1301706-55-7

Basic information

• Product Name: FMOC-LYS(PALMITOYL)-OH
• Synonyms: N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-N-EPSILON-PALMITOYL-L-LYSINE;N-ALPHA-FMOC-N-EPSILON-PALMITOYL-L-LYSINE;FMOC-L-LYS(PALM)-OH;FMOC-LYSINE(PALMITOYL)-OH;FMOC-LYS(PAL)-OH;FMOC-N-EPSILON-PALMITOYL-L-LYSINE;Palmitoyl lysine;Nα-Fmoc-Nε-Palmitoyl-D-Lysine≥ 99% (HPLC)
• CAS NO: 1301706-55-7
• Molecular Formula: C37H54N2O5
• Molecular Weight: 606.84
• Mol File: 1301706-55-7.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -15°C
• CAS DataBase Reference: FMOC-LYS(PALMITOYL)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-LYS(PALMITOYL)-OH(1301706-55-7)
• EPA Substance Registry System: FMOC-LYS(PALMITOYL)-OH(1301706-55-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1301706-55-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
FMOC-LYS(PALMITOYL)-OH is used as a building block in the synthesis of lipidated peptides for enhancing their cellular permeability and metabolic stability. This application is particularly relevant in the development of drugs that require efficient delivery across cellular barriers and improved pharmacokinetic properties.
Used in Research and Development:
In the field of research and development, FMOC-LYS(PALMITOYL)-OH serves as a valuable tool for studying the effects of lipidation on peptide behavior. It can be used to investigate the mechanisms by which lipidated peptides interact with biological membranes and their potential applications in drug delivery and targeting.
Used in Peptide Synthesis:
FMOC-LYS(PALMITOYL)-OH is used as a protected amino acid in solid phase peptide synthesis. The 9-fluorenylmethoxycarbonyl (Fmoc) group provides a convenient method for the stepwise assembly of peptides, allowing for the controlled addition of amino acids and the subsequent removal of protecting groups during the synthesis process.

Upstream product

• 105047-45-8 Fmoc-Lys-OH 
• 139122-42-2 palmitic acid pentafluorophenyl ester 
• 71989-26-9 Fmoc-Lys(tert-butoxycarbonyl) 
• 57-10-3 1-hexadecylcarboxylic acid 
• 14464-31-4 palmitic acid N-succinimide ester 

Relevant articles and documents

Palmitoyl derivatives of GpMBP epitopes: T-cell response and peptidases susceptibility

We report for the first time the immunoadjuvant effects of lipoconjugation of peptide antigens in an in vitro system by using CD4+ T-cells. The lipopeptides obtained by conjugating a palmitoyl moiety at the Nα-terminal of Gln74 or at

Cell adhesion through clustered ligand on fluid supported lipid bilayers

The quartz crystal microbalance technique with dissipation monitoring and the complementary optical microscopy technique were used for monitoring cell adhesion on an RGD-functionalized supported lipid bilayer. A critical interligand RGD spacing of nearly 80 nm was estimated for cell adhesion when an RGD spacing of 10 nm was necessary to observe flattened cells on a fluid surface.

Co-liposomes comprising a lipidated multivalent RGD-peptide and a cationic gemini cholesterol induce selective gene transfection in αvβ3 and αvβ5 integrin receptor-rich cancer cells

The αvβ3 and αvβ5 integrins, transmembrane glycoprotein receptors, are over-expressed in numerous tumors and in endothelial cells that constitute tumor blood vessels. As this protein selectively binds to the Arg-Gly-Asp (RGD) sequence containing peptides, it is an attractive way to target tumors. Herein we have developed novel formulations for integrin mediated selective gene delivery. These formulations are composed of a novel palmitoylated tetrameric RGD containing scaffold (named RAFT-RGD), cationic gemini cholesterol (GL5) and a natural helper lipid 1,2-dioleoyl-l-α- glycero-3-phosphatidylethanolamine (DOPE). We have optimized a co-liposomal formulation to introduce the multivalent RGD-containing macromolecule in GL5: DOPE (GL5D) mixture to produce GL5D-RGD. We have unambiguously shown the selectivity of these formulations towards cancer cells that over express αvβ3 and αvβ5 integrins. Two reporter plasmids, pEGFP-C3 and PGL-3, were employed for the transfection experiments and it was shown that GL5D-RGD liposomes increased exclusively the transfection in αvβ3 and αvβ5-overexpressing HeLa cells. This journal is the Partner Organisations 2014.