N2-(1-Oxotetradecyl)-L-lysyl-L-leucyl-L-alanyl-L-lysyl-L-lysinamide
[CAS# 959610-30-1]

Identification

• Classification: Biochemical >> Peptide
• Name: N2-(1-Oxotetradecyl)-L-lysyl-L-leucyl-L-alanyl-L-lysyl-L-lysinamide
• Synonyms: N-[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1,6-diamino-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]tetradecanamide
• Molecular Formula: C₄₁H₈₁N₉O₆
• Molecular Weight: 796.14
• Protein Sequence: KLAKK
• CAS Registry Number: 959610-30-1
• SMILES: CCCCCCCCCCCCCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N

Properties

• Solubility: Very slightly soluble (0.26 g/L) (25 °C), Calc.^*
• Density: 1.062±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 1071.6±65.0 °C 760 mmHg (Calc.)^*
• Flash point: 601.9±34.3 °C (Calc.)^*
• Index of refraction: 1.51 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

N2-(1-Oxotetradecyl)-L-lysyl-L-leucyl-L-alanyl-L-lysyl-L-lysinamide is a synthetic pentapeptide designed with a lipid modification at the N-terminal lysine and amidation at the C-terminal lysine. The incorporation of a 1-oxotetradecyl group, a long-chain fatty acid, imparts amphiphilic properties that enhance the peptide’s interaction with lipid membranes and contribute to improved stability against proteolytic degradation. Such structural modifications are widely used in peptide chemistry to increase bioavailability, facilitate cellular uptake, and modulate biological activity.

The development of lipidated peptides like this pentapeptide arose from advances in peptide synthesis and the exploration of peptide therapeutics in the late twentieth century. Researchers discovered that conjugation of fatty acyl chains to short peptide sequences could significantly alter their physicochemical properties, including solubility, membrane affinity, and resistance to enzymatic cleavage. By combining these modifications with carefully chosen amino acid sequences, chemists created compounds capable of mimicking or modulating biological processes with enhanced stability and specificity.

Structurally, this pentapeptide contains lysine residues with positively charged side chains, leucine and alanine residues providing hydrophobicity and conformational flexibility, and a lipidated N-terminal lysine that increases membrane affinity. The C-terminal amidation of lysine protects the peptide from carboxypeptidase activity and contributes to the overall stability. The sequence design balances hydrophobic and hydrophilic interactions, making it suitable for studies of peptide–membrane interactions and receptor engagement. The presence of multiple lysine residues also facilitates electrostatic interactions with negatively charged surfaces, including bacterial membranes and cellular membranes.

The applications of N2-(1-Oxotetradecyl)-L-lysyl-L-leucyl-L-alanyl-L-lysyl-L-lysinamide are primarily in biochemical research and experimental therapeutics. Lipidated peptides of this type have been investigated as potential antimicrobial agents because their amphiphilic character allows them to interact with and disrupt microbial membranes. They are also used as model compounds in studies of peptide–lipid interactions, helping to elucidate the mechanisms by which short amphiphilic peptides partition into membranes, form transient pores, or trigger signaling pathways.

In addition to functional studies, the peptide serves as a reference standard in analytical chemistry. Its defined sequence and lipid modification allow precise characterization using chromatographic and mass spectrometric techniques. The presence of the long-chain acyl group influences retention behavior in liquid chromatography and can be used to study partitioning or membrane association in experimental systems.

Although this pentapeptide is not used therapeutically on a large scale, it exemplifies the strategies employed in peptide design for research and potential biomedical applications. Its combination of N-terminal lipidation, strategically placed hydrophobic and basic residues, and C-terminal amidation illustrates how chemical modifications can be used to tune the physicochemical and biological properties of short peptides.

Overall, N2-(1-Oxotetradecyl)-L-lysyl-L-leucyl-L-alanyl-L-lysyl-L-lysinamide demonstrates the integration of amino acid sequence design and lipid modification to produce a stable, functional molecule. Its structural characteristics, including amphiphilicity, protease resistance, and potential membrane interaction, make it a valuable tool for studying peptide function, membrane activity, and structure–activity relationships in peptide chemistry and molecular biology research.

References

2025. Stem cell exosome anti-hair loss and hair growth compound and preparation method thereof. CN Patent.
URL: CN-119112938-A

2025. Hair-fixing, hair-losing-preventing and hair-blackening compound-effect liposome and preparation method thereof. CN Patent.
URL: CN-119345047-A