N-(NHS-PEG3)-N-bis(PEG3-azide)
CAS No.: 2182602-16-8
Cat No.: BP-501218
Purity: 98%
4.5 
N-(NHS-PEG3)-N-bis(PEG3-azide) is a heterobifunctional PEG-based linker designed for covalent attachment to amine-containing targeting ligands via an N-hydroxysuccinimide (NHS) ester, followed by azide-mediated conjugation. Structurally, it comprises an NHS-activated PEG3 segment coupled to a tertiary nitrogen that connects to two PEG3 arms terminated with azide groups, providing a short, flexible hydrophilic spacer while maintaining two orthogonal reactive handles. In PROTAC construction, the NHS ester enables rapid formation of stable amide bonds with primary amines on one component (e.g., a ligand or binding moiety), while the terminal azides allow subsequent chemoselective ligation, most commonly through copper-free click chemistry with alkyne-functional partners. This dual-reactivity supports modular assembly of degraders, improves effective molarity and solubility, and facilitates controlled stoichiometry when linking to E3 ligase recruiters or other functional modules, thereby streamlining synthesis and enabling systematic structure–activity studies.
Structure of 2182602-16-8
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This PROTAC linker, N-(NHS-PEG3)-N-bis(PEG3-azide), is designed to connect a protein-binding handle to a second functional moiety through a flexible polyethylene glycol scaffold. Its NHS ester enables efficient conjugation to primary amines under mild conditions, while the azide groups provide orthogonal “click” reactivity for subsequent assembly steps. These features make it well suited for modular PROTAC construction, where controlled linker geometry and reliable chemoselectivity are essential. Detailed structural and reactivity considerations are provided below.
Structure: The molecule contains an activated N-hydroxysuccinimide ester attached to a PEG-based chain, along with multiple terminal azide functionalities. It is characterized by ether-rich PEG segments, an amide-linked NHS unit, and azide groups suitable for bioorthogonal cycloaddition chemistry, yielding a hydrophilic, flexible linker.
Reactivity: The NHS ester reacts with primary amines via nucleophilic acyl substitution, typically in buffered aqueous or mixed solvent systems at conditions that preserve protein integrity. The resulting amide linkage can then be coupled using copper-catalyzed or copper-free azide–alkyne cycloaddition, depending on protein sensitivity and desired compatibility. Solvent choice and reagent stoichiometry should be optimized to balance conjugation efficiency and minimize side reactions such as hydrolysis of the NHS ester.
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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