Name: Fmoc-N-(4-azidobutyl)glycine
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

Fmoc-Abg(N3)-OH; 2-[4-Azidobutyl(9H-fluoren-9-ylmethoxycarbonyl)amino]acetic acid

IUPAC Name

2-[4-azidobutyl(9H-fluoren-9-ylmethoxycarbonyl)amino]acetic acid

Canonical SMILES

C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N(CCCCN=[N+]=[N-])CC(=O)O

InChI

InChI=1S/C21H22N4O4/c22-24-23-11-5-6-12-25(13-20(26)27)21(28)29-14-19-17-9-3-1-7-15(17)16-8-2-4-10-18(16)19/h1-4,7-10,19H,5-6,11-14H2,(H,26,27)

InChIKey

BCWAOXCPEFZRDL-UHFFFAOYSA-N

Melting Point

101-102°C

Appearance

White crystalline powder

Storage

Store at 2-8 °C

Fmoc-N-(4-azidobutyl)glycine, a modified amino acid with unique applications in biochemical research, offers diverse possibilities in various scientific endeavors. Here are four key applications of this compound:

Peptide Synthesis: Utilizing Fmoc-N-(4-azidobutyl)glycine in peptide synthesis allows for the creation of peptides with precise modifications. The introduction of the azide group into peptides sets the stage for subsequent click chemistry reactions. This innovative approach enables the attachment of a myriad of functional groups, facilitating the detailed study of protein interactions and the development of cell-penetrating peptides.

Photoaffinity Labeling: The presence of the azide moiety in Fmoc-N-(4-azidobutyl)glycine is advantageous for conducting photoaffinity labeling experiments. Upon exposure to UV irradiation, the azide group generates a reactive nitrene that can form covalent bonds with neighboring biomolecules. This methodology proves invaluable in the identification and exploration of protein-protein interactions within intricate biological systems, shedding light on molecular complexities.

Bioconjugation: A fundamental component of bioconjugation strategies, Fmoc-N-(4-azidobutyl)glycine is pivotal for conjugating biomolecules such as proteins and nucleic acids. The azide functionality of this compound facilitates click chemistry, enabling the attachment of fluorescent dyes, biotin, or other tags. Such modifications play a crucial role in the visualization, tracking, and purification of biomolecules, amplifying the scope of biotechnological applications.

Protein Engineering: Incorporating Fmoc-N-(4-azidobutyl)glycine into proteins offers a realm of possibilities for creating site-specific modifications. This innovative approach aids in engineering proteins with novel functions or enhanced stability. These modified proteins find utility in diverse fields such as drug development, enzyme catalysis, and structural biology studies, showcasing the versatility and potential of this compound in advancing biotechnological frontiers.