Name: Pomalidomide-C4-COOH
Brand: BOC Sciences
Rating: 5 (1 reviews)

Size

Price

Stock

Quantity

$--

In stock

Purity

≥95%

Solubility

Soluble in DMF, DMSO

Appearance

Yellow Solid

Storage

Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)

IUPACName

5-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]pentanoic acid

Synonyms

Pomalidomide-C4-acid; Pentanoic acid, 5-[[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]amino]-; 5-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)pentanoic acid; 5-[[2-(2,6-Dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]amino]pentanoic acid; 5-{[2-(2,6-Dioxo-3-piperidinyl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]amino}pentanoic acid; Pomalidomide 4'-alkylC4-acid; JUN 40485; JUN-40485; Thalidomide-NH-C4-COOH

Boiling Point

712.2±60.0°C at 760 mmHg

Density

1.5±0.1 g/cm3

InChI Key

JUPYDAIBDNUUIF-UHFFFAOYSA-N

InChI

InChI=1S/C18H19N3O6/c22-13-8-7-12(16(25)20-13)21-17(26)10-4-3-5-11(15(10)18(21)27)19-9-2-1-6-14(23)24/h3-5,12,19H,1-2,6-9H2,(H,23,24)(H,20,22,25)

Canonical SMILES

C1CC(=O)NC(=O)C1N2C(=O)C3=C(C2=O)C(=CC=C3)NCCCCC(=O)O

Background Introduction

Pomalidomide-C4-COOH is a specialized E3 ligase ligand-linker conjugate, which integrates the well-characterized E3 ligase binder pomalidomide with a carboxylic acid-functionalized four-carbon linker. This compound serves as a critical intermediate in the development of targeted protein degradation technologies like PROTACs (Proteolysis Targeting Chimeras), designed to harness the body’s own ubiquitin-proteasome system for the selective elimination of disease-causing proteins.

Mechanism

The mechanism of Pomalidomide-C4-COOH centers around its dual-functionality. Pomalidomide acts as a ligand for the E3 ubiquitin ligase CRBN (Cereblon), effectively recruiting the E3 ligase complex when incorporated into bifunctional molecules. The appended C4 aliphatic linker, terminated with a carboxylic acid group, enables facile conjugation to various target protein ligands or other molecular scaffolds. In a PROTAC construct, Pomalidomide-C4-COOH tethers the E3 ligase to a specific target protein, promoting its ubiquitination and subsequent proteasomal degradation.

Applications

Pomalidomide-C4-COOH is widely used in chemical biology and drug discovery as a fundamental building block for synthesizing PROTAC molecules. Its applications include the development of custom PROTACs for degrading oncogenic proteins, creating molecular probes to study protein function, and contributing to the validation of novel therapeutic targets. Researchers select Pomalidomide-C4-COOH due to its reliability, efficiency in E3 ligase recruitment, and ease of chemical modification, making it an essential tool in the toolkit for targeted protein degradation strategies.

• Carboxyl-functionalized linker enables efficient amide bond formation for customized PROTAC assembly.
• Designed for high-affinity CRBN E3 ligase recruitment, optimizing targeted protein degradation strategies.

Stock concentration: *

Desired final volume: *

Desired concentration: *

* 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