Fmoc-L-Lys[Oct-(otBu)-Glu-(otBu)-AEEA-AEEA]-OH
[CAS# 1662688-20-1]

Identification

• Classification: Biochemical >> Peptide
• Name: Fmoc-L-Lys[Oct-(otBu)-Glu-(otBu)-AEEA-AEEA]-OH
• Synonyms: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[2-[2-[2-[[2-[2-[2-[[(4S)-5-[(2-methylpropan-2-yl)oxy]-4-[[18-[(2-methylpropan-2-yl)oxy]-18-oxooctadecanoyl]amino]-5-oxopentanoyl]amino]ethoxy]ethoxy]acetyl]amino]ethoxy]ethoxy]acetyl]amino]hexanoic acid
• Molecular Formula: C₆₄H₁₀₁N₅O₁₆
• Molecular Weight: 1196.51
• CAS Registry Number: 1662688-20-1
• EC Number: 892-611-1
• SMILES: CC(C)(C)OC(=O)CCCCCCCCCCCCCCCCC(=O)N[C@@H](CCC(=O)NCCOCCOCC(=O)NCCOCCOCC(=O)NCCCC[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)C(=O)OC(C)(C)C

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.520, Calc.^*
• Boiling Point: 1215.5±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 688.9±34.3 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

Fmoc-L-Lys[Oct-(otBu)-Glu-(otBu)-AEEA-AEEA]-OH is a highly specialized compound for peptide synthesis and bioconjugation. It was developed as a result of advances in solid phase peptide synthesis (SPPS) and bioconjugation techniques. The compound utilizes Fmoc (9-fluorenylmethoxycarbonyl) to protect amino acids during peptide synthesis, a strategy that became widely adopted in the 1980s due to its mild deprotection conditions.

The Fmoc group in the compound protects the N-terminal amine of the lysine residue and is removable under alkaline conditions. Lysine serves as a backbone for further functionalization. Attached to the lysine is an octanoyl group. Glutamic acid with a tert-butyl ester protecting group on the side chain. Two 2-(2-aminoethoxy)ethanol units provide flexibility and spacing between the functional groups. The compound is a white to off-white powder that is soluble in organic solvents such as dimethylformamide (DMF) and dimethyl sulfoxide (DMSO).

This compound plays an important role in SPPS and can be used to assemble complex peptides with multiple functions. Fmoc protection allows stepwise extension of the peptide chain, while the protecting groups on lysine and glutamic acid prevent unwanted side reactions. Fmoc-L-Lys[Oct-(otBu)-Glu-(otBu)-AEEA-AEEA]-OH is used to create peptide conjugates that incorporate lipophilic moieties or other functional groups, thereby enhancing the performance of the peptide for therapeutic or diagnostic applications.

The AEEA (2-(2-aminoethoxy)ethanol) spacer provides flexibility for attaching peptides to proteins or other biomolecules, facilitating the design of labeled proteins for research and diagnostic purposes. This compound is used to create drug delivery systems by linking bioactive peptides to carriers or targeting moieties. Protecting groups and linkers allow precise control of drug release and targeting.

Fmoc-L-Lys[Oct-(otBu)-Glu-(otBu)-AEEA-AEEA]-OH is used to modify surfaces, such as hydrogels or nanoparticles, to impart specific biological functions or interactions. This modification is valuable in tissue engineering and the development of biosensors. The compound is able to combine hydrophobic and hydrophilic elements, suitable for creating hydrogels with customized properties for cell culture, drug delivery or wound healing.

The compound facilitates the synthesis of peptide-based therapeutics with enhanced stability and bioavailability. The manufacture of multivalent peptides can improve binding affinity and specificity to biological targets and is of great value in cancer treatment, antiviral drugs and immunotherapy. The combination of Fmoc groups and linkers allows the creation of peptides that can target specific cells or tissues, thereby improving efficacy and reducing side effects of treatment.

References

none