[2-[2-(Fmoc-amino)ethoxy]ethoxy]acetic acid
[CAS# 166108-71-0]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> FMOC-amino acid
• Name: [2-[2-(Fmoc-amino)ethoxy]ethoxy]acetic acid
• Synonyms: 8-(Fmoc-amino)-3,6-dioxaoctanoic acid; [2-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)ethoxy]ethoxy]acetic acid
• Molecular Formula: C₂₁H₂₃NO₆
• Molecular Weight: 385.41
• CAS Registry Number: 166108-71-0
• EC Number: 805-205-6
• SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NCCOCCOCC(=O)O

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.580, Calc.^*
• Boiling Point: 631.4±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 335.6±28.7 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

[2-[2-(Fmoc-amino)ethoxy]ethoxy]acetic acid, commonly referred to as Fmoc-EEA, is a chemical compound belonging to the class of amino acids modified with a fluorenylmethoxycarbonyl (Fmoc) protecting group. The discovery of this compound is part of the broader field of peptide synthesis, where Fmoc-based strategies have gained prominence for their effectiveness in protecting amino groups during the stepwise assembly of peptides. The development of Fmoc-EEA can be traced back to the advancements in organic synthesis and the need for efficient methods to construct complex peptide structures.

The Fmoc group serves as a protective moiety that allows for the selective deprotection of amino acids during peptide synthesis, making it a valuable tool in organic and medicinal chemistry. The incorporation of ethoxy chains enhances the solubility and stability of the compound, facilitating its application in various biological and chemical contexts. Fmoc-EEA is primarily used as a building block in the synthesis of peptides and other bioactive molecules, enabling researchers to create compounds with specific functionalities and biological activities.

One of the key applications of Fmoc-EEA is in the field of drug discovery, where it is utilized to construct peptides that can serve as potential therapeutic agents. The ability to modify peptides with various functional groups allows for the exploration of structure-activity relationships, helping researchers to identify and optimize candidates for drug development. Additionally, Fmoc-EEA can be employed in the preparation of peptide-based biomaterials, where its unique properties contribute to the development of scaffolds for tissue engineering and regenerative medicine.

In addition to its role in peptide synthesis, Fmoc-EEA has applications in the development of biosensors and diagnostic tools. Its amino and carboxylic acid functional groups can be utilized to create conjugates with biomolecules, enabling the detection of specific targets in biological samples. The versatility of Fmoc-EEA makes it a valuable component in the design of assays and sensors for applications in clinical diagnostics and environmental monitoring.

Moreover, the ease of synthesis and modification of Fmoc-EEA allows researchers to tailor its properties for specific applications, contributing to advancements in areas such as drug delivery and molecular imaging. The integration of Fmoc-EEA into larger peptide or protein constructs can enhance stability, solubility, and bioavailability, which are crucial factors in the efficacy of therapeutic agents.

Safety considerations associated with Fmoc-EEA indicate that, like many chemical substances used in laboratory settings, proper handling and safety protocols should be observed. While Fmoc-EEA is not classified as hazardous, it is essential to use appropriate personal protective equipment (PPE) and adhere to established guidelines when working with chemical compounds in the laboratory.

In summary, [2-[2-(Fmoc-amino)ethoxy]ethoxy]acetic acid is a versatile and valuable compound in the field of peptide synthesis and drug discovery. Its unique structural features and protective properties make it an essential building block for creating bioactive peptides and biomaterials, while its applications extend to the development of diagnostic tools and drug delivery systems.

References

2024. Macrocyclizing-thioesterases in bacterial non-ribosomal peptide biosynthesis. Journal of Natural Medicines.
DOI: 10.1007/s11418-024-01841-y

2020. A novel peptide-based electrochemical biosensor for the determination of a metastasis-linked protease in pancreatic cancer cells. Analytical and Bioanalytical Chemistry.
DOI: 10.1007/s00216-020-02418-w

2019. Synthesis and characterization of NH2-(AEEA)n-amphotericin B derivatives. The Journal of Antibiotics.
DOI: 10.1038/s41429-018-0138-8