Name: Thalidomide-O-C3-acid
Brand: BOC Sciences
Rating: 5 (1 reviews)

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IUPACName

4-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]oxybutanoic acid

InChI Key

CQVOUORLTYFMHW-UHFFFAOYSA-N

InChI

1S/C17H16N2O7/c20-12-7-6-10(15(23)18-12)19-16(24)9-3-1-4-11(14(9)17(19)25)26-8-2-5-13(21)22/h1,3-4,10H,2,5-8H2,(H,21,22)(H,18,20,23)

Canonical SMILES

OC(CCCOC1=C2C(N(C(C2=CC=C1)=O)C3CCC(NC3=O)=O)=O)=O

Pub Chem ID

132212112

Background Introduction

Thalidomide-O-C3-acid is a specialized E3 ligase ligand-linker conjugate, designed for use in PROTAC (Proteolysis Targeting Chimera) technology. This molecule combines a thalidomide-based CRBN (Cereblon) ligand with a short, three-carbon linker terminating in a carboxylic acid group, making it ideal for further chemical conjugation. By serving as a modular building block, Thalidomide-O-C3-acid facilitates the development of next-generation targeted protein degraders.

Mechanism

The mechanism of Thalidomide-O-C3-acid centers on targeted protein degradation via the ubiquitin-proteasome system. The thalidomide moiety specifically binds to the CRBN E3 ubiquitin ligase, while the carboxylic acid terminus enables straightforward coupling to target protein ligands (warheads). When incorporated into a PROTAC, this conjugate mediates the close proximity of CRBN to the protein of interest, promoting ubiquitination and subsequent proteasomal degradation.

Applications

Thalidomide-O-C3-acid is extensively used in drug discovery, particularly in the synthesis of custom PROTAC molecules for targeted protein degradation studies. It is suitable for developing PROTACs aimed at CRBN-recruiting for various disease-related target proteins. Researchers utilize this conjugate to accelerate the production of novel protein degraders in oncology, neurodegeneration, and other therapeutic areas where selective protein knockdown is desirable. Its modular design and proven CRBN-binding efficiency make Thalidomide-O-C3-acid an essential tool in chemical biology and medicinal chemistry.

• Carboxyl-functionalized linker enables versatile coupling for PROTAC development
• Ideal for CRBN E3 ligase recruitment in next-generation targeted protein degradation

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* 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