N-(Azido-PEG3)-N-bis(PEG3-acid)

 CAS No.: 2055042-57-2  Cat No.: BP-501058  Purity: 97% 4.5  

N-(Azido-PEG3)-N-bis(PEG3-acid) is a heterobifunctional polyethylene glycol (PEG)-based PROTAC linker featuring an azide handle for bioorthogonal conjugation and two terminal PEG3 carboxylic acid groups for controlled attachment to complementary PROTAC modules. Structurally, it comprises a central tertiary amine bearing an azide-terminated PEG3 segment and two PEG3-acid arms, yielding a flexible, hydrophilic, and water-compatible linkage architecture with multiple functional termini. In PROTAC design, the azide enables efficient coupling to alkyne-bearing warheads or E3-ligase ligands via CuAAC with a terminal alkyne or SPAAC with a strained cyclooctyne, while the carboxylic acids provide sites for amide bond formation or salt formation to tune solubility, linker length, and spatial orientation between binding domains. This linker is valuable for constructing modular degraders, facilitating rapid synthesis of analog libraries, and improving aqueous handling and conjugation efficiency during targeted protein degradation research.

N-(Azido-PEG3)-N-bis(PEG3-acid)

Structure of 2055042-57-2

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Category
PROTAC Linker
Molecular Formula
C₂₆H₅₀N₄O₁₃
Molecular Weight
626.69

* For research and manufacturing use only. Not for human or clinical use.

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Purity
97%
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
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Room temperature in continental US; may vary elsewhere.
IUPACName
3-[2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl-[2-[2-[2-(2-carboxyethoxy)ethoxy]ethoxy]ethyl]amino]ethoxy]ethoxy]ethoxy]propanoic acid
Synonyms
N-(Azido-PEG3)-N-bis(PEG3-acid) HCl salt
InChI Key
ZFRXULKENCQWKC-UHFFFAOYSA-N
InChI
InChI=1S/C26H50N4O13/c27-29-28-3-9-37-15-21-43-24-18-40-12-6-30(4-10-38-16-22-41-19-13-35-7-1-25(31)32)5-11-39-17-23-42-20-14-36-8-2-26(33)34/h1-24H2,(H,31,32)(H,33,34)
SMILES
C(COCCOCCOCCN(CCOCCOCCOCCC(=O)O)CCOCCOCCOCCN=[N+]=[N-])C(=O)O

This N-(Azido-PEG3)-N-bis(PEG3-acid) linker is designed for modular construction of PROTACs, providing a flexible polyethylene glycol-based spacer that can improve solubility and enable efficient conjugation to targeting ligands. The azide handle supports bioorthogonal click chemistry, while the terminal carboxylate groups offer reliable points for amide coupling or other linker-ligand attachment strategies. Detailed structural and reactivity considerations are provided below.

Structure: The linker contains an azide functional group attached to a short PEG segment, along with bis(PEG3-acid) termini bearing carboxylic acid functionalities. It is characterized by ether-rich PEG chains, flexible C–O linkages, and an azide moiety suitable for click reactions, contributing to favorable hydrophilicity and conformational mobility.

Reactivity: The azide group is suitable for copper-catalyzed azide–alkyne cycloaddition or strain-promoted azide–alkyne cycloaddition, enabling selective formation of triazole-linked PROTAC architectures. Carboxylic acids at the PEG termini can be activated for amide bond formation using standard coupling chemistries, typically under inert or controlled conditions in polar organic solvents. Reaction design should consider PEG compatibility, aqueous solubility, and preservation of sensitive targeting-ligand functionalities.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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