Thiol-PEG8-propionic acid

 CAS No.: 866889-02-3  Cat No.: BP-500596  Purity: >95% 4.5  

Thiol-PEG8-propionic acid is a PEG-based linker bearing a terminal thiol and a propionic acid group, providing a flexible, hydrophilic chain length of eight ethylene glycol units that can be used to spatially separate functional domains in conjugates. The thiol end enables chemoselective coupling strategies commonly used in PROTAC and targeted degradation workflows, including maleimide–thiol addition or thiol-reactive handle installation on ligands or scaffold components, while the carboxylic acid facilitates amide or ester formation for stable attachment to protein-binding moieties or degraders. In PROTAC design, this bifunctional linker serves as a controllable “molecular spacer” that tunes effective proximity and orientation between the target-binding ligand and the recruitment element, often improving conjugation efficiency and modulating ternary complex formation. Its PEG character also helps reduce nonspecific hydrophobic interactions and can enhance solubility of multi-component degradation constructs, supporting systematic linker optimization in targeted protein degradation research.

Thiol-PEG8-propionic acid

Structure of 866889-02-3

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Category
PROTAC Linker
Molecular Formula
C₁₉H₃₈O₁₀S
Molecular Weight
458.56
Appearance
Colorless Liquid

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

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Purity
>95%
Appearance
Colorless Liquid
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
3-[2-[2-[2-[2-[2-[2-[2-(2-sulfanylethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
Synonyms
HS-PEG8-CH2CH2COOH; 1-mercapto-3,6,9,12,15,18,21,24-Octaoxaheptacosan-27-oic acid
Boiling Point
559.7±50.0 °C at 760 mmHg
Density
1.1±0.1 g/cm3
InChI Key
SKYJRDAORYSCAL-UHFFFAOYSA-N
InChI
InChI=1S/C19H38O10S/c20-19(21)1-2-22-3-4-23-5-6-24-7-8-25-9-10-26-11-12-27-13-14-28-15-16-29-17-18-30/h30H,1-18H2,(H,20,21)
SMILES
C(COCCOCCOCCOCCOCCOCCOCCOCCS)C(=O)O

Thiol-PEG8-propionic acid is a polyethylene glycol-based PROTAC linker building block designed to provide a hydrophilic, flexible spacer between targeting and recruiting ligands. Its ether-rich backbone supports solubility and conformational adaptability, which can improve productive ternary complex formation. The terminal carboxylic acid enables straightforward conjugation to amine-containing ligands, while the thiol functionality supports controlled coupling strategies. Detailed structural and synthetic considerations are provided below.

Structure: The linker comprises an oligo(ethylene glycol) chain terminated by a thiol and a propionic acid moiety. It contains multiple ether linkages along the PEG backbone, with a carboxylic acid group and a reactive sulfhydryl handle. These features confer high polarity and flexible, solvated conformations.

Reactivity: The carboxylic acid can be activated for amide-bond formation using standard coupling chemistries, enabling attachment to primary or secondary amines under mild base and dehydrating conditions. The thiol can participate in thiol–maleimide or thiol–activated electrophile conjugations, typically requiring controlled pH to preserve nucleophilicity and minimize oxidation. In practice, inert atmosphere and thiol-stabilizing conditions are often used to maintain reactivity during PROTAC assembly.

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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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