Oct) and flexible linkers (AEEA-AEEA) make it suitable for developing lipid-based drug delivery systems such as micelles or nanoparticles. These systems improve the solubility and stability of hydrophobic drugs, allowing for targeted drug release in therapeutic applications.
Importance in Research and Pharmaceutical Development
Fmoc-L-Lys[Oct-(OtBu)-Glu-(OtBu)-AEEA-AEEA]-OH is essential in pharmaceutical and biochemical research due to its versatility in modifying peptides and enhancing drug-like properties. Its ability to link lipid chains with peptide backbones opens up new avenues for developing targeted drug delivery systems, peptide-based therapeutics, and biomaterial design.
Conclusion
Fmoc-L-Lys[Oct-(OtBu)-Glu-(OtBu)-AEEA-AEEA]-OH is a complex and versatile compound used in advanced peptide synthesis. Its diverse functional components—lipid chains, spacers, and protective groups—make it highly valuable in drug development, targeted therapies, and biomaterials research. By facilitating the design of multifunctional peptides, this compound is crucial for innovations in pharmaceutical research and material science.