4-(Azidomethyl)-L-phenylalanine hydrochloride
[CAS# 2517638-29-6]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Phenylalanine derivatives
• Name: 4-(Azidomethyl)-L-phenylalanine hydrochloride
• Synonyms: (S)-2-amino-3-(4-(azidomethyl)phenyl)propanoic acid hydrochloride
• Molecular Formula: C₁₀H₁₃ClN₄O₂
• Molecular Weight: 256.69
• CAS Registry Number: 2517638-29-6
• SMILES: N[C@@H](CC1=CC=C(CN=[N+]=[N-])C=C1)C(O)=O.[H]

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305+351+338-P302+352

Discovory and Applicatios

4-(Azidomethyl)-L-phenylalanine hydrochloride is a chemical compound that belongs to the class of modified amino acids. It is a derivative of the amino acid phenylalanine, where the hydrogen atom on the aromatic ring is replaced by an azidomethyl group (-CH2N3) at the 4-position. The hydrochloride salt form of this compound enhances its solubility in aqueous solutions, making it suitable for various biochemical and synthetic applications. The incorporation of the azide group into the phenylalanine structure introduces a highly reactive functionality that has proven valuable in chemical and biological research.

The discovery of 4-(Azidomethyl)-L-phenylalanine hydrochloride is part of ongoing efforts to develop amino acid derivatives with enhanced reactivity for use in peptide and protein synthesis. The azide group, known for its high reactivity in "click chemistry" reactions, allows for the selective conjugation of the amino acid derivative to other molecules. This reactivity is crucial for the design of bioconjugates, drug delivery systems, and molecular probes, making 4-(Azidomethyl)-L-phenylalanine hydrochloride a valuable tool in the fields of medicinal chemistry, molecular biology, and materials science.

One of the key applications of 4-(Azidomethyl)-L-phenylalanine hydrochloride is in the field of bioconjugation. The azide group on the side chain can participate in copper-catalyzed azide-alkyne cycloaddition (CuAAC), also known as "click chemistry." This reaction enables the efficient and selective attachment of the azide group to other chemical entities, such as fluorescent dyes, peptides, or drug molecules, without the need for complex protection and deprotection steps. The result is the formation of stable, highly functionalized conjugates that can be used for a wide range of applications, including the development of targeted therapeutics, diagnostic agents, and biomolecular sensors.

In peptide and protein chemistry, 4-(Azidomethyl)-L-phenylalanine hydrochloride serves as a building block for the synthesis of modified peptides and proteins. By incorporating this azidomethylated phenylalanine derivative into peptides, researchers can introduce azide functionality at specific locations within the peptide sequence. This modification allows for the subsequent conjugation of the peptide to various biomolecules, enabling the study of protein-protein interactions, the design of novel protein therapeutics, and the development of protein-based drug delivery systems.

Additionally, 4-(Azidomethyl)-L-phenylalanine hydrochloride is valuable in the creation of molecular probes. The azide group can be conjugated with fluorescent markers or other detection molecules, allowing researchers to track the location and movement of specific peptides or proteins within living cells. These probes are used in cell biology, molecular imaging, and drug screening to study the mechanisms of disease and the effects of potential therapeutic agents.

The compound also has potential applications in the synthesis of advanced materials. The azide group is a versatile functional group that can undergo various chemical reactions, including those that lead to the formation of cross-linked polymer networks. This makes 4-(Azidomethyl)-L-phenylalanine hydrochloride a useful monomer in the development of novel materials with tailored properties for applications in biotechnology, tissue engineering, and nanotechnology.

Overall, 4-(Azidomethyl)-L-phenylalanine hydrochloride is an important chemical reagent with a wide range of applications in chemical and biological research. Its azide functionality enables selective and efficient conjugation to other molecules, making it a valuable tool in drug discovery, peptide and protein synthesis, bioconjugation, and the development of advanced materials.