Fmoc-Lys(Pal-Glu-OtBu)-OH
[CAS# 1491158-62-3]

Identification

• Classification: Biochemical >> Peptide
• Name: Fmoc-Lys(Pal-Glu-OtBu)-OH
• Synonyms: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[(4S)-4-(hexadecanoylamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoyl]amino]hexanoic acid
• Molecular Formula: C₄₆H₆₉N₃O₈
• Molecular Weight: 792.06
• CAS Registry Number: 1491158-62-3
• SMILES: CCCCCCCCCCCCCCCC(=O)N[C@@H](CCC(=O)NCCCC[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)C(=O)OC(C)(C)C

Properties

• Solubility: Insoluble (2.5E^-6 g/L) (25 ºC), Calc.^*
• Density: 1.099±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

Safety Data

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

Discovory and Applicatios

Fmoc-Lys(Pal-Glu-OtBu)-OH is a specialized amino acid derivative that plays a crucial role in the field of peptide synthesis and medicinal chemistry. This compound is characterized by the presence of a fluorinated methoxycarbonyl (Fmoc) protective group attached to a lysine residue, which is further modified by a palmitoyl (Pal) and a protected glutamic acid (Glu) moiety. Its unique structure enables it to function effectively as a building block in the synthesis of biologically active peptides and proteins.

The discovery of Fmoc-Lys(Pal-Glu-OtBu)-OH can be traced back to the development of Fmoc chemistry, a widely used approach in solid-phase peptide synthesis (SPPS). The Fmoc group provides a convenient means for the protection and deprotection of amino acids during the peptide assembly process. This methodology emerged in the late 20th century as a significant advancement in peptide synthesis, facilitating the production of complex peptides with high purity and yield.

In the context of peptide synthesis, Fmoc-Lys(Pal-Glu-OtBu)-OH serves multiple functions. The lysine residue is a key amino acid known for its role in providing positive charge and site-specific modification within peptides. The incorporation of the palmitoyl group enhances the hydrophobicity of the peptide, which can influence its biological activity and membrane permeability. Furthermore, the glutamic acid moiety, when protected as the O-benzyl ester (OtBu), allows for controlled release and activation in biological environments.

Fmoc-Lys(Pal-Glu-OtBu)-OH has found applications in the design and synthesis of peptide-based therapeutics, including those targeting cancer, inflammation, and metabolic disorders. By using this compound as a building block, researchers can create peptides that exhibit specific biological activities, improved stability, and enhanced delivery characteristics. Its versatility also extends to the development of peptide-based drug conjugates, where it serves as a linker between active pharmaceutical ingredients and targeting moieties.

Moreover, this compound's role in structure-activity relationship (SAR) studies enables researchers to evaluate the effects of various modifications on peptide function, aiding in the rational design of novel therapeutic agents. The ability to fine-tune the physicochemical properties of peptides through the incorporation of Fmoc-Lys(Pal-Glu-OtBu)-OH contributes significantly to advances in drug development and personalized medicine.

In terms of safety, Fmoc-Lys(Pal-Glu-OtBu)-OH should be handled with care in laboratory settings, following standard protocols for chemical safety. Proper protective equipment, including gloves and safety goggles, is recommended to minimize exposure during synthesis and handling.

In summary, Fmoc-Lys(Pal-Glu-OtBu)-OH represents an important advancement in the field of peptide chemistry. Its discovery has facilitated the synthesis of complex peptides with potential therapeutic applications, making it a valuable tool for researchers in medicinal chemistry and drug development.