(S)-2-(19-tert-butoxycarbonylnonadecanoylamino)pentanedioic acid 1-tert-butyl ester 5-(2,5-dioxopyrrolidin-1-yl) ester
[CAS# 1119061-72-1]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: (S)-2-(19-tert-butoxycarbonylnonadecanoylamino)pentanedioic acid 1-tert-butyl ester 5-(2,5-dioxopyrrolidin-1-yl) ester
• Synonyms: 1-O-tert-butyl 5-O-(2,5-dioxopyrrolidin-1-yl) (2S)-2-[[20-[(2-methylpropan-2-yl)oxy]-20-oxoicosanoyl]amino]pentanedioate
• Molecular Formula: C₃₇H₆₄N₂O₉
• Molecular Weight: 680.91
• CAS Registry Number: 1119061-72-1
• SMILES: CC(C)(C)OC(=O)CCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CCC(=O)ON1C(=O)CCC1=O)C(=O)OC(C)(C)C

Discovory and Applicatios

(S)-2-(19-tert-Butoxycarbonylnonadecanoylamino)pentanedioic acid 1-tert-butyl ester 5-(2,5-dioxopyrrolidin-1-yl) ester is a specialized molecule designed for applications in materials science and bioconjugation chemistry. This compound combines a long-chain fatty acid with a protected glutamic acid derivative, making it highly adaptable for various chemical modifications and applications.

The discovery of this compound aligns with efforts to create multifunctional molecules for biomedical and material sciences. Its structure includes a nonadecanoic acid chain providing hydrophobic properties, a glutamic acid core offering reactive sites for bioconjugation, and tert-butyl ester groups that ensure stability during synthesis. Additionally, the inclusion of a succinimidyl ester group at the terminal position enhances its utility for coupling with amines, a common feature in peptides and proteins.

The synthesis of this compound involves sequential protection and coupling reactions. The long-chain fatty acid is first functionalized with a carbamate group for stability and subsequently attached to the glutamic acid backbone. The tert-butyl esters are introduced to protect the carboxylic acid groups, and the succinimidyl ester is added as the final reactive site. Each step typically employs mild conditions to preserve the integrity of sensitive functional groups.

Applications of this compound are broad and versatile. It is widely used in the preparation of lipophilic prodrugs and targeted delivery systems. Its amphiphilic nature allows for incorporation into lipid-based carriers such as micelles and nanoparticles, improving the solubility and bioavailability of hydrophobic drugs. The succinimidyl ester functionality enables rapid conjugation with biomolecules, making it a valuable tool in protein and peptide labeling.

In materials science, this compound contributes to the design of hybrid materials with tailored surface properties. For example, its incorporation into polymers can enhance compatibility with biological systems, making it suitable for use in implants and coatings. The molecule also shows potential in the development of stimuli-responsive systems, where environmental triggers such as pH can regulate drug release.

This compound continues to be explored for its applications in advancing drug delivery, diagnostic systems, and biocompatible materials. Its multifunctional design ensures that it remains a cornerstone for innovative solutions in both therapeutic and material science disciplines.