2-(Azido-PEG3-amido)-1,3-bis(carboxylethoxy)propane

 CAS No.: 2086689-05-4  Cat No.: BP-500524  Purity: 98% 4.5  

2-(Azido-PEG3-amido)-1,3-bis(carboxylethoxy)propane is a heterobifunctional PEG-based linker featuring an azide handle and an amide-linked PEG3 segment connected to a substituted propane core bearing two carboxylethoxy termini. Structurally, the azide enables bioorthogonal conjugation chemistry, most commonly via copper-free azide–alkyne cycloaddition or related click reactions, allowing researchers to attach the linker to complementary PROTAC modules such as ligands bearing alkynes or other azide-reactive partners. The PEG3 spacer provides conformational flexibility and improved solubility, which can reduce steric constraints and help maintain productive geometry for ternary complex formation between a target-binding ligand and an E3 ligase recruiter. The dual carboxylate groups offer additional options for further derivatization, buffering of charge, and controlled attachment strategies during PROTAC synthesis. As a modular PEG linker, it is valuable for systematic optimization of linker length, polarity, and attachment points in targeted protein degradation studies.

2-(Azido-PEG3-amido)-1,3-bis(carboxylethoxy)propane

Structure of 2086689-05-4

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PROTAC Linker
Molecular Formula
C₁₈H₃₂N₄O₁₀
Molecular Weight
464.47

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

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Purity
98%
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-[3-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]propanoylamino]-3-(2-carboxyethoxy)propoxy]propanoic acid
Synonyms
2-Azido-PEG3-amido-13-biscarboxylethoxypropane; 3-[2-(3-{2-[2-(2-azidoethoxy)ethoxy]ethoxy}propanamido)-3-(2-carboxyethoxy)propoxy]propanoic acid; 3-[2-[3-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]propanoylamino]-3-(2-carboxyethoxy)propoxy]propanoic acid; Propanoic acid, 3-[[15-azido-2-[(2-carboxyethoxy)methyl]-4-oxo-7,10,13-trioxa-3-azapentadec-1-yl]oxy]-
InChI Key
NIEBYMXGDWQDQN-UHFFFAOYSA-N
InChI
InChI=1S/C18H32N4O10/c19-22-20-4-8-29-10-12-30-11-9-28-5-1-16(23)21-15(13-31-6-2-17(24)25)14-32-7-3-18(26)27/h15H,1-14H2,(H,21,23)(H,24,25)(H,26,27)
SMILES
C(COCCOCCOCCN=[N+]=[N-])C(=O)NC(COCCC(=O)O)COCCC(=O)O

2-(Azido-PEG3-amido)-1,3-bis(carboxylethoxy)propane, provides a PEG-based spacer incorporating an azide handle and amide functionality, enabling modular assembly of targeted protein degraders. Its bifunctional carboxylate groups support robust conjugation strategies, while the azide enables efficient bioorthogonal coupling. These features make it well-suited for constructing PROTACs with controlled linker length, polarity, and attachment geometry; detailed structural and synthetic guidance is provided below.

Structure: The linker contains a poly(ethylene glycol) segment, an azide-bearing substituent, and an amide linkage, along with two carboxylate-terminated ethoxy substituents. It features ether and amide bonds that confer flexibility and hydrogen-bonding capacity, and a terminal azide suitable for click-type transformations.

Reactivity: The azide group is typically used in copper-catalyzed azide–alkyne cycloaddition or related azide-based conjugation approaches, enabling attachment to alkyne-functional warheads under standard click conditions. The carboxylate groups are commonly activated (for example, via carbodiimide coupling) to form amide bonds with amine-bearing ligands. Mild aqueous or mixed organic solvent systems and appropriate coupling bases are generally employed to preserve sensitive functional groups.

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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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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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