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901526

Sigma-Aldrich

Pomalidomide-PEG2-CO2H

95%

Synonym(s):

3-(2-(2-((2-(2,6-Dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)ethoxy)ethoxy)propanoic acid, CrosslinkerE3 Ligase ligand conjugate, Protein degrader building block for PROTAC® research, Template for synthesis of targeted protein degrader

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About This Item

Empirical Formula (Hill Notation):
C20H23N3O8
CAS Number:
Molecular Weight:
433.41
UNSPSC Code:
51171641
NACRES:
NA.22

ligand

pomalidomide

Quality Level

Assay

95%

form

powder or crystals

reaction suitability

reactivity: amine reactive
reagent type: ligand-linker conjugate

functional group

carboxylic acid

storage temp.

2-8°C

SMILES string

O=C(C(CC1)N(C2=O)C(C3=C2C=CC=C3NCCOCCOCCC(O)=O)=O)NC1=O

Application

Protein degrader builiding block Pomalidomide-PEG2-CO2H enables the synthesis of molecules for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. This conjugate contains a Cereblon (CRBN)-recruiting ligand and a PEGylated crosslinker with pendant carboxylic acid for reactivity with an amine on the target ligand. Because even slight alterations in ligands and crosslinkers can affect ternary complex formation between the target, E3 ligase, and PROTAC, many analogs are prepared to screen for optimal target degradation. When used with other protein degrader building blocks with a pendant carboxyl group, parallel synthesis can be used to more quickly generate PROTAC libraries that feature variation in crosslinker length, composition, and E3 ligase ligand.

Automate your CRBN-PEG based PROTACs with Synple Automated Synthesis Platform (SYNPLE-SC002)

Legal Information

PROTAC is a registered trademark of Arvinas Operations, Inc., and is used under license

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Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

901526-VAR:
901526-2.2MG-KC:
901526-BULK:
901526-50MG:


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Momar Toure et al.
Angewandte Chemie (International ed. in English), 55(6), 1966-1973 (2016-01-13)
The current inhibitor-based approach to therapeutics has inherent limitations owing to its occupancy-based model: 1) there is a need to maintain high systemic exposure to ensure sufficient in vivo inhibition, 2) high in vivo concentrations bring potential for off-target side effects, and 3) there is
Kedra Cyrus et al.
Molecular bioSystems, 7(2), 359-364 (2010-10-06)
Conventional genetic approaches have provided a powerful tool in the study of proteins. However, these techniques often preclude selective manipulation of temporal and spatial protein functions, which is crucial for the investigation of dynamic cellular processes. To overcome these limitations
Philipp M Cromm et al.
Cell chemical biology, 24(9), 1181-1190 (2017-06-27)
Traditional pharmaceutical drug discovery is almost exclusively focused on directly controlling protein activity to cure diseases. Modulators of protein activity, especially inhibitors, are developed and applied at high concentration to achieve maximal effects. Thereby, reduced bioavailability and off-target effects can
Daniel P Bondeson et al.
Annual review of pharmacology and toxicology, 57, 107-123 (2016-10-13)
Protein homeostasis networks are highly regulated systems responsible for maintaining the health and productivity of cells. Whereas therapeutics have been developed to disrupt protein homeostasis, more recently identified techniques have been used to repurpose homeostatic networks to effect degradation of

Articles

Partial PROTACs are a collection of crosslinker-E3 ligand conjugates with a pendant functional group for covalent linkage to a target ligand.

Partial PROTACs are a collection of crosslinker-E3 ligand conjugates with a pendant functional group for covalent linkage to a target ligand.

Related Content

Targeted protein degradation (TPD) is an emerging drug discovery strategy that uses small-molecules, such as proteolysis-targeting chimeras (PROTACs), to eradicate targeted proteins linked to disease from cells.

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