17-Azido-3,6,9,12,15-pentaoxaheptadecan-1-amine
Molecular Formula: C12H26N4O5
CAS#: 516493-93-9
SMILES: NCCOCCOCCOCCOCCOCCN=[N+]=[N-]
MDL#: MFCD16619318
Catalog#: AMTGC281-AP17
Molecular weight: 306.36 g/mol
Appearance: Pale orange liquid
Purity: 97.7%
Storage: Long-term storage in a freezer at -20 °C
Solubility: Dichloromethane, Chloroform, Methanol
Other names:
- Azido-PEG5-amine
- N3-PEG5-NH2
- N3-PEG5-CH2CH2NH2
- O-(2-Aminoethyl)-O′-(2-azidoethyl)tetraethylene glycol
Fields of Interest:
Click chemistry, bioconjugation, chemical biology, drug delivery, PROTAC development, ADC research, biomaterials, polymer chemistry, surface functionalization, molecular linker synthesis, specialty chemical synthesis
Background
17-Azido-3,6,9,12,15-pentaoxaheptadecan-1-amine (CAS 516493-93-9) is a heterobifunctional PEG5 linker containing a terminal azide (N₃) and a terminal primary amine (NH₂). The flexible polyethylene glycol spacer provides hydrophilic character and molecular separation between the two reactive termini, making this compound useful for constructing conjugates where controlled spacing and complementary functional groups are desired.
The azide provides a bioorthogonal handle for copper-catalyzed azide–alkyne cycloaddition (CuAAC) and strain-promoted azide–alkyne cycloaddition (SPAAC), while the primary amine provides a site for conventional conjugation with carboxylic acids, activated esters such as NHS esters, isocyanates, and other amine-reactive functionalities. The combination of these orthogonal groups makes Azido-PEG5-amine a versatile building block within a comprehensive portfolio of functionalized PEGs for modular molecular assembly.
Applications
Azido-PEG5-amine is useful in bioconjugation, click chemistry, chemical biology, drug delivery research, PROTAC development, biomaterials, polymer modification, and specialty chemical synthesis. The primary amine can be used to attach the PEG spacer to proteins, peptides, small molecules, polymers, surfaces, or other appropriately activated substrates while preserving the terminal azide for subsequent click chemistry.
Conversely, the azide can first be reacted with an alkyne, DBCO, or BCN-functionalized component, leaving the primary amine available for a second conjugation step. This orthogonality makes the compound particularly useful for multistep conjugation strategies, linker construction, surface functionalization, and preparation of complex molecular architectures. Commercial sources also identify Azido-PEG5-amine as a PEG-based linker for PROTAC development.
Literature:
- WO2008/72976, 2008, A2
