35-Azido-3,6,9,12,15,18,21,24,27,30,33-undecaoxapentatriacontan-1-amine
Molecular Formula: C24H50N4O11
CAS#: 1800414-71-4
SMILES: NCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCN=[N+]=[N-]
MDL#: MFCD08274605
Catalog#: AMTGC1166-AU23
Molecular weight: 570.67 g/mol
Appearance: Colorless liquid
Purity: 95.1%
Storage: Long-term storage in a freezer at -20°C
Solubility: Dichloromethane, Chloroform, Methanol
Other names:
- Azido-PEG11-amine
- N3-PEG11-CH2CH2NH2
- Azido-PEG12-amine
Fields of Interest:
Click chemistry, Bioconjugation, Chemical biology, Drug delivery, PROTAC development, ADC research, Biomaterials, Polymer modification, Surface functionalization, Specialty chemical synthesis
Background
Azido-PEG11-amine (CAS 1800414-71-4) is a long-chain, heterobifunctional PEG linker containing a terminal azide (N₃) and a terminal primary amine (NH₂) separated by a hydrophilic PEG11 spacer. The extended polyethylene glycol chain provides substantial molecular spacing, flexibility, and hydrophilicity, making this linker particularly useful when greater separation between conjugated molecules is desired.
The two terminal groups provide complementary and orthogonal conjugation strategies. The azide enables copper-catalyzed azide–alkyne cycloaddition (CuAAC) and strain-promoted azide–alkyne cycloaddition (SPAAC), while the primary amine can be coupled with carboxylic acids, activated NHS esters, and other amine-reactive functionalities. This combination makes Azido-PEG11-amine a versatile building block within a comprehensive portfolio of functionalized PEGs for modular molecular assembly.
Applications
Azido-PEG11-amine is useful in bioconjugation, chemical biology, drug delivery, PROTAC development, biomaterials, and specialty chemical synthesis. Its long PEG11 spacer can provide controlled molecular separation while increasing the hydrophilic character of conjugates.
The terminal amine provides a convenient site for attachment to proteins, peptides, small molecules, polymers, surfaces, or other compounds containing compatible amine-reactive groups. The remaining azide can subsequently participate in click chemistry with alkyne-, DBCO-, or BCN-functionalized molecules. Alternatively, the reaction sequence can be reversed when compatible with the other components of the system. This orthogonality makes the compound particularly valuable for multistep conjugation strategies and construction of complex molecular architectures. Commercial sources also identify Azido-PEG11-amine as a PEG linker for PROTAC synthesis.
Literature:
- Chemistry – A European Journal, 2017, vol. 23, # 19, p. 4730 – 4735
- Organic Process Research and Development, 2024, vol. 28, # 10, p. 3913 – 3921
- Organic Letters, 2017, vol. 19, # 10, p. 2560 – 2563
