C20-OTBU-GLU(OTBU)-AEEA-AEEA-OSU
[CAS# 1118767-17-1]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: C20-OTBU-GLU(OTBU)-AEEA-AEEA-OSU
• Synonyms: 19-((S)-1-tert-Butoxycarbonyl-3-{2-[2-({2-[2-(2,5-dioxopyrrolidin-1-yloxycarbonylmethoxy)ethoxy]ethylcarbamoyl}methoxy)ethoxy]ethylcarbamoyl}propylcarbamoyl)nonadecanoic acid tert-butyl ester; tert-butyl 20-[[(2S)-5-[2-[2-[2-[2-[2-[2-(2,5-dioxopyrrolidin-1-yl)oxy-2-oxoethoxy]ethoxy]ethylamino]-2-oxoethoxy]ethoxy]ethylamino]-1-[(2-methylpropan-2-yl)oxy]-1,5-dioxopentan-2-yl]amino]-20-oxoicosanoate
• Molecular Formula: C₄₉H₈₆N₄O₁₅
• Molecular Weight: 971.22
• CAS Registry Number: 1118767-17-1
• SMILES: CC(C)(C)OC(=O)CCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CCC(=O)NCCOCCOCC(=O)NCCOCCOCC(=O)ON1C(=O)CCC1=O)C(=O)OC(C)(C)C

Safety Data

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

Discovery and Applications

C20-OTBU-GLU(OTBU)-AEEA-AEEA-OSU represents a functionalized long-chain molecule designed for advanced applications in chemical biology and materials science. The molecule integrates a series of chemically distinct groups to provide versatile reactivity and compatibility in both biochemical and synthetic systems.

The molecule’s discovery is rooted in efforts to develop modular linkers and carriers for therapeutic and diagnostic platforms. Researchers sought a compound that combines hydrophobic and hydrophilic properties to enhance solubility and stability while incorporating functional groups for targeted chemical reactions. The long alkyl chain (C20) and tert-butyl (OTBU) protected moieties enhance structural integrity and allow selective deprotection for subsequent modification. AEEA (aminoethoxyethanol) groups add flexibility and hydrophilicity, while the OSU (N-hydroxysuccinimide) ester provides a reactive site for conjugation with amines.

The synthesis of C20-OTBU-GLU(OTBU)-AEEA-AEEA-OSU involves a series of protection, coupling, and activation steps. Typically, starting with a long-chain fatty acid, the carboxylic group is protected using tert-butyl esters to ensure stability. Subsequent steps involve introducing aminoethoxyethanol spacers and coupling them with activated succinimide esters. High-purity reagents and optimized reaction conditions are critical to obtaining the desired product with minimal byproducts.

Applications of this compound span a variety of fields. In drug delivery, it serves as a carrier or spacer in prodrug formulations and nanoparticle systems, allowing for controlled release and enhanced pharmacokinetics. The OSU group enables covalent bonding to biomolecules such as peptides, antibodies, or small molecules, facilitating the design of targeted therapeutic agents. Its structural flexibility also makes it valuable in creating multifunctional hydrogels and polymer networks for tissue engineering and regenerative medicine.

In materials science, the molecule’s amphiphilic nature supports its use in self-assembling systems, such as micelles or vesicles, for encapsulating hydrophobic drugs or imaging agents. Current studies are exploring its utility in the development of stimuli-responsive systems that adapt to environmental changes, such as pH or temperature.

Ongoing research focuses on optimizing its reactivity and exploring its potential in novel applications, including nucleic acid delivery and surface functionalization for biosensors. Its modular design provides a foundation for innovation in both biological and chemical contexts.

References

none