C20-Otbu-glu-otbu
[CAS# 1119061-70-9]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: C20-Otbu-glu-otbu
• Synonyms: (4S)-5-[(2-methylpropan-2-yl)oxy]-4-[[20-[(2-methylpropan-2-yl)oxy]-20-oxoicosanoyl]amino]-5-oxopentanoic acid
• Molecular Formula: C₃₃H₆₁NO₇
• Molecular Weight: 583.84
• CAS Registry Number: 1119061-70-9
• SMILES: CC(C)(C)OC(=O)CCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CCC(=O)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 is a chemically designed molecule featuring a long-chain fatty acid derivative with two tert-butyl (Otbu) protected glutamic acid moieties. This structure integrates hydrophobic and hydrophilic components, making it useful in diverse applications ranging from materials science to pharmaceutical development.

The discovery of C20-Otbu-Glu-Otbu stemmed from the need for biocompatible and functionalized molecules for drug delivery and bioengineering. The long alkyl chain (C20) provides hydrophobic properties, improving its interaction with lipid-based systems such as liposomes or micelles. The glutamic acid units contribute potential sites for further chemical modifications or conjugation, while their Otbu protection ensures stability during synthetic processes.

The synthesis of C20-Otbu-Glu-Otbu generally starts with a fatty acid, such as eicosanoic acid, and involves stepwise coupling with glutamic acid derivatives. The tert-butyl groups are introduced to protect the carboxylic acid functionalities, ensuring selective reactivity and stability during intermediate stages. This synthesis typically employs high-purity reagents and catalysts, following strict protocols to yield the target compound with minimal impurities.

Applications of C20-Otbu-Glu-Otbu are diverse. In drug delivery systems, it acts as a hydrophobic anchor or spacer, facilitating the formation of amphiphilic assemblies like micelles or nanoparticles for encapsulating hydrophobic drugs. This enhances drug solubility, stability, and controlled release properties. In biomaterials development, the molecule is explored for use in hydrogels and surface coatings, improving cell adhesion and biocompatibility.

The compound’s modular structure also supports its use in designing prodrugs or functionalized polymers. By selectively deprotecting the Otbu groups, researchers can introduce active sites for further functionalization, such as conjugating bioactive molecules, enzymes, or targeting ligands. This versatility is particularly valuable in precision medicine and targeted therapies.

Ongoing studies are investigating its role in environmentally responsive systems, such as pH-sensitive drug carriers, and in designing hybrid materials that combine organic and inorganic components. Its amphiphilic properties and chemical flexibility position it as a valuable tool in advancing both therapeutic and material science innovations.

References

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