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919462

Sigma-Aldrich

CCW16-PEG5-BocNH

≥95%

Synonym(s):

tert-Butyl (17-(4-(4-(N-Benzyl-2-chloroacetamido)phenoxy)phenoxy)-3,6,9,12,15-pentaoxaheptadecyl)carbamate, Crosslinker-E3 Ligase ligand conjugate, Protein degrader building block for PROTAC® research, RNF4-targeting building block, Template for synthesis of targeted protein degrader

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About This Item

Empirical Formula (Hill Notation):
C38H51ClN2O10
Molecular Weight:
731.27
NACRES:
NA.22

ligand

CCW16

Quality Level

100

Assay

≥95%

form

liquid

reaction suitability

reactivity: carboxyl reactive
reagent type: ligand-linker conjugate

functional group

amine

storage temp.

2-8°C

SMILES string

O=C(CCl)N(CC1=CC=CC=C1)C2=CC=C(C=C2)OC3=CC=C(OCCOCCOCCOCCOCCOCCNC(OC(C)(C)C)=O)C=C3

Application

Protein degrader building block CCW16-PEG5-BocNH enables the synthesis of molecules for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. This conjugate contains a RING finger protein 4 (RNF4)-recruiting ligand, a PEGylated crosslinker, and a pendant amine for reactivity with a carboxylic acid 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 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

Covalent Ligand Screening Uncovers a RNF4 E3 Ligase Recruiter for Targeted Protein Degradation Applications

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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Storage Class Code

10 - Combustible liquids

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

919462-VAR:
919462-50MG:
919462-BULK:

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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
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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