1-(tert-butyl) 5-(2,5-dioxopyrrolidin-1-yl) (16-(tert-butoxy)-16-oxohexadecanoyl)-L-glutamate
[CAS# 843666-26-2]

Identification

• Classification: Biochemical >> Common amino acids and protein drugs
• Name: 1-(tert-butyl) 5-(2,5-dioxopyrrolidin-1-yl) (16-(tert-butoxy)-16-oxohexadecanoyl)-L-glutamate
• Synonyms: 1-O-tert-butyl 5-O-(2,5-dioxopyrrolidin-1-yl) (2S)-2-[[16-[(2-methylpropan-2-yl)oxy]-16-oxohexadecanoyl]amino]pentanedioate
• Molecular Formula: C₃₃H₅₆N₂O₉
• Molecular Weight: 624.81
• CAS Registry Number: 843666-26-2
• SMILES: CC(C)(C)OC(=O)CCCCCCCCCCCCCCC(=O)N[C@@H](CCC(=O)ON1C(=O)CCC1=O)C(=O)OC(C)(C)C

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.489, Calc.^*
• Boiling Point: 420.2±28.0 °C (760 mmHg), Calc.^*
• Flash Point: 207.9±24.0 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovery and Applications

1-(tert-butyl) 5-(2,5-dioxopyrrolidin-1-yl) (16-(tert-butoxy)-16-oxohexadecanoyl)-L-glutamate is a complex synthetic compound that combines several functional groups and plays a significant role in pharmaceutical and biochemical applications. This compound features a tert-butyl group, which enhances its hydrophobicity, along with a glutamate moiety, which is an amino acid that is integral to various biological processes. The incorporation of a 2,5-dioxopyrrolidin-1-yl group serves as a versatile linker for bioconjugation, while the 16-(tert-butoxy)-16-oxohexadecanoyl component contributes a long-chain fatty acid structure.

The discovery of this compound stems from ongoing research into the synthesis of bioactive molecules and the development of drug delivery systems. Researchers sought to improve the stability and efficacy of therapeutic agents, particularly those targeting cellular pathways that involve membrane interactions. The unique structure of 1-(tert-butyl) 5-(2,5-dioxopyrrolidin-1-yl) (16-(tert-butoxy)-16-oxohexadecanoyl)-L-glutamate allows for the selective targeting of cellular membranes, making it an appealing candidate for various biomedical applications.

In terms of applications, this compound is particularly valuable in the realm of peptide synthesis and drug formulation. The presence of the 2,5-dioxopyrrolidin-1-yl group enables efficient coupling reactions with amine-containing molecules, facilitating the attachment of peptide sequences to lipid carriers or other drug delivery systems. This lipidation is crucial for enhancing the pharmacokinetic properties of peptides, allowing them to cross cell membranes more effectively and improve their overall bioavailability.

Furthermore, the compound's hydrophobic properties, conferred by the tert-butyl and hexadecanoyl components, contribute to its role in formulating lipid-based drug delivery systems. Such systems are designed to encapsulate hydrophobic drugs, protecting them from degradation and enhancing their absorption in biological environments. The incorporation of 1-(tert-butyl) 5-(2,5-dioxopyrrolidin-1-yl) (16-(tert-butoxy)-16-oxohexadecanoyl)-L-glutamate in these formulations can lead to improved therapeutic outcomes for various diseases, including cancer and metabolic disorders.

Additionally, the compound's ability to form stable covalent bonds with other biomolecules positions it as a valuable reagent in the field of bioconjugation. It allows for the creation of targeted drug conjugates, where the active drug is linked to a carrier that can recognize specific cell types, thereby minimizing off-target effects and enhancing therapeutic efficacy.

Research on 1-(tert-butyl) 5-(2,5-dioxopyrrolidin-1-yl) (16-(tert-butoxy)-16-oxohexadecanoyl)-L-glutamate continues to evolve, with ongoing studies focused on optimizing its synthesis and exploring new applications in drug delivery and biotechnology. Its multifunctional characteristics offer exciting possibilities in the development of novel therapeutic strategies aimed at improving patient outcomes in various medical conditions.

References

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