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917303

Sigma-Aldrich

C5 Lenalidomide-C6-PEG1-C3-PEG1-Butyl NH2 hydrochloride

≥95%

Synonym(s):

6-((5-((6-Aminohexyl)oxy)pentyl)oxy)-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)hexanamide hydrochloride, C5 Lenalidomide conjugate, Crosslinker−E3 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):
C30H46N4O6 · xHCl
Molecular Weight:
558.71 (free base basis)
UNSPSC Code:
12352101
NACRES:
NA.22

ligand

C5 Lenalidomide

Quality Level

100

assay

≥95%

form

powder or crystals

reaction suitability

reactivity: carboxyl reactive
reagent type: ligand-linker conjugate

functional group

amine

storage temp.

2-8°C

SMILES string

O=C1N(C2CCC(NC2=O)=O)CC3=CC(NC(CCCCCOCCCCCOCCCCCCN)=O)=CC=C31.Cl

Application

Protein degrader building block C5 Lenalidomide-C6-PEG1-C3-PEG1-Butyl NH2 hydrochloride enables the synthesis of molecules for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. This conjugate contains a Cereblon (CRBN)-recruiting ligand with alternative exit vector, a linker with both hydrophobic and hydrophilic moieties, and a pendant amine for reactivity with an acid on the target warhead. 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 terminal amine, 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

Legal Information

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

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

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

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

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

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

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Pomalidomide-PEG6-butyl azide, ≥95%

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

904651

(S,R,S)-AHPC-PEG3-azide, ≥95%

904724

Pomalidomide-PEG2-butyl iodide, ≥95%

904708

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Pomalidomide-PEG3-azide

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

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

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

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(S,R,S)-AHPC-PEG2-butyl azide, ≥95%

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906050

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(S,R,S)-AHPC-PEG2-butyl alkyne, ≥95%

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911712

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C5 Lenalidomine-C3-NH2 hydrochloride, ≥95%

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C5 Lenalidomide-PEG1-NH2 hydrochloride, ≥95%

911747

C5 Lenalidomide-PEG3-NH2 hydrochloride, ≥95%

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(S,R,S)-AHPC-C3-NH2 hydrochloride, ≥95%

917818

(S,R,S)-AHPC-C9-NH2 hydrochloride, ≥95%

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(S,R,S)-AHPC-C6-NH2 hydrochloride, ≥95%

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C5 Lenalidomide-PEG2-Butyl NH2 hydrochloride, ≥95%

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C5 Lenalidomide-benzyl-piperazine hydrochloride

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C5 Lenalidomide-pyridine-PEG1-piperazine hydrochloride, ≥95%

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Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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

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Degrader Building Blocks for Targeted Protein Degradation

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