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Merck
CN

910481

Pomalidomide-PEG6-butyl CO2H

≥95%

Synonym(s):

1-((2-(2,6-Dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)-1-oxo-3,6,9,12,15,18-hexaoxapentacosan-25-oic acid, Crosslinker–E3 Ligase ligand conjugate, Pomalidomide conjugate, Pomalidomide-2-2-2-2-2-2-6-acid, 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):
C32H45N3O13
Molecular Weight:
679.71
MDL number:
MFCD32669904
UNSPSC Code:
12352101
NACRES:
NA.22

Key Documents

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ligand

pomalidomide

Quality Level

200

Assay

≥95%

form

chunks

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=C3NC(COCCOCCOCCOCCOCCOCCCCCCC(O)=O)=O)=O)NC1=O

InChI

1S/C32H45N3O13/c36-26-10-9-25(30(40)34-26)35-31(41)23-6-5-7-24(29(23)32(35)42)33-27(37)22-48-21-20-47-19-18-46-17-16-45-15-14-44-13-12-43-11-4-2-1-3-8-28(38)39/h5-7,25H,1-4,8-22H2,(H,33,37)(H,38,39)(H,34,36,40)

InChI key

APHLTAOXSKRLNL-UHFFFAOYSA-N

Related Categories

Application

Protein degrader builiding block Pomalidomide-PEG6-Butyl CO2H enables the synthesis of molecules for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. This conjugate contains a Cereblon (CRBN)-recruiting ligand, a linker with both hydrophobic and hydrophilic moieties, and a 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.

Other Notes

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Portal: Building PROTAC® Degraders for Targeted Protein Degradation

Targeted Protein Degradation by Small Molecules

Small-Molecule PROTACS: New Approaches to Protein Degradation

Targeted Protein Degradation: from Chemical Biology to Drug Discovery

Impact of linker length on the activity of PROTACs

Legal Information

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

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000126323

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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
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
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

Articles

Degrader Building Blocks for Targeted Protein Degradation

Protein Degrader Building Blocks are a collection of crosslinker-E3 ligand conjugates with a pendant functional group for covalent linkage to a target ligand.

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