Propargyl-PEG3-phosphonic acid

 CAS No.: 1714139-62-4  Cat No.: BP-501172  Purity: 98% 4.5  

Propargyl-PEG3-phosphonic acid is a PEG-based linker bearing a terminal propargyl group and a phosphonic acid functionality, providing a chemically versatile scaffold for PROTAC and targeted protein degradation workflows. Structurally, it comprises a short, three–ethylene glycol unit chain that confers aqueous solubility and spatial flexibility, while the propargyl handle enables copper-catalyzed azide–alkyne cycloaddition or related click-type conjugation strategies to connect the linker to one PROTAC module. The phosphonic acid group offers a strong, anionic interaction motif that can be used to tune local charge distribution and, in appropriate designs, to support conjugation or coordination-based attachment to complementary moieties. In PROTAC construction, this combination of a reactive alkynyl terminus and a phosphonic acid anchor helps researchers rationally position binding elements to promote effective ternary complex formation. As a linker reagent, it is valuable for generating degraders with improved solubility and controllable linker geometry, facilitating systematic structure–activity relationship studies in targeted degradation research.

Propargyl-PEG3-phosphonic acid

Structure of 1714139-62-4

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Category
PROTAC Linker
Molecular Formula
C₉H₁₇O₆P
Molecular Weight
252.20

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

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Purity
98%
Solubility
DMSO, DCM
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethylphosphonic acid
Synonyms
(2-(2-(2-(prop-2-yn-1-yloxy)ethoxy)ethoxy)ethyl)phosphonic acid; Propargyl-PEG3-phosphonicacid; 2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethylphosphonic acid
InChI Key
OUKZOEDGARPKKQ-UHFFFAOYSA-N
InChI
InChI=1S/C9H17O6P/c1-2-3-13-4-5-14-6-7-15-8-9-16(10,11)12/h1H,3-9H2,(H2,10,11,12)
SMILES
C#CCOCCOCCOCCP(=O)(O)O

Propargyl-PEG3-phosphonic acid is a versatile PROTAC linker building block designed to connect targeting ligands through a PEG-based spacer while incorporating a phosphonic acid handle for robust conjugation strategies. Its flexible, hydrophilic architecture can help tune linker solvation and presentation to improve ternary complex formation. The propargyl functionality enables reliable click-type coupling, and the phosphonic acid provides an additional orthogonal reactive motif. Detailed structural and synthetic considerations are provided below.

Structure: This linker combines a terminal propargyl group with a short polyethylene glycol chain and a phosphonic acid moiety. It contains carbon–carbon and carbon–oxygen bonds within the PEG segment, along as a carbon–carbon triple bond suitable for bioorthogonal coupling, and a phosphorus–oxygen framework that confers strong acidity and metal-binding character.

Reactivity: The propargyl group is well suited for copper-catalyzed azide–alkyne cycloaddition or related alkyne-based conjugation approaches, typically requiring an appropriate azide partner, a compatible copper catalyst system, and oxygen-tolerant conditions to preserve sensitive ligands. The phosphonic acid can participate in coupling workflows that rely on activation of the P–OH group or coordination-assisted assembly, often using polar, buffering-compatible solvents to maintain solubility and functional-group stability during PROTAC construction.

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It is commonly abbreviated as: C1V1 = C2V2

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