Name: (2R,3R)-(Fmoc-amino)-3-azidobutyric acid
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

Fmoc-D-Abu(3R-N3)-OH; (2R,3R)-3-Azido-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid

IUPAC Name

(2R,3R)-3-azido-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid

Canonical SMILES

CC(C(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)N=[N+]=[N-]

InChI

InChI=1S/C19H18N4O4/c1-11(22-23-20)17(18(24)25)21-19(26)27-10-16-14-8-4-2-6-12(14)13-7-3-5-9-15(13)16/h2-9,11,16-17H,10H2,1H3,(H,21,26)(H,24,25)/t11-,17-/m1/s1

InChIKey

LLJMYBCJYQGZOS-PIGZYNQJSA-N

Melting Point

147-154°C

Appearance

White crystalline powder

Storage

Store at 2-8 °C

(2R,3R)-(Fmoc-amino)-3-azidobutyric acid, a specialized chemical reagent, finds diverse applications in bioscience research, particularly in peptide and protein synthesis. Here are four key applications, presented with a high degree of perplexity and burstiness:

Peptide Synthesis: Integral to solid-phase peptide synthesis, (2R,3R)-(Fmoc-amino)-3-azidobutyric acid acts as a pivotal building block, introducing an azide functional group into the peptide chain. This functional group serves as a catalyst for click chemistry reactions, paving the way for the creation of peptides adorned with a myriad of modifications and conjugations. Such versatility enhances the utility of peptides in both research and therapeutic realms, offering a broad spectrum of potential applications.

Chemical Biology: Embraced in the realm of chemical biology, this compound facilitates the exploration of protein-protein interactions. The azide group within (2R,3R)-(Fmoc-amino)-3-azidobutyric acid opens doors to bioorthogonal labeling through click chemistry, enabling seamless attachment of diverse probes or tags to proteins of interest. This capability revolutionizes the visualization, tracking, and analysis of proteins within intricate biological systems, shedding light on the complexities of molecular interactions.

Drug Discovery: A cornerstone of drug discovery endeavors, (2R,3R)-(Fmoc-amino)-3-azidobutyric acid emerges as a key player in synthesizing modified peptides for potential drug candidates. The incorporation of an azide group provides a versatile platform for subsequent chemical modifications, including the addition of pharmacophores or targeting moieties. This strategic approach holds the promise of developing peptide-based therapeutics with enhanced pharmacokinetic and pharmacodynamic properties, reshaping the landscape of drug development.

Bioconjugation: Positioned at the forefront of bioconjugation strategies, the azide functionality of (2R,3R)-(Fmoc-amino)-3-azidobutyric acid underscores its indispensability in linking peptides or proteins to a spectrum of biomolecules like nucleic acids, lipids, or carbohydrates through click chemistry. This innovative technique paves the way for the creation of multifunctional bioconjugates with diverse applications in diagnostics, imaging, and targeted delivery systems, propelling forward the frontiers of bioengineering and biomedicine.