Name: Fmoc-DAP-N3
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

1-(Fmoc-amino)-3-azidopropylene; 1-(Fmoc-amino)-3-azidopropane; 9H-Fluoren-9-ylmethyl N-(3-azidopropyl)carbamate

IUPAC Name

9H-fluoren-9-ylmethyl N-(3-azidopropyl)carbamate

Canonical SMILES

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

InChI

InChI=1S/C18H18N4O2/c19-22-21-11-5-10-20-18(23)24-12-17-15-8-3-1-6-13(15)14-7-2-4-9-16(14)17/h1-4,6-9,17H,5,10-12H2,(H,20,23)

InChIKey

XXWDONRFYHZMAK-UHFFFAOYSA-N

Melting Point

80-88°C

Appearance

Whitw crytalline powder

Storage

Store at 2-8 °C

Fmoc-DAP-N3 is a protected derivative of diaminopropionic acid, commonly used in peptide synthesis and bioconjugation applications. Here are some key applications of Fmoc-DAP-N3:

Peptide Synthesis: Fmoc-DAP-N3 is employed in solid-phase peptide synthesis (SPPS) for creating complex peptides with functional groups. The azide group on Fmoc-DAP-N3 can be used for subsequent click chemistry reactions, enabling the attachment of various molecules to the peptide. This facilitates the production of peptides with tailored functionalities for research and therapeutic purposes.

Bioconjugation: In bioconjugation, Fmoc-DAP-N3 allows for the convenient attachment of peptides to other biomolecules such as proteins or nucleic acids through click chemistry. The azide group reacts with alkynes in a copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction, forming a stable triazole linkage. This method is widely used in the development of biomolecule conjugates for drug delivery, imaging, and diagnostic applications.

Drug Development: Fmoc-DAP-N3 can be used in the development of drug candidates by linking active pharmaceutical ingredients (APIs) to targeting peptides. The azide functionality enables easy and efficient conjugation with various drug molecules, enhancing their delivery and specificity. This approach can improve the therapeutic index of drugs and reduce off-target effects.

Protein Engineering: In protein engineering, Fmoc-DAP-N3 can be incorporated into protein sequences to introduce reactive azide groups. This allows site-specific modification of proteins through click chemistry, facilitating the study of protein interactions and functions. Such modifications can be used to enhance protein stability, activity, or for the creation of novel protein-based materials.