Name: Fmoc-N-(2-azidoethyl)glycine
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

Fmoc-Aeg(N3)-OH; 2-[2-Azidoethyl(9H-fluoren-9-ylmethoxycarbonyl)amino]acetic acid

IUPAC Name

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

Canonical SMILES

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

InChI

InChI=1S/C19H18N4O4/c20-22-21-9-10-23(11-18(24)25)19(26)27-12-17-15-7-3-1-5-13(15)14-6-2-4-8-16(14)17/h1-8,17H,9-12H2,(H,24,25)

InChIKey

MLMPWBUAQAXGFT-UHFFFAOYSA-N

Melting Point

109-111°C

Appearance

White crystalline powder

Storage

Store at 2-8 °C

Fmoc-N-(2-azidoethyl)glycine, a specialized reagent crucial for peptide synthesis and bioconjugation applications. Here are four key applications of Fmoc-N-(2-azidoethyl)glycine:

Peptide Synthesis: Playing a pivotal role in solid-phase peptide synthesis (SPPS), Fmoc-N-(2-azidoethyl)glycine serves as a fundamental building block. Its azido group enables the implementation of orthogonal protection strategies, elevating the efficiency of peptide chain assembly while minimizing undesirable side reactions. This capability allows for the streamlined synthesis of intricate functional peptides utilized in both research and therapeutic contexts.

Bioconjugation: Acting as a catalyst for peptide attachment to diverse biomolecules via click chemistry, this compound offers a targeted approach. The azido group exhibits a highly specific and efficient reactivity with alkyne-functionalized molecules, fostering the formation of stable triazole linkages. This application is indispensable for crafting peptide conjugates essential in cutting-edge drug delivery systems and diagnostic assays, enhancing precision and efficacy.

Chemical Biology: In the realm of chemical biology, Fmoc-N-(2-azidoethyl)glycine emerges as a valuable tool for investigating protein-protein interactions and protein labeling. Through the integration of this azide-functionalized glycine into peptides or proteins, researchers can leverage bioorthogonal chemistry to tag these molecules with fluorescent probes or affinity labels.

Material Science: Within the domains of nanotechnology and materials science, Fmoc-N-(2-azidoethyl)glycine finds utility in surface functionalization and nanoparticle applications. The azide group’s participation in click chemistry reactions allows for the immobilization of peptides and other biomolecules on diverse substrates, facilitating the design of bioactive surfaces, biosensors, and targeted delivery systems.