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910511

Sigma-Aldrich

Pomalidomide-C6-PEG3-butyl alkyne

≥95.0%

Synonym(s):

N-(2-(2,6-Dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)-6-(2-(2-(oct-7-yn-1-yloxy)ethoxy)ethoxy)hexanamide, Crosslinker–E3 Ligase ligand conjugate, Pomalidomide conjugate, Pomalidomide-6-2-2-6-alkyne, 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):
C31H41N3O8
Molecular Weight:
583.67
UNSPSC Code:
51171641

ligand

pomalidomide

Assay

≥95.0%

form

(Liquid or Semi-solid or Paste or Solid)

reaction suitability

reaction type: click chemistry
reagent type: ligand-linker conjugate

functional group

alkyne

storage temp.

2-8°C

SMILES string

O=C(C(CC1)N(C2=O)C(C3=C2C=CC=C3NC(CCCCCOCCOCCOCCCCCCC#C)=O)=O)NC1=O

Application

Protein degrader builiding block Pomalidomide-C6-PEG3-butyl alkyne 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 alkyne for click chemistry with an azide 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 alkyne, 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

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Pomalidomide-PEG3-NH2 hydrochloride, ≥95%

901496

Pomalidomide-C6-CO2H, ≥98%

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Pomalidomide-C3-CO2H, ≥95%

901503

(S,R,S)-AHPC-PEG1-Alkyne, ≥95%

901511

(S,R,S)-AHPC-PEG3-NH2 hydrochloride, ≥95%

901504

Pomalidomide-PEG3-CO2H, ≥95%

901517

(S,R,S)-AHPC-PEG2-Alkyne, ≥95%

901516

Pomalidomide-PEG1-NH2 hydrochloride, ≥95%

901513

Pomalidomide-PEG2-NH2 hydrochloride, ≥95%

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(S,R,S)-AHPC-PEG3-Alkyne, ≥95%

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Pomalidomide-PEG3-Alkyne, ≥95%

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Pomalidomide-PEG2-Alkyne, ≥95%

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Pomalidomide-PEG1-CO2H, ≥95%

901526

Pomalidomide-PEG2-CO2H, 95%

901525

Pomalidomide-C9-CO2H, ≥95%

901558

Lenalidomide, ≥95%

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Pomalidomide-PEG6-Alkyne

901834

Pomalidomide-PEG5-Alkyne, ≥95%

901833

Pomalidomide-PEG4-Alkyne

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Pomalidomide-PEG5-NH2 hydrochloride

901829

Pomalidomide-PEG6-CO2H

901828

Pomalidomide-PEG5-CO2H, ≥95%

901824

Pomalidomide-PEG4-CO2H

901860

(S,R,S)-AHPC-PEG6-NH2 hydrochloride, ≥95%

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(S,R,S)-AHPC-PEG5-Alkyne

901851

(S,R,S)-AHPC-PEG4-Alkyne

901850

(S,R,S)-AHPC-PEG5-NH2 hydrochloride

901848

(S,R,S)-AHPC-PEG4-NH2 hydrochloride, ≥95%

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(S,R,S)-AHPC-PEG6-Alkyne

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Pomalidomide-PEG6-butyl azide, ≥95%

903442

Pomalidomide-PEG6-butyl iodide, ≥95%

903833

Pomalidomide-PEG2-azide

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Pomalidomide-PEG1-azide

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(S,R,S)-AHPC-PEG1-azide

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(S,R,S)-AHPC-PEG3-azide, ≥95%

904724

Pomalidomide-PEG2-butyl iodide, ≥95%

904708

Pomalidomide-C6-PEG3-butyl iodide, ≥95%

904678

Pomalidomide-PEG3-azide

904686

Pomalidomide-C6-PEG3-butyl azide, ≥95%

904813

(S,R,S)-AHPC-PEG2-azide

904821

(S,R,S)-AHPC-C6-PEG3-butyl azide, ≥95%

904880

Pomalidomide-C6-PEG1-C3-PEG1-butyl azide, ≥95%

904872

Pomalidomide-PEG2-butyl azide, ≥95%

904864

(S,R,S)-AHPC-PEG6-butyl azide, ≥95%

905178

(S,R,S)-AHPC-C6-PEG1-C3-PEG1-butyl azide, ≥95%

905275

(S,R,S)-AHPC-PEG6-butyl amine hydrochloride, ≥95%

905216

(S,R,S)-AHPC-PEG2-butyl azide, ≥95%

905232

(S,R,S)-AHPC-C6-PEG3-butyl amine hydrochloride, ≥95%

905224

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905399

(S,R,S)-AHPC-PEG2-butyl chloride

905380

(S,R,S)-AHPC-C6-PEG3-butyl chloride, ≥95%

905402

(S,R,S)-AHPC-C6-PEG1-C3-PEG1-butyl chloride, 95%

906050

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906123

(S,R,S)-AHPC-PEG2-butyl amine hydrochloride

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911801

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911690

C5 Lenalidomide, ≥95%

911666

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Pomalidomide-C3-NH2 hydrochloride, ≥95%

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C5 Lenalidomide-PEG1-piperazine hydrochloride, ≥95%

913987

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(S,R,S)-AHPC-alkyne-piperidine hydrochloride

919969

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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
MKCL1552

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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

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Degrader Building Blocks for Targeted Protein Degradation

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

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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