Fmoc-L-Lys[C20-OtBu-Glu(OtBu)-AEEA-AEEA]-OH
[CAS# 2915356-76-0]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: Fmoc-L-Lys[C20-OtBu-Glu(OtBu)-AEEA-AEEA]-OH
• Synonyms: Tirzepatide sidechain
• Molecular Formula: C₆₆H₁₀₅N₅O₁₆
• Molecular Weight: 1224.56
• CAS Registry Number: 2915356-76-0
• SMILES: O=C(CC[C@@H](C(=O)OC(C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCC(=O)OC(C)(C)C)NCCOCCOCC(=O)NCCOCCOCC(=O)NCCCC[C@@H](C(=O)O)NC(=O)OCC1c2ccccc2-c2c1cccc2

Properties

• Density: 1.121±0.06 g/cm³, Calc.
• Boiling Point: 1225.0±65.0 °C, Calc.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P280-P305+P351+P338

Discovery and Applications

Fmoc-L-Lys[C20-OtBu-Glu(OtBu)-AEEA-AEEA]-OH is a highly specialized compound designed for applications in drug delivery and bioconjugation. Its discovery stems from the need for versatile and biocompatible molecules that can serve as intermediates in the synthesis of therapeutic agents or targeted drug delivery systems. The molecule incorporates multiple functional groups, including the Fmoc (fluorenylmethyloxycarbonyl) group, which protects the amino functionality of lysine during peptide synthesis, and a hydrophobic C20 alkyl chain to enhance lipophilicity. Additionally, the glutamic acid and AEEA (aminoethoxyethoxyacetate) units provide polar regions, making the molecule amphiphilic and suitable for a range of biological interactions.

The synthesis of Fmoc-L-Lys[C20-OtBu-Glu(OtBu)-AEEA-AEEA]-OH involves multi-step organic reactions, beginning with lysine derivatization. The Fmoc group is introduced to protect the lysine residue, followed by selective coupling with tert-butyl-protected glutamic acid and AEEA moieties. The hydrophobic C20 alkyl chain is then conjugated to the glutamic acid, providing the desired lipophilic properties. The final product is obtained through careful deprotection of specific groups while maintaining the integrity of the functionalized molecule.

Applications of this compound are centered on its potential in the development of targeted drug delivery systems. Its amphiphilic nature allows it to integrate into lipid-based carriers such as liposomes or micelles, which can encapsulate hydrophobic drugs. Additionally, the functional groups can be modified to attach targeting ligands or therapeutic molecules, making it ideal for creating personalized medicine platforms. The molecule's versatility also extends to its role in surface modification of nanoparticles, enhancing their stability and biocompatibility in vivo.

References

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