17-Amino-10-oxo-3,6,12,15-tetraoxa-9-azaheptadecanoic acid
[CAS# 1143516-05-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty acid
• Name: 17-Amino-10-oxo-3,6,12,15-tetraoxa-9-azaheptadecanoic acid
• Synonyms: 2-[2-[2-[[2-[2-(2-aminoethoxy)ethoxy]acetyl]amino]ethoxy]ethoxy]acetic acid
• Molecular Formula: C₁₂H₂₄N₂O₇
• Molecular Weight: 308.33
• CAS Registry Number: 1143516-05-5
• EC Number: 815-071-0
• SMILES: C(COCCOCC(=O)NCCOCCOCC(=O)O)N

Properties

• Solubility: Freely soluble (999 g/L) (25 °C), Calc.^*
• Density: 1.202±0.06 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

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

17-Amino-10-oxo-3,6,12,15-tetraoxa-9-azaheptadecanoic acid is a synthetic chemical compound commonly used in biochemistry and medicinal chemistry. This molecule is characterized by its amide bond and multiple ether linkages, which make it useful for various applications, particularly in the modification of peptides and proteins. The presence of the amino group provides a reactive site for coupling reactions, making this compound an important tool in the design of biologically active molecules.

The discovery of compounds like 17-amino-10-oxo-3,6,12,15-tetraoxa-9-azaheptadecanoic acid can be traced to efforts in peptide chemistry to develop linkers and spacers that can modify peptides without interfering with their biological activity. This compound serves as a flexible linker due to its tetraoxa-structure, which allows for spatial separation between functional groups while maintaining structural integrity. These properties are useful in drug design, where the controlled flexibility of molecular linkers can influence the bioactivity, solubility, and stability of drug candidates.

In terms of application, 17-amino-10-oxo-3,6,12,15-tetraoxa-9-azaheptadecanoic acid is primarily used as a building block in peptide synthesis. It facilitates the attachment of biologically relevant molecules, such as fluorescent dyes or therapeutic agents, to peptides or proteins. The ether linkages in its structure help maintain a balance between hydrophilicity and lipophilicity, which is crucial for the solubility and overall pharmacokinetic properties of the modified biomolecules.

This compound is also used in the development of polymer-drug conjugates, where it acts as a linker that can join therapeutic molecules to polymers, thereby enhancing drug delivery systems. These conjugates often improve the solubility and stability of drugs, allowing for controlled release and improved efficacy in targeted treatments. The ability to control the length and flexibility of the linker makes 17-amino-10-oxo-3,6,12,15-tetraoxa-9-azaheptadecanoic acid a valuable tool in these advanced therapeutic technologies.

Additionally, this compound plays a role in the preparation of bioconjugates for diagnostic purposes. By attaching this molecule to peptides or proteins, researchers can develop probes that are used in imaging techniques to track the behavior of biological systems in real-time. This has proven useful in medical diagnostics and in the study of disease mechanisms.

References

2021. Structure and dynamics of semaglutide- and taspoglutide-bound GLP-1R-Gs complexes. Cell Reports.
DOI: 10.1016/j.celrep.2021.109374

2007. RGD targeted poly(L-glutamic acid)-cystamine-(Gd-DO3A) conjugate for detecting angiogenesis biomarker alpha(v) beta3 integrin with MRT, mapping. International journal of nanomedicine.
URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2673968