(S)-22-(tert-Butoxycarbonyl)-43,43-dimethyl-10,19,24,41-tetraoxo-3,6,12,15,42-pentaoxa-9,18,23-triazatetratetracontanoic acid
[CAS# 1118767-16-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: (S)-22-(tert-Butoxycarbonyl)-43,43-dimethyl-10,19,24,41-tetraoxo-3,6,12,15,42-pentaoxa-9,18,23-triazatetratetracontanoic acid
• Molecular Formula: C₄₃H₇₉N₃O₁₃
• Molecular Weight: 846.10
• CAS Registry Number: 1118767-16-0
• SMILES: CC(C)(C)OC(=O)CCCCCCCCCCCCCCCCC(=O)N[C@@H](CCC(=O)NCCOCCOCC(=O)NCCOCCOCC(=O)O)C(=O)OC(C)(C)C

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.484, Calc.^*
• Boiling Point: 940.6±65.0 ºC (760 mmHg), Calc.^*
• Flash Point: 522.7±34.3 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovory and Applicatios

(S)-22-(tert-Butyloxycarbonyl)-43,43-dimethyl-10,19,24,41-tetraoxo-3,6,12,15,42-pentaoxa-9,18,23-triazatetradecanoic acid is a complex organic compound and an important molecule in synthetic chemistry, especially in peptide synthesis. This compound, abbreviated as Boc-Lys-PEG-COOH, was developed to meet the growing demand for versatile intermediates in the synthesis of peptides and other complex molecules. Its discovery involves the coupling of lysine with polyethylene glycol (PEG) followed by the introduction of a tert-butoxycarbonyl (Boc) protecting group. Boc-Lys-PEG-COOH has a multifaceted structure: the tert-butoxycarbonyl (Boc) group acts as a protecting group for the amino functional group of lysine to prevent unwanted side reactions during peptide synthesis. The polyethylene glycol (PEG) segment gives it solubility in water and organic solvents, facilitating its use in a variety of reaction environments. The terminal carboxylic acid group provides a site for further functionalization or coupling reactions, making it a versatile intermediate.

Boc-Lys-PEG-COOH is widely used as a building block for peptide synthesis. Its protected lysine residue allows the sequential addition of amino acids without side reactions to form peptides. The Boc group can be removed under mild acidic conditions, exposing the amino group for further coupling steps. This process is essential for the synthesis of bioactive peptides and proteins for pharmaceutical and biochemical research.

The PEG chain in Boc-Lys-PEG-COOH allows for PEGylation, the process by which polyethylene glycol chains are attached to a peptide or protein. PEGylation enhances the solubility, stability, and bioavailability of therapeutic proteins, prolongs their half-life, and reduces immunogenicity. Boc-Lys-PEG-COOH provides a functionalized PEG moiety that can be easily introduced into bioactive molecules.

The compound is used as a linker when conjugating peptides to other molecules or surfaces. The carboxylic acid group can be activated to form esters or amides, allowing the peptide to be attached to drugs, nanoparticles, or solid supports. This linker functionality is critical for the development of targeted drug delivery systems, diagnostic assays, and bioconjugates.

In drug delivery, Boc-Lys-PEG-COOH is used to create PEGylated drug conjugates to improve the pharmacokinetics and biodistribution of therapeutic agents. PEGylated drugs exhibit prolonged circulation time and reduced clearance, thereby enhancing their efficacy and reducing side effects.

The compound is used in the development of diagnostic assays where the peptide is conjugated to a detection molecule or surface. The PEG chain helps maintain the solubility and accessibility of the peptide, thereby increasing the sensitivity and specificity of the assay.

Boc-Lys-PEG-COOH is used for surface modification to create biocompatible coatings. The PEG segment reduces protein adsorption and cell adhesion, making it suitable for medical devices and implants where biofouling needs to be minimized.

In the pharmaceutical industry, Boc-Lys-PEG-COOH is used to synthesize peptide-based drugs and conjugates. Its role in peptide synthesis and PEGylation supports the development of new therapeutics with improved properties.

In biotechnology, the compound facilitates the synthesis of bioactive peptides and proteins for research and diagnostic applications. Its versatility in conjugation and functionalization makes it a valuable tool for the development of advanced biotechnology products.

In academic research, Boc-Lys-PEG-COOH is used to explore new approaches to peptide synthesis, bioconjugation, and drug delivery.