Pal-Lys(Boc)-OH

Pal-Lys(Boc)-OH is a pivotal synthetic intermediate widely employed in the preparation of palmitoylated peptides and lipopeptide-based therapeutics. The compound features a lysine residue protected at the α-amino position with a Boc group and esterified at the side-chain carboxyl with a palmitoyl chain, creating a molecular scaffold that combines the hydrophilic character of the amino acid with the hydrophobic properties of the long-chain fatty acid. This unique amphiphilic structure makes Pal-Lys(Boc)-OH particularly valuable in the synthesis of palmitoyl tripeptide-5, a cosmetic and therapeutic peptide used in anti-aging formulations and wound healing applications. As a Boc-protected amino acid derivative, Pal-Lys(Boc)-OH is compatible with standard solid-phase peptide synthesis (SPPS) protocols, allowing researchers to incorporate the palmitoylated lysine residue at defined positions within the peptide sequence. The palmitoyl group of Pal-Lys(Boc)-OH enhances the membrane permeability and bioavailability of the resulting peptides, a property that has been successfully exploited in the design of cell-penetrating peptides and lipidated therapeutic agents. Furthermore, Pal-Lys(Boc)-OH serves as a key intermediate in the synthesis of various bioactive lipopeptides, including antimicrobial peptides and vaccine adjuvants, where the lipid moiety plays a critical role in immunological activity and target engagement.

Product Parameters

Quality Assurance at Cosperpharm

 Gas chromatography (GC) – purity ≥97.0%

 Non‑aqueous titration – purity ≥97.0%

 Refractive index – confirmatory analysis

 ¹H NMR – structural verification

lAppearance – colorless to light yellow to light orange clear liquid

A comprehensive COA, MSDS (with full GHS information), and certificate of origin accompany every shipment.

Product Advantages

    Dual-Functionalized Lysine Building Block

Pal-Lys(Boc)-OH features a lysine scaffold with two orthogonal modifications: a Boc-protected α-amino group for selective deprotection under acidic conditions, and a palmitoyl ester on the side-chain carboxyl for introducing lipophilic character. This dual-functionalized design allows Pal-Lys(Boc)-OH to serve as a "ready-to-use" building block for incorporating lipidated lysine residues at defined positions within peptide sequences.

    Enhanced Lipophilicity and Membrane Affinity

The palmitoyl (C16:0) moiety of Pal-Lys(Boc)-OH confers exceptional lipophilicity to the resulting peptides, significantly enhancing membrane permeability, cellular uptake, and bioavailability — properties that are critical for the development of cell-penetrating peptides, antimicrobial lipopeptides, and lipidated therapeutic agents.

 Orthogonal Protection Strategy

The Boc protecting group on Pal-Lys(Boc)-OH provides orthogonal protection that is selectively removable under mild acidic conditions (e.g., TFA in DCM), while the palmitoyl ester remains stable throughout standard SPPS protocols. This orthogonal protection strategy enables precise control over the final lipidation pattern of the target peptide.

 Key Intermediate for Palmitoyl Tripeptide-5

Pal-Lys(Boc)-OH is the essential building block for the synthesis of palmitoyl tripeptide-5 (Pal-Gly-His-Lys), a bioactive lipopeptide widely used in anti-aging cosmetic formulations and wound healing applications. The compound undergoes EDC/NHS activation to form the succinimidyl ester (Pal-Lys(Boc)-OSu), which is then coupled with dipeptide intermediates to furnish the final palmitoylated tripeptide.

 Broad Utility in Peptide Therapeutics

Beyond cosmetic applications, Pal-Lys(Boc)-OH serves as a versatile intermediate in the synthesis of various bioactive lipopeptides, including antimicrobial peptides, vaccine adjuvants, and cell-penetrating peptide conjugates, where the lipid moiety plays a critical role in target engagement and immunological activity.

FAQ

Q1: What is the CAS number of Pal-Lys(Boc)-OH?

A: The CAS number for Pal-Lys(Boc)-OH is 1621059-54-8. This specific CAS entry refers to the palmitoyl ester derivative of Boc-L-lysine. A related compound, Boc-L-Lys(Palm)-OH, is listed under CAS 59515-45-6 and may represent a different salt form or isomeric variant.

Q2: What is the difference between Pal-Lys(Boc)-OH and Boc-Lys(Palm)-OH?

A: Both names refer to the same general compound — a Boc-protected lysine with a palmitoyl ester modification. The naming convention varies by supplier and catalog. Pal-Lys(Boc)-OH (CAS 1621059-54-8) is the specific designation used in this product documentation, while Boc-L-Lys(Palm)-OH (CAS 59515-45-6) is a closely related compound that may differ in salt form or specific stereochemical configuration.

Contact Us

Need Pal-Lys(Boc)-OH for your lipopeptide synthesis project or cosmetic peptide manufacturing campaign? Cosperpharm is ready to support your research and production needs with high-quality building blocks and expert technical guidance. Reach out to our team today — we look forward to partnering with you.